Chemistry

Chemistry

Professor Andrew D Abell

Position

Adjunct Professor

Field of Study

Bioorganic / Medicinal Chemistry

Qualifications

B.Sc.(Hons.), Ph.D.(Adel.), M.N.Z.I.C.

Contact Details

andrew.abell@canterbury.ac.nz

Research Group

Postdoctoral Fellows

Dr Matt Jones

Dr Axel Neffe

Dr Steve MacNabb

Dr Shazia Zaman

Dr Paula Brooksby

PhD Students

Kelly Anderson

Mary Gower

Anna McCarthy

Janna Nikkel

Seth Jones

Steve Aitken

Blair Stuart

Andrea Vernall

Nathan Alexander

David Pearson

Hayden Peacock

Jenni Gadd

Barbara Thomson

MSc Students

Mutita Klanchantra

Tom Cain

Research Interests

Abstract
Green Products and ProcessesThe design, synthesis and biological testing of inhibitors of enzymes of mechanistic and therapeutic importance. The target enzymes include chymotrypsin, elastases, dienelactone, hydrolase, HIV-protease, steroid 5alpha-reductase and alpha- and beta-amylases. The synthesis of peptido-mimetics containing latent reactivity and conformational restriction. Studies on the mechanism of dienelactone hydrolase, a key enzyme of the beta-ketoadipate pathway of bacteria and fungi.

Background
Peptides and proteins play a key regulatory role in many biological processes ranging from the transmission of information (chemical messengers) to the catalysis of critical reactions (enzymes). These processes can be studied using peptidomimetics, ie mimics of a peptide that retain many of the biologically important structural features of its parent while possessing a reduced or modified peptidic character. As a result, peptidomimetics have found wide application as enzyme inhibitors and biological probes. For a review see A. D. Abell (editor) Advances in peptidomimetics and amino acid mimics, JAI Press, USA, Volume 1, 1997. Volume 2 is due for release in 1999.

Research

An ability to modulate the reactivity of a molecule is critical to many areas of chemistry, ranging from synthesis to medicinal chemistry. A fine balance exists between the need for useful chemical reactivity and an inherent chemical instability. We are developing peptidomimetics that contain a molecular switch to mask chemical reactivity such that it can be released and utilized on demand. In many cases the conformation or shape of the peptide is also critical to its function, such that it is important to be able to introduce rings and other conformationally rigid elements into these compounds. This work offers the potential to produce new materials designed to carry out important chemical and biochemical transformations.

As an example, we are designing and synthesizing enzyme inhibitors (blockers) with a built in molecular switch that is activated on specific binding to a target enzyme. Once activated, the reactivity is released within the active site to give specific and irreversible inactivation of the enzyme. Serine proteases have proven to be a particularly popular target for many studies in this area, partly because the molecular details of their mechanism of action are so well understood, but also since an over activity of some examples has been implicated in pathological conditions including emphysema, tumor invasion and arthritis. An example of such a system from our work is given below:

Current work in this area is concerned with the design and synthesis of new peptidomimetics that possess latent reactivity and conformational restriction and their use in blocking and studying important biological processes.

  • Alternatively, a molecular switch (for example the trans and cis forms of an azobenzene) can be activated by an external source, such as light, to give a light amplification system suitable for the development of medicinal agents, information storage systems and bioelectronic materials. As an example, the incorporation of this functionality into a suitable peptide provides a photoswitchable inhibitor of an enzyme (see below).

  • We have recently found that some hydroxymethylpyrrole-based peptidomimetics demonstrate an important ability to self assemble through peptide-backbone hydrogen bonding (see X-ray structure below). We now plan to exploit this property to develop new ways of resolving racemic peptides and selecting specified peptide sequences.

 

Postdoctoral Fellowship

  • A two year Marsden funded PhD fellowship is available from the end of 1999. Please enquire for details.
  • If you are a New Zealand citizen and you are looking for a postdoctoral position in bioorganic/medicinal chemistry then please contact me regarding a Foundation for Research, Science and Technology Fellowship. Closing date for applications is the 26th of March.

Current PhD Research Projects

  • Molecular Switches and the modulation of chemical reactivity and enzyme action (Two Marsden Funded PhD fellowships are available commencing 1999 and 2000).
  • The synthesis of macrocyclic peptidomimetics - traditional and combinatorial approaches (Marsden Funded).
  • Peptidomimetic-based inhibitors of serine proteases (Marsden Funded)
  • Template-directed self assembly - the synthesis, structure and biological properties of ion channel models.
  • The design, synthesis and testing of zinc-mediated serine protease inhibitors.

Publications

Selection of:

