Rhodes University Logo

Professor Perry T. Kaye

BSc (Natal), BSc (Hons) (UNISA), MSc (Natal), DPhil (Oxon), FRSC, FRSSAf.
Professor of Organic Chemistry, Rhodes University (1987-2007). (1987-2007)  
Head of the Department of Chemistry (1991-2007), Rhodes University.
Director, Rhodes Centre for Chemico- and Biomedicinal Research (2005- )
Professor Emeritus (2008- )


RESEARCH INTERESTS.

1.  Synthetic Methodology.
Applications of the Baylis-Hillman reaction in the synthesis of benzanulated heterocyclic systems and their elaboration to biologically active compounds.
2. Medicinal Chemistry.
Design, synthesis and in silico and in vitro evaluation of the medicinal potential of novel compounds as anti-parasitic (anti-malarial and anti-trypanosomal), HIV-1 PR, IN and RT inhibitors and anti-TB agents.
2.  Physical Organic Chemistry
Kinetic-mechanistic studies of organic reaction mechanisms using spectroscopic and computational methods.


AWARDS AND SELECTED LECTURES

•    Vice Chancellor's Distinguished Teaching Award/Medal, Rhodes University, 1994.
•    AECI Medal of the South African Chemical Institute, 1996
•    Vice Chancellor's Distinguished Senior Research Award/Medal, Rhodes University, 2001.
•    Gold Medal of the South African Chemical Institute, 2007.

•    Of Molecules and Men, Inaugural Lecture, Rhodes University, 1989.
•    Dimensions of Reality - a Chemist's Perspective, University Lecture as recipient of 1994 Vice-Chancellor's Distinguished Teaching Award, 1995.
•    Through the Looking Glass - Reflections on the Chemical Implications of Chirality, Joint meeting of the South African Chemical Institute (SACI) - East Cape Division and the Royal Society of South Africa; as 1996 recipient of the AECI Medal (SACI), 1997.
•    Senecio Alkaloids, Serendipity and Synthesis - the Warren Connection, Frank Warren Lecture at the 1997 Frank Warren National Organic Chemistry Conference, Mtunzini.
•    Through the Looking Glass - Confronting Chirality in Synthesis, Plenary Lecture at Interscience '98, University of the North, Pietersburg, Oct., 1998.
•    The Baylis-Hillman Zwitterion - Reactivity and Substrate Selectivity, Invited Lecture presented at the International Workshop on Reactive Intermediates-1999 (IWRI -99), Szczyrk, Poland, Aug., 1999.
•    The Baylis-Hillman Zwitterion - Reactivity and Substrate Selectivity, Lecture presented, by invitation, in the Department of Chemistry, University of York, UK, September, 1999.
•    The Baylis-Hillman Zwitterion - Reactivity and Substrate Selectivity, Lecture presented, by invitation, in the Department of Chemistry, Imperial College, October, 1999.
•    The Baylis-Hillman Entrée to Heterocyclic Systems, Invited Keynote Lecture presented at the RSC/SACI 1st International Conference: Organic Chemistry, University of Cape Town, Jan., 2001.
•    Camphor-derived Chiral Auxiliaries in Asymmetric Synthesis, Invited Lecture, presented at the University of York, UK, Sept., 2003.
•    Design, Synthesis and Evaluation of Novel Metal-Selective Ligand Systems, Lecture presented at the University of St Andrews, UK, Sept., 2003.
•    Through the Looking Glass - Confronting Chirality in Synthesis, The Royal Society of Chemistry Frank Warren Memorial Lecture, presented at the University of Cape Town, Oct., 2003.
•    Medicinal Chemistry Research – a South African Perspective, ICS-UNIDO Expert Group Meeting, Trieste, Italy, Oct., 2004.
•    Through the Looking Glass –a stereochemical adventure The Victor Pretorius Memorial Lectures, University of Pretoria, May, 2006.
•    Mechanisms: Making Sense of Complexity, P.T. Kaye, the 2007 SACI Gold Medal Lecture presented at BOCC’08 – Bi-national Organic Chemistry Conference, Kruger National Park, Sept. 2008.
•    Medicinal Chemistry Challenges in Africa – an Academic Response, P.T. Kaye, Lecture presented at iThemba Pharmaceuticals Launch, Johannesburg, March., 2009.
•    25 Years of Organic Chemistry @ Rhodes, Invited Lecture, SACI Centenary Symposium, East London, 2012.
•    Journeys in Molecular Space: Experimental and Theoretical Studies of Baylis-Hillman-Mediated Transformations, Invited Plenary Lecture, SACI National Convention, East London, Dec., 2013
•    Baylis-Hillman Mediated Benzannulation Strategies: Experimental and Theoretical Studies Invited Lecture at the SACI-ACS Binational Organic Chemistry Conference, Stellenbosch, Dec., 2014.

SABBATICAL VISITS
1. University of Cambridge, July 1985? January 1986; project arranged jointly with Professor Jack Lewis and Dr. Olga Kennard on X?ray crystallography and oligonucleotide synthesis.
2. University of Cambridge, April? September, 1990; worked with Dr. D.H. Williams on antibiotic ligand binding.
3. University of York, July - September, 1999: worked with Prof. R.E. Hubbard on the application of computer modelling to biologically significant molecules.
4. University of Oxford, June – September, 2003; worked with Prof. W.G. Richards’ group, applying ab initio and DFT calculations to organic reaction mechanisms.

SUMMARY OF RESEARCH OUTPUT and RECENT PUBLICATIONS
166      Papers published or in press in peer-reviewed journals (as at March, 2017)
71       Higher degrees (MSc and PhD) supervised/co-supervised and successfully completed

•    Strong Base- or Acid-mediated Chemoselectivity Shifts in the Synthesis of 2H-Chromene or Coumarin Derivatives from Common