  • Neffe, A.T. and Abell, A.D.  Developments in the Design and Synthesis of Calpain Inhibitors. Current Opinion in Drug Discovery & Development , 2005 in press.
  • Inhibition studies on salicylate synthase. Payne, Richard J.; Kerbarh, Olivier; Miguel, Ricardo Nunez; Abell, Andrew D.; Abell, Chris. Org. Biomol. Chem. 2005 , 3(10), 1825-1827.
  • Design and synthesis of aromatic inhibitors of anthranilate synthase Richard J. Payne, Miguel D. Toscano, Esther M. M. Bulloch, Andrew D. Abell and Chris Abell,  Org. Biomol. Chem. 2005 , 3(12), 2271-1281.
  • Synthesis of trisubstituted imidazoles by Palladium-catalysed cyclisation of O-pentafluorobenzoylamidoximes: application to amino acid mimetics with a C-terminal imidazole . Shazia Zaman, Kitamura Mitsuru , and Andrew D. Abell . Org. Lett. 2005 , 7(4), 609-611.
  • Olefin Metahthesis: catalyst development, microwave catalysis and domino applications. S. G. Aitken; Abell, A. D. Aust. J. Chem. 2005 , 58, 3-13 (invited review).
  • Removal of the nitro- and phenyl groups from NPPB decreases its inhibitory effect on cytoplasmic streaming in the alga Nitella hookeri. Graichen, F.; Giles, K. R.; Abell, A. D.; Garrill, A. Biochem. Cell Biol., 2005 , 83 (2), 133-139.
  • A. D. Abell, Aust. J. Chem . 2004 , 57, volume editor.  
  • The synthesis, testing and development of a -(hydroxymethyl)pyrroles as DNA binding agents, Derek C. Martyn and Andrew D. Abell , Aust. J. Chem . 2004 , 57 , 1073-1077.  
  • Synthesis and Evaluation of Eight-Membered cyclic Pseudo-Dipeptides, Abell, Andrew D.; Brown, Karina M.; Coxon, James M.; Jones, Matthew A.; Miyamoto, Sigeru; Neffe, Axel T.; Nickel, Janna M; Stuart, Blair G, Peptides , 2005 , 26(2), 251-258.  
  • Cross-metathesis coupling of sugars and fatty acids to lysine and cysteine, Andrea J. Vernall and Andrew D. Abell , Organic & Biomolecular Chemistry 2004 , 2, 2555-2557.  
  • Inhibitors of Types I and II Dehydroquinase. C. Le Sann, M. A. Gower and A. D. Abell , Mini Reviews in Med. Chem., 2004 , 7(4), 747-756 (invited, cover issue).
  • Synthesis and protein conjugation studies of vitamin K analogues. Richard J. Payne, Alison M. Daines, Bruce M. Clark and Andrew D. Abell. Bioorganic and Medicinal Chemistry , 2004 , 12, 5785-5791.
  • Peptidic Aldehydes Based on a - and b -Amino Acids: Synthesis, Inhibition of m-Calpain and Anti-cataract Properties. Richard J. Payne, Karina M. Brown, James M. Coxon, James D. Morton, Hannah Yun-Young Lee and Andrew D. Abell . Aust. J. Chem . 2004 , 57 , 877-884.
  • The preparation of side chain functionalized analogues of coenzyme Q for protein conjugation studies. Alison M. Daines and Andrew D. Abell , Organic & Biomolecular Chemistry 2004 , 2(16), 2371-2375.
  • Synthesis and Solid State Structure of Phenylalanine-Containing Mimetics Constrained in a Proline-Like Conformation. James Gardiner and Andrew D. Abell , Organic & Biomolecular Chemistry , 2004 , 2(16), 2365-2370.
  • Synthesis and X-ray structure of functionalised proline mimics. James Gardiner and Andrew Abell , Arkivoc , 2004 , Issue in Honour of Rod Richards, ms. x, 46-52.
  • The Synthesis of Cyclic b -Amino Acids from Methionine, Allylglycine and Serine, James Gardiner, Kelly H. Anderson, Alison Downard, and Andrew D. Abell , J. Org. Chem ., 2004 , 69(10), 3375-3382.
  • Synthesis and Properties of ArgoGel-OMs. C. Le Sann and A. D. Abell , Aust. J. Chem ., 2004 , 57(4), 355-358.
  • Cross Metathesis of Nitrogen-Containing Systems. A. J. Vernall and A. D. Abell Aldrichimica Acta , 2003 , 36(3), 93-105 (invited).
  • The Synthesis of Naturally Occurring Vitamin K and Vitamin K Analogues. A. M. Daines, R. J. Payne, M. E. Humphries, A. D. Abell , Current Organic Chemistry , 2003 , 7(16), 1625-1634 (invited).
  • Ring-deactivated hydroxyalkylpyrrole-based inhibitors of a -chymotrypsin: synthesis and mechanism of action. D. C. Martyn, A. J. Vernall, B. M. Clark, A. D. Abell, Organic & Biomolecular Chemistry , 2003 , 1(12), 2103-2110.
  • A diastereoselective synthesis of the tetrahydropyridazinone core of 2-oxo-1,6-diazobicyclo [4.3.0] nonane-9-carboxylate-based peptidomimetics starting from (S)-phenylalanine. J. Gardiner, A. D. Abell , Tetrahedron Letters , 2003 , 44(22), 4227-4230.
  • A convenient method for the synthesis of dehydroquinic acid. C. Le Sann, C Abell, A. D. Abell, Synthetic Communications , 2003 , 33(4), 527-533.
  • A. D. Abell, Pure and Applied Chemistry 2003 , 75(1), volume editor.
  • Synthesis of Functionalized Piperidinones. M. E. Humphries, J. Murphy, A. J. Phillips, A. D. Abell , J. Org. Chem ., 2003 , 68(6), 2432-2436.
  • The synthesis of NPPB and NPBB by reductive amination and the effects of these compounds on K+ channels of the alga Nitella hookeri. K. R. Giles, M. Humphries, A. D. Abell, A. Garrill , Bioorganic & Medicinal Chemistry Letters , 2003 , 13(2), 293-295
  • Synthesis of Substituted Cyclohexenyl-Based b -Amino Acids by Ring Closing Metathesis. A. D. Abell and J. Gardiner, Org. Lett., 2002 , 4, 3663-3666.
  • A simple method for the preparation of 3-hydroxyiminodehydroquinate, a potent inhibitor of type II dehydroquinase. C. Le Sann , C. Abell and A. D. Abell , J. Chem. Soc., Perkin Trans. 1, 2002 , 2065-2068.
  • Protein Binding Studies of Vitamin K analogues for use in an immunological assay. R. J. Payne and A. D. Abell , Chemistry in New Zealand , 2002 , 16-20.
  • A convenient method for the synthesis of dehydroquinic acid, C. Le Sann , C. Abell and A. D. Abell , Synthetic Communications , 2002 , 2065-2068.
  • Heterocyclic-Based Peptidomimetics, A.D. Abell , Letters in Peptide Science , 2001 , 8, 267-272.
  • An amino acid N -derivatising group that can be colored on demand, A. D. Abell , D. C. Martyn, B. C. H. May and B. K. Nabbs, Tetrahedron Letters, 2002 , 43, 3673-3675.
  • a -Methylene tetrazole-based peptidomimetics: synthesis and inhibition of HIV protease, B. C. H. May, and A. D. Abell , J. Chem. Soc., Perkin Trans. 1, 2002 , 172-178.
  • Stereocontrol of the Horner-Wadsworth-Emmons reaction: Application to the synthesis of HIV-1 protease inhibitors, D. C. Martyn, D. A. Hoult, and A. D. Abell , Aust. J. Chem. , 2001 , 54 (6): 391-396.
  • The synthesis and solid state structure of (8S)-8-benzyl-8,9-dihydro-7H-tetrazolo [1,5-d] [1,4] diazepin-6-one, B. C. H. May, and A. D. Abell , Chem. Commun ., 2001 , (20): 2080-2081.
  • New Herbicidal and Antimicrobial Agents that Inhibit the Shikimate Pathway, M. A. Gower and A. D. Abell , New Zealand Science Review , 2001 , 58 (3), 87-90..
  • a -Ketoester-based Photobiological Switches: Synthess, Peptide Chain Extension and Asay Against a -Chymotrypsin, A. J. Harvey and A. D. Abell , Bioorganic & Medicinal Chemistry Letters , 2001 , 11(18), 2441-2444.
  • The synthesis and crystal structure of alpha-keto tetrazole-based dipeptide mimics, B. C. H. May, A. D. Abell , Tetrahedron Letters, 2001 , 42 , 5641-5644.
  • The Design and Synthesis of a Conformationally Restricted trans Peptide Isostere Based on the Bioactive Conformations of Saquinavir and Nelfinavir, Michael K. Edmonds and Andrew D. Abell, J. Org. Chem ., 2001 , 66 , 3747-3752.
  • Synthesis, X-ray and conformational studies of novel tetrazole-containing macrocycles: 4,13-dioxa-1,7,8,9,17,18,19,20-octaazatricyclo [14.2.1.17,10] icosa-8,10(20),16(19),17-tetraene and 4,14-dioxa-1,7,8,9,10,18,19,20-octaazatricyclo [15.2.1.07,10] icosa-8,10,17(20),18-tetraene , V. Y. Zubarev, R. E. Trifonov, V. V. Filichev, V. A. Ostrovskii , M. K. Edmonds and A. D. Abell , J. Chem. Soc., Perkin Trans. 2 , 2001 , 3, 417-421.
  • Ring-deactivated Hydroxymethylpyrroles as Inhibitors of a -Chymotrypsin, A. D. Abell and B. K. Nabbs, Bioorganic & Medicinal Chemistry, 2001 , 9(3), 621-628.
  • Azobenzene-Containing, Peptidyl a -Ketoesters as Photobiological Switches of a -Chymotrypsin, A. D. Abell and A. J. Harvey, Tetrahedron , 2000 , 56, 9763-9771. (invited paper for a special issue of Tetrahedron ).
  • Simple bi- and tricyclic inhibitors of human steroid 5 a -reductase, A. D. Abell , M. J. Prince, A. M. McNulty and B. L. Neubauer, Bioorganic & Medicinal Chemistry Letters, 2000 , 10(17), 1909-1911.
  • Kinetic Characterisation of Ene-Diol-Based Inhibitors of a -Amylase, J. A. Gerrard , M. J. Prince and A. D. Abell , Bioorganic & Medicinal Chemistry Letters , 2000 , 10(14), 1575-1576.
  • Progress Towards an Intramolecular Diels-Alder–Ring-Expansion Approach to Taxinine: The Interplay of Lewis Acids and High-Pressure, A. J. Phillips, J. C. Morris, and A. D. Abell , Tetrahedron Lett., 2000 , 41 , 2723-2727.
  • Ring-closing Metathesis of nitrogen-containing compounds: applications to heterocycles, alkaloids and peptidomimetics; A. J. Phillips and A. D. Abell , Aldrichimica Acta , 1999 , 32(3), 75-89.
  • The synthesis and x-ray crystal structure of phenylalanine-based N-benzyloxysuccinimides, A. D. Abell , M. D. Oldham, M. M. Moore, W. T. Robinson, Aust. J. Chem ., 1999 , 52(10), 977-981.
  • Properties and reactions of ring-deactivated deuterated hydroxymethylpyrroles, A. D. Abell and B. K. Nabbs, Org. Lett. , 1999 , 1 , 1403-1405.
  • Synthesis of lactam-based peptidomimetics from b -keto esters and b -keto amides, A. D. Abell and J. Gardiner, J. Org. Chem., 1999 , 9668-9672.
  • A convenient preparation of (2SR,3S)-3-amino-2-hydroxy-4-phenylbutanoic acid: An important peptide bond isostere, B. C. H. May and A. D. Abell , Synth. Commun , 1999 , 29(14), 2515-2525.
  • Leucine-phenylalanine dipeptide-based N mesyloxy-succinimides: Synthesis of all four stereoisomers and their assay against serine proteases, A. D. Abell and M. D. Oldham, Bioorganic & Medicinal Chemistry Letters , 1999 , 9 , 497-500.
  • The synthesis and P388 cytotoxicity of mycalazol 11 and related 5-acyl-2-hydroxymethylpyrroles, B. K. Nabbs and A. D. Abell , Bioorganic & Medicinal Chemistry Letters , 1999 , 9 , 505-508.
  • Succinimide and saccharin-based enzyme-activated inhibitors of serine proteases, D. C. Martyn, M. J. B. Moore and A. D. Abell , Current Pharmaceutical Design , 1999 , 405-415.
  • The preparation and biological activity of lactam-based, non-steroidal, inhibitors of human type-1 steroid 5alpha-reductase, A. D. Abell , A. J. Phillips, S. Budhia, A. M. McNulty and B. L. Neubauer, Aust. J. Chem. , 1998 , 51 , 389-396.
  • The synthesis and properties of ring-deactivated deuterated hydroxymethylpyrroles, A. D. Abell , B. K. Nabbs, A. R. Battersby, J. Am. Chem. Soc. , 1998 , 120, 1741-1746. (see Chemtracts-Org. Chem., 1999 , 534 for an independent review of this paper).
  • 1 HNMR study of the hydrolysis of N -acylhydroxy [ 2 H] pyrroles, A. D. Abell and B. K. Nabbs, J. Chem. Soc., Chem. Commun. , 1998 , 8, 919-920.
  • Ascorbic acid-based inhibitors of a -amylases, A. D. Abell , M. J. Ratcliffe and J. Gerrard, Bioorganic & Medicinal Chemistry Letters , 1998 , 8 , 1703-1706.
  • The reaction of N -magnesium derivatives of pyrroles with N -mesylchloromethylpyrroles: A synthesis of dipyrrylmethanes, A. D. Abell , B. K. Nabbs, A. R. Battersby, J. Org. Chem., 1998 , 63, 8163-8169.
  • Drug design: The synthesis of conformationally restricted HIV protease inhibitors, A. D. Abell and B. C. H. May, Russian Journal of HIV/AIDS and Related Problems , 1998 , 2(3), 79-81.
  • Synthesis and X-ray structure of a 1,2,3,6-tetrahydropyridine-based phenylalanine mimetic, A. D. Abell , J. G. Gardiner, A. J. Phillips and W. T. Robinson, Tetrahedron Lett. 1998 , 9563-9566.
  • Taxane anti-cancer compounds, A. J. Phillips and A.D. Abell, Chemistry in New Zealand , 1997 , 61 , 7-9.
  • The synthesis and X-ray crystallographic structure of leucine-phenylalanyl succinimide-based pseudopeptides, A. D. Abell and M. D. Oldham, J. Org. Chem. , 1997 , 62 , 1509-1513.
  • Nuclear magnetic resonance characterization of 6 a -chloro-5 b -cholestane-3 b ,5-diol formed from the reaction of hypochlorous acid with cholesterol , A. C. Carr, C. C. Winterbourn, J. Blunt, A. J. Phillips and A. D. Abell , Lipids, 1997 , 32 , 363-367.
  • Chemistry of the mycalamides: Antiviral and antitumour compounds from a New Zealand marine sponge. Part 6. The synthesis and testing of analogues of the C7-C10 fragment, A. D. Abell , J. W. Blunt, G. J. Foulds and M. H. G. Munro, J. Chem. Soc. Perkin Trans. 1, 1997 , 1647-1654.
  • The chemistry and X-ray crystallographic structure of N-protected (5-oxo-1,3-oxazolidin-4-yl)acetic acids: Versatile intermediates in the synthesis of peptidomimetics, A. D. Abell , R. A. Edwards and M. D. Oldham, J. Chem. Soc. Perkin Trans. 1, 1997 , 1655-1662.
  • The preparation and biological activity of tricyclic non-steroidal inhibitors of human steroid 5 a -reductase, A. D. Abell , M. Brandt, M. A. Levy and D. A. Holt, J. Chem. Soc. Perkin Trans. 1, 1997 , 1663-1667.
  • Synthesis of a cis -conformationally restricted peptide bond isostere and its application to the inhibition of the HIV-1 protease, A. D. Abell and G. Foulds, J. Chem. Soc. Perkin Trans. 1, 1997 , 2475-2482.
  • Simpe cis -epoxide-based inhibitors of HIV-1 protease, A. D. Abell , D. A. Hoult, D. A. Bergman, D. P. Fairlie, Bioorganic & Medicinal Chemistry Letters , 1997 , 7, 2853-2856.
  • X-Ray molecular structures of (2R,4S,1'S)-3-benzoyl-4-benzyl-4- [(1'-benzoylamino)benzyl] -2-phenyl-1,3-oxazolidin-5-one, (2R,4S,1'S)- and (2R,4S,1'R)-3-benzoyl-4- [(1'-benzoylamino)benzyl] -4-methylethyl-2-phenyl-1,3-oxazolidin-5-one, A.D. Abell , M.D. Oldham and J.M. Taylor, J. Chem. Soc. Perkin Trans. 1, 1996 , 1299-1304.
  • The preparation and evaluation of (+/-)-trans-1-diazo-8-methoxy-4a-methyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-2-one as an inhibitor of human type-1 steroid 5 a -reductase, A.D. Abell , M. Brandt, M.A. Levy and D.A. Holt, Bioorganic & Medicinal Chemistry Letters , 1996 , 6 , 883-884.

 

  • A comparison of steroidal and non-steroidal inhibitors of human steroid 5 a -reductase: New tricyclic aryl acid inhibitors of the type-1 isozyme, A.D. Abell , M. Brandt, M.A. Levy and D.A. Holt, Bioorganic & Medicinal Chemistry Letters , 1996 , 6 , 481-484.
  • The 1994 NZIC Easterfield award invited article: The inhibition of steroid 5 a -reductase, A.D. Abell and B.R. Henderson, Chemistry in New Zealand , 1996 , 60 , 32-35.
  • Steroidal and non-steroidal inhibitors of steroid 5 a -reductase, A.D. Abell and B.R. Henderson, Current Medicinal Chemistry , 1995 , 2 , 583-597.
  • Benzophenone- and indolecarboxylic acids: Potent type-2 specific inhibitors of human steroid 5 a -reductase, D.A. Holt , D.S. Yamashita, A.L. Konialian-Beck, Y.I. Luengo, A.D. Abell , D.J. Bergsma, and M.A. Levy. J. Med. Chem. , 1995 , 38 , 13-15.
  • The synthesis of phenylalanine-based cyclic acylated enaminoester dipeptide analogues: Inhibitors of a -chymotrypsin. X-ray molecular structure of (2'S,4'R)-4'-benzyl-3'-benzyloxycarbonyl-5'-oxo-2'-phenyloxazolidin-4'-ylacetic acid, A.D. Abell , M.D. Oldham and J.M. Taylor J. Chem. Soc. Perkin Trans. 1, 1995 , 953-962.
  • The synthesis of cyclic acylated enaminoesters from enollactones, 4-keto-amides and 5-hydroxylactams, A.D. Abell , M.D. Oldham and J.M. Taylor. J. Org. Chem., 1995 , 60 , 1214-1220.
  • Preparative chiral HPLC separation of all possible stereoisomers of LY191704 and LY266111 and their in vitro inhibition of recombinant human types 1 and 2 steroid 5 a -reductase, A.D. Abell , D.A. Holt, K.F. Erhard, H-K Yen, D.S. Yamashita, M. Brandt, H. Mohammed and M.A. Levy. Bioorganic & Medicinal Chemistry Letters., 1994 , 4 , 1365-1368.
  • A non-steroidal diene acid inhibitor of human type 2 steroid 5 a -reductase, A.D. Abell , M. Brandt, M.A. Levy and D.A. Holt. Bioorganic & Medicinal Chemistry Letters , 1994 , 4 , 2327-2330.
  • Fast atom bombardment mass spectra of keto acid and keto ester phosphoranes, A.D. Abell , B.M. Clark, K.B. Morris, J.M. Taylor and G.J. Wright. Org. Mass Spectrom. , 1993 , 28 , 27-29.
  • Synthesis of acylated enaminoester dipeptide analogues via the bromination of a keto acid phosphorane, A.D. Abell and J.M. Taylor. J. Org. Chem., 1993 , 58 , 14-15.
  • Halolactonization of keto acid phosphoranes: Synthesis of halo enol lactones, A.D. Abell , D.A. Hoult, K.M. Morris, J.M. Taylor and J.O. Trent. J. Org. Chem., 1993 , 58 , 1531-1537.
  • Synthesis and amino acid chain extension of 1-acylated hydroxymethylpyrroles, A.D. Abell and J.C. Litten. Aust. J. Chem. , 1993 , 46 , 1473-1483.
  • Synthesis and hydrolysis of phenylalanine-proline analogues with latent reactivity A.D. Abell and J.C. Litten. Tetrahedron Lett ., 1992 , 3005-3008.
  • Synthesis of 1,2-disubstituted pyrroles: A cis peptide surrogate, A.D. Abell , D.A. Hoult and E.J. Jamieson. Tetrahedron Lett., 1992 , 5831-5832.
  • Reactions of 1,4-dimethyl-4-nitrocyclohexa-2,5-dien-1-yl acetates with nitrogen dioxide; the formation of polynitro cyclohexenyl esters, A.D. Abell, M.P. Hartshorn, M.E . Maclennan, W.T. Robinson and G.J. Wright. Aust. J. Chem., 1991 , 44 , 43-51.
  • Carboxyl-to-ketone dimeric and catemeric hydrogen bonding in a keto acid phosphorane: X-ray structure of 6-ethoxycarbonyl-5-oxo-6-(triphenylphosphoranylidene)hexanoic acid, 33. A.D. Abell , J.O. Trent and W.T. Robinson. J. Chem. Soc. Chem. Commun. , 1991 , 362-363.
  • A combined X-ray crystallographic and infrared and Raman spectroscopic study of hydrogen bonding patterns in keto acid phosphoranes, A.D. Abell , J.O. Trent and K.B. Morris. J. Chem. Soc. Perkin Trans. 2 , 1991 , 1077-1083.
  • A single crystal X-ray analysis of a novel intramolecular hydrogen bonded biphenyl phosphorane, A.D. Abell , K.B. Morris and V. McKee, Aust. J. Chem., 1990 , 43 , 765-771.
  • Synthesis and deprotection of 1-ethoxycarbonyl-4-diphenyl-methoxycarbonyl-1-methyl-2-oxobutyltriphenylphosphonium chloride: A key intermediate in the Wittig reaction between a cyclic anhydride and a stabilized ylide, A.D. Abell , K.B. Morris and J.C. Litten. J. Org. Chem., 1990 , 55 , 5217-5221.
  • A novel bromo lactonization of acylated phosphoranes. A new route to bromo enol lactones, A.D. Abell and J.O. Trent, J. Chem. Soc. Chem. Commun. , 1989 , 409.
  • Low temperature nuclear magnetic resonance study of the acylation of a stabilized ylide: C- vs O-Acylation, A.D. Abell , J.O. Trent and B.I. Whittington, J. Org. Chem. , 1989 , 54 , 2762.
  • Structural investigations of phosphoranes. A single-crystal X-ray analysis of 1-ethoxycarbonyl-2-oxopropylidenetriphenylphosphorane, A.D. Abell , B.M. Clark and W.T. Robinson, Aust. J. Chem. , 1989 , 42 , 1161.
  • Reactions of 4-methyl-1-methylethyl-4-nitrocyclohexa-2,5-dien-1-yl acetates with nitrogen dioxide; towards a mechanism for the formation of polynitro cyclohexenyl esters on reaction of p -cymene with nitrogen dioxide in acetic anhydride, A.D. Abell , M.P. Hartshorn, W.T. Robinson, A.G. Waller and G.J. Wright, Aust. J. Chem. , 1989 , 42 , 2225-2242.
  • A mechanistic study of the Wittig reaction between a cyclic anhydride and a stabilized phosphorane, A.D. Abell , B.M. Clark and W.T. Robinson, Aust. J. Chem. , 1988 , 41 , 1243.
  • Stereochemistry of formation of the hydroxymethyl group of hydroxymethylbilane, the precursor of uro'gen-III, J-R Schauder, S. Jendrezejewski, A.D. Abell, G.J. Hart and A.R. Battersby , J. Chem. Soc. Chem. Commun. , 1987 , 436.
  • Synthesis of dialkyl hex-2-yne-1,6-dioates and hept-2-yne-1,7-dioates, A.D. Abell, G.W. Heinicke and R.A. Massy-Westropp, Synthesis , 1985 , 764.
  • Regioselective bond cleavage and coordination effects in the reduction of some acetals with lithium in ammonia, A.D. Abell and R.A. Massy-Westropp, Tetrahedron , 1985 , 41 , 2451.
  • Mechanism of acetal cleavage with methylmagnesium iodide, A.D. Abell and R.A. Massy-Westropp, Aust. J. Chem. , 1985 , 38 , 1031.
  • Rearrangement of freelingyne with base, A.D. Abell, R.A. Massy-Westropp and G.D. Reynolds, Aust. J. Chem. , 1985 , 38 , 1129.
  • Eremophilane and serrulatane terpenoids from Eremophila rotundifolia , A.D. Abell and R.A. Massy-Westropp, Aust. J. Chem. , 1985 , 38 , 1263.
  • The structure of a stable serrulatane diterpenoid acetal from Eremophila rotundifolia , A.D. Abell, E. Horn, G.P. Jones, M.R. Snow, R.A. Massy-Westropp and R. Riccio, Aust. J. Chem. , 1985 , 38 , 1837.
  • Stereospecific formation of tetrahydrofurans from substituted 2,8-dioxabicyclo [3.2.1] oct-3-ylmethanols, A.D. Abell, E. Dimitriadis and R.A. Massy-Westropp, Aust. J. Chem. , 1984 , 37 , 395.
  • Aspects of the mechanism of the Wittig reaction between cyclic anhydrides and stabilized phosphoranes, A.D. Abell and R.A. Massy-Westropp, Aust. J. Chem. , 1982 , 35 , 2077.
  • The Wittig reaction with glutaric and succinic anhydrides, A.D. Abell, I.R. Doyle and R.A. Massy-Westropp, Aust. J. Chem. , 1982 , 35 , 2277.  

Books Edited

  • Abell, A. D. editor 'Advances in Peptidomimetics and amino acid mimics', JAI Press, USA, Volume 2, 1999 , 300 pages.
  • Abell, A. D. editor 'Advances in Peptidomimetics and amino acid mimics', JAI Press, USA, Volume 1, 1997 , 302 pages.

Book chapters and contributions to Books

  • The Wittig and Related Reactions, M. K. Edmonds, A. D. Abell. In Modern Carbonyl Elimination, T. Takeda (Ed), Wiley-VCH, 2004, pp 1-16.
  • Wittig and related reactions. In Organophosphorus reagents; a practical approach, A. D. Abell, and M. J. Edmonds (Ed P. J. Murphy, Oxford University press), 2004, pp 99-127.
  • Triethyl phosphonoacetate. In "Encyclopedia of Reagents for Organic Synthesis" Abell, A.D. (Ed. L.A. Paquette, John Wiley and Son), 1995 , 5116-5118.
  • Trimethyl phosphonoacetate. In "Encyclopedia of Reagents for Organic Synthesis" Abell, A.D ., Taylor , J.M. (Ed. L.A. Paquette, John Wiley and Son), 1995 , 5220-5223.
  • Dimethyl methylphosphonate. In "Encyclopedia of Reagents for Organic Synthesis" Abell, A.D. (Ed. L.A. Paquette, John Wiley and Son), 1995 , 2098-2110.
  • Dimethyl bis(methylthio)methylphosphonate. In "Encyclopedia of Reagents for Organic Synthesis" Abell, A.D. , Taylor , J.M. (Ed. L.A. Paquette, John Wiley and Son), 1995 , 2031-2033.
  • Latent reactivity: The study of enzyme mechanisms and the design of enzyme inactivators in Advances in Detailed Reaction Mechanisms A.D. Abell. (Ed. J.M. Coxon), Vol 2, JAI Press , Connecticut USA , 1992 , pp 243-278.

Patents

  • Diazo-phenanthrenone-based inhibitors of steroid 5-alpha reductase. Abell, A.D., Holt, D.A. International Application No. PCT/US95/04599, 1995 .

Refereed Conferences proceedings

  • Design, synthesis and evaluation of peptidomimetic inhibitors of proteases. Abell, A. D. Fukuoka Japan , Peptide Science 2004 , in press.
  • Conformationally constrained b -amino acids. Anderson, K. H.: Gardiner, J.; Abell, A. D. Peptides 2004 : Proceedings of the Twenty-Seventh European Peptide Symposium, The Japanese Peptide Society, Y. Shimohigashi (Ed), pp 63-67.
  • Cross metathesis reactions of amino acids. Vernall, A. J.; Abell, A. D. Peptides 2004 : Proceedings of the Twenty-Seventh European Peptide Symposium, in press.
  • Synthesis of shikimate pathway inhibitors as potential antimicrobial agents. Gower MA, Le Sann C, Abell AD ABSTR PAP AM CHEM S 226: 339-MEDI Part 2 SEP 2003.
  • Peptidomimetics; control of chemical shape. The synthesis of cyclic beta-amino acids using ring-closing metathesis. A. D. Abell , J. Gardner, Peptides 2002 : Proceedings of the Twenty-Seventh European Peptide Symposium, (Ed. E. Benedetti, C. Pedone) 14-15. 
  • An amino acid protecting group that can be colored on demand, A. D. Abell , B. C. H. May and B. K. Nabbs, Peptides 2000 : Proceedings of the Twenty-Sixth European Peptide Symposium, (Ed. J. Martinez, J.-A. Fehrentz) 285-286.

Conference Papers and Presentations (last 10 years only)

  • 'Synthesis and Modelling Studies of Peptidomimetic Calpain Inhibitors for Cataract Treatment' Neffe, A.T., Jones, M.A., Stuart, B.G., Abell, A.D., Coxon, J.M., Payne, R.J., Myamoto, S., Lee H. Y.-Y., Robertson, L.J.G., Morton, J.D. Annual Meeting of the Society of German Chemists, Dusseldorf (11-14 Sept 2005)
  • Kelly Anderson, Alison Downard, Paula Brooksby, Andrew Abell. 40th IUPAC Congress held in Beijing , China , August 2005.
  • Biochemistry, Where has the chemistry gone? Andrew D. Abell. Christchurch School of Medicine, July 2005.
  • Drug design and discovery at Canterbury , cataract formation and treatment. Korean University Delegation, Christchurch , June 2005
  • Drug design and discovery at Canterbury . Andrew D. Abell. MoRST delegation to Riken Institute, Tokyo , Japan , May 2005. 39 th ACS Organic Divisional meeting, University of Utah , Salt Lake City , June 2005.
  • The Synthesis of Cyclic b -Amino Acids from Methionine, Allylglycine and Serine . Andrew D. Abell, Kelly H. Anderson, and James Gardiner. 39 th ACS Organic Divisional meeting, University of Utah , Salt Lake City , June 2005.
  • Cross Metathesis of Sugars and Fatty Acids with Lysine and Cysteine. Andrew D. Abell and Andrea J. Vernall. 39 th ACS Organic Divisional meeting, University of Utah , Salt Lake City , June 2005.
  • Synthesis and modeling studies of peptidomimetic aldehydes related to a cataract preventing calpain inhibitor, Neffe, A.T.*, Abell, A.D., Coxon, J.M., Jones, M.A., Myamoto, S., Nikkel, J.M., Payne, R.J., and Stuart, B.G.: 6th winter conference on Bioorganic and Medicinal Chemistry, Steamboat Springs, Colorado (23-28th Jan 2005).
  • The synthesis and biological properties of conformationally constrained peptidomimetics. Andre Abell. Nove 2004. Plenary lecture: 1st Asia-Pacific International peptide Symposium, Fukuoka, Japan.
  • Synthesis of Calpain Inhibitors containing a Eight-Membered cyclic Pseudo-dipeptide James M. Coxon, Andrew D. Abell, Sigeru Miyamoto, Blair G. Stuart, Axel T. Neffe, Matthew A. Jones. Invited lecture: 2004 July ISMC / RACIOC Chemistry Conference
  • Cataracts; Development of Inhibitors. James M. Coxon, Andrew D. Abell, Sigeru Miyamoto, Blair G. Stuart, Axel T. Neffe, Matthew A. Jones. Invited lecture: Chemistry Biology Interface: Synergistic New Frontiers CBISNF-2004. Nov 21-26 New Delhi .
  • Anderson, Kelly H.; Abell, Andrew D. FiRST Fellows and Scholars Seminar, Auckland , 22 June, 2004.  Conformationally Constrained Amino Acids.
  • Anderson, Kelly H; Gardiner, James; Abell, Andrew D.  3rd International and 28th European Peptide Symposium Prague , Czech Republic , September 5-10, 2004.  Conformationally Constrained â - Amino Acids.
  • Florian H.M. Graichen, Michael K. Edmonds and Andrew D. Abell. 20th Royal Australian Chemical Institute Organic Chemistry Conference, Cairns , Australia , July 4-8, 2004. New Strategy for the Stereoselective Synthesis of Fluorinated beta-amino acids.
  • Vernall, A.J; Abell, A.D; FRST Seminar, Auckland , 22 June, 2004. Joining peptides to target molecules.
  • Vernall, A.J; Abell, A.D; RACIOC Chemistry Conference, Cairns , July 4-8, 2004. Metathesis reactions with amino acids.
  • Vernall, A.J; Abell, A.D; 3rd International and 28th European Peptide Symposium, Prague , September 5-10, 2004. Metathesis reactions with amino acids.
  • Cain, T.P.; Shigeru, M.; Abell, A.D.; Coxon J.M. New Zealand Institute of Chemistry Conference, Nelson, 30 November-4 December, 2003. Design and Synthesis of Cyclic Analogues of SJA6017
  • Karina M. Brown and Andrew D. Abell New Zealand Institute of Chemistry Conference, Nelson, 30 November-4 December, 2003. Improving the Bioavailability of Calpain Inhibitors via Host-Guest Chemistry with Cyclodextrins
  • Anna R. McCarthy, Andrew D. Abell, Ian C. Shaw. New Zealand Institute of Chemistry Conference, Nelson, 30 November-4 December, 2003. Structure-Activity Relationships of Xenoestrogens Determined by a Yeast Estrogen Screen (YES).
  • Janna M. Nikkel, Emma M. Turner, Andrew D. Abell . New Zealand Institute of Chemistry Conference, Nelson, 30 November-4 December, 2003. The Design and Synthesis of Calpain Inhibitors as a Treatment for Cataract
  • Mary Gower, Christine Le Sann and Andrew Abell. New Zealand Institute of Chemistry Conference, Nelson, 30 November-4 December, 2003. Design and Synthesis of Dehydroquinase Inhibitors
  • Nathan Alexander, David Pearson, Andrew Abell. New Zealand Institute of Chemistry Conference, Nelson, 30 November-4 December, 2003. Synthesis of unsymmetrical 3,4'- and 4,4'-disubstituted azobenzenes and their potential applications.
  • Florian Graichen, Khris Giles, Ashley Garril, Andrew Abell. New Zealand Institute of Chemistry Conference, Nelson, 30 November-4 December, 2003. The synthesis of NPPB and NPPB analogues by reductive amination and the effect of these compounds on cytoplasmic streaming.
  • Andrew Abell. Invited lecture. 5 th Australian peptide Conference, Daydream Island , Oct 5-10, 2003. From Discovery to Therapeutics.
  • James Gardiner, Andrew Abell.The 2003 New Zealand Institute of Chemistry Conference, Nelson, 30 November-4 December, 2003. Thrombin Inhibition: A Diastereoselective Synthesis of an Important Class of Dipeptide beta-Strand Mimetic,
  • Andrew Abell, Plenary lecture the 19 th Royal Australian Chemical Institute (RACI) Organic Conference, Lorne , Australia (6-11 July 2003). Conformationally constrained and Immobilised Peptidomimetics
  • Andrew Abell, Invited address to Otago University Department of Chemistry, July, 2002. Peptidomimetic inhibitors of proteases.
  • Andrew Abell, Invited address to Otago University Department of Biochemistry, June 18, 2002. Mimicking Nature's Biomolecules: From Enzyme Inhibitors to Molecular Scaffolds.
  • Michael K Edmonds and Andrew D Abell, IUPAC/ICOS-14 Conference, Christchurch , July 2002. The Asymmetric Synthesis of Chiral Fluoro Compounds and their Application to the Synthesis of Potential HIV Protease Inhibitors.
  • Mary Gower, Andrew Abell, IUPAC/ICOS-14 Conference, Christchurch . Synthesis of Inhibitors of Type II Dehydroquinase
  • Derek C. Martyn and Andrew D. Abell, IUPAC/ICOS-14 Conference, Christchurch , July 2002. Synthesis of Novel Pyrrole-Based Peptidomimetics as alpha-Chymotrypsin Inhibitors and Anti-Cancer Agents
  • Richard J. Payne, Alison D. Daines, Andrew D. Abell, Bruce Clark, IUPAC/ICOS-14 Conference, Christchurch , July 2002. Synthesis of Vitamin K Analogues and Protein Binding Studies for the Development of an Immunological Assay.
  • Shazaia Zaman, Mark Humphries and Andrew Abell, IUPAC/ICOS-14 Conference, Christchurch , July 2002. Synthesis of cyclic lactam protease inhibitors utilizing ring closing metathesis methodology
  • Christine Le Sann and Andrew Abell, IUPAC/ICOS-14 Conference, July 2002. The Design and Synthesis of Inhibitors of Type II Dehydroquinase
  • James Gardiner and Andrew Abell, IUPAC/ICOS-14 Conference, Christchurch , July 2002. The synthesis of conformationally restricted peptidomimetics using ring-closing metathesis.

 

  • Mark Humphries, Andrew Abell, IUPAC World Chemistry Conference in Brisbane , Australia , July 2001. 'Synthesis of Cyclic Lactam Protease Inhibitors Utilizising Ring Closing Metathesis Methodology'.
  • Andrew Abell, NZIC Conference, Napier, Dec 2001, ‘Peptidomimetics: Control of Chemical Shape and Reactivity'
  • Derek C Martyn, Brent K Nabbs, Barnaby CH May, Andrea J Vernall and Andrew D Abell, NZIC Conference, Napier, Dec 2001. Talk ‘Synthesis of novel pyrrole-based peptidomimetics and their chemical and biochemical applications'
  • Christine Le Sann and Andrew D. Abell, NZIC Conference, Napier, Dec 2001. Poster ‘The Design and Synthesis of Inhibitors of the Shikimate Pathway'
  • James Gardiner, Andrew D. Abell, NZIC Conference, Napier, Dec 2001. Poster ‘The Synthesis of Conformationally Restricted Peptidomimetics Using Ring Closing Metathesis'
  • Mary Gower, Kelly Smith, Andrew Abell, NZIC Conference, Napier, Dec 2001. Poster ‘Synthesis of type II Dehydroquinase Inhibitor' (poster prize).
  • Nathan Alexander, Andrew Abell, NZIC Conference, Napier, Dec 2001. Poster ‘Controlling the reactivity of enzyme inhibitors via molecular switches'
  • Anna R. McCarthy, Andrew D. Abell, Ian C. Shaw, NZIC Conference, Napier, Dec 2001. Poster ‘Structure-Activity Relationship Studies of Xenoestrogens and their Potential Activity as Endocrine Disruptors'
  • Richard J. Payne, Alison M. Daines, Andrew D. Abell, NZIC Conference, Napier, Dec 2001. Poster ‘Protein Binding Studies of Vitamin K Analogues for use in an Immunological Assay' (poster prise)
  • Mark E Humphries and Andrew D Abell, NZIC Conference, Napier, Dec 2001. ‘Synthesis of Functionalised Piperidinones'  
  • Derek Martyn, Andrew Abell, 37th National Organic Chemistry Symposium, June 10-14th 2001, Montana State University, Bozeman, Montana, USA. ‘An amino acid N-protecting group that can be coloured on demand.'
  • Mark Humphries, Andrew Abell, IUPAC World Chemistry Conference in Brisbane , Australia , July 2001. 'Synthesis of Cyclic Lactam Protease Inhibitors Utilizising Ring Closing Metathesis Methodology'.

 

  • Alison Daines and Andrew D. Abell. Royal Society of Chemistry Annual Conference, Mancester, April, 2000, UK.
  • Deryk Martyn and Andrew Abell. The 2000 International Chemical Congress of Pacific Basin Societies Pacifichem Lecture, Honolulu, Hawaii, USA, 14-19 Dec. 2000.
  • Andrew D. Abell, Barnaby C. H. May and Brent K. Nabbs. 26 th European Peptide Symposium, Montpellier , France , September 2000. ‘An Amino Acid Protecting Group that can be Colored on Demand'.
  • Andrew Abell, Brent K. Nabbs, Barnaby C. H. May. The 2000 International Chemical Congress of Pacific Basin Societies Pacifichem Lecture, Honolulu, Hawaii, USA, 14-19 Dec. 2000. ‘ The Chemistry and Biochemistry of Ring Deactivated Pyrroles.'
  • Andrew D. Abell , Applied Biosystems Workshop, 26 th European Peptide Symposium, Montpellier , France , September 2000.
  • Alison Daines and Andrew D. Abell. NZIC National convention, Wellington , October 1999. ‘Synthesis of Vitamin K Haptens.'
  • James Gardiner, Andrew D. Abell and Andrew J. Phillips: NZIC National convention, Wellington , October 1999. ‘Conformationally restricted peptidomimetics derived from phenylalanine'
  • Derek Martyn, Deborah Hoult and Andrew D. Abell: NZIC National convention, Wellington , October, 1999. ‘Stereocontrol of the Horner-Wadsworth Emmons Reaction and its application to the synthesis of HIV protease inhibitors'
  • Michael Edmonds and Andrew Abell, Molecular Modelling Conference Presentation, 1999, Brisbane
  • Michael Edmonds and Andrew Abell, Christchurch Medical School Lecture, June 1999. "Design and Synthesis of HIV Protease Inhibitors"
  • Andrew D. Abell, Two presentations at the 6 th National New Zealand Postgraduate Conference, Christchurch , November 1999.  
  • Michael Edmonds and Andrew Abell, FiRST Award for Postdoctoral Fellows Conference, Christchurch , June 1999.
  • Andrew D. Abell, Presentation at the Thirty-Fifth National Organic Symposium, University of Wisconsin-Madison , USA , June 1999.
  • ‘The photochemical regulation of serine protease activity'
  • Andrew D. Abell, Joint UOC/CHCH School of Medicine Health Symposium, Christchurch Medical School , June 1999
  • Andrew D. Abell, Invited Address at the 6th International Conference for AIDS, Cancer and Related Problems (St. Petersburg, Russia, May 1998). ‘Drug design and the synthesis of conformationally restricted HIV protease inhibitors'
  • Andrew D. Abell, Presentation at XVth EFMC International Synposium on Medicinal Chemistry (Sept 6-10th, 1998). ‘Photochemical regulation of serine protease activity'
  • M. Ratcliffe and Andrew D. Abell. Royal Australian Institute of Chemistry Organic Division conference, Leura, Sydney , July 1998. ‘Non-steroidal inhibitors of steroid 5alpha-reductase.'
  • Alison Daines and Andrew D. Abell. Royal Australian Institute of Chemistry Organic Division conference, Leura, Sydney , July 1998. ‘Analogues of vitamin K.'
  • James Gardiner and Andrew D. Abell. Royal Australian Institute of Chemistry Organic Division conference, Leura, Sydney , July 1998. ‘Conformationally restricted peptidomimetics.'
  • Michael Edmonds and Andrew Abell, Royal Australian Institute of Chemistry Organic Division conference, Leura, Sydney , July 1998. ‘Design and Synthesis of HIV Protease Inhibitors.'  
  • Andrew D. Abell, Presentation at the Thirty-Fifth National Organic Symposium, Trinity University, San Antonio, Texas, USA, June 1997. 'Reactions and properties of deactivated hydroxymethylpyrroles'  
  • Andrew D. Abell, New Zealand Institute of Chemistry (NZIC) Easterfield address at the NZIC National Convention, University of Otago , December 1996. Title of the address: 'The design of enzyme inhibitors based on enzyme-substrate interactions'
  • Andrew D. Abell, Invited address at the Australian National University Molecular Recognition Symposium, ANU, Canberra , Australia , April 1996. Title of the address: 'Enzyme inhibitors and pharmaceuticals based on enzyme-substrate interactions'
  • Andrew D. Abell, Invited presentation at the Symposium on Oceanian-Japanese Organic Chemistry Synthesis and Natural Products, Tokushima, Japan, December 1996. 'Synthesis and reactions of hydroxymethylpyrroles'
  • Andrew D. Abell, Address at the Brisbane Biological Chemistry Symposium 2, Griffith University , Queensland , Australia , June 1996. 'The synthesis and evaluation of non-steroidal inhibitors of steroid 5alpha-reductase'
  • Andrew D. Abell, Address at the Royal Australian Chemical Institute 15th National Organic Conference, Yeppoon , Queensland , Australia , June 1996. 'The design and synthesis of succinimide- and tetrazole-based peptidomimetic protease inhibitors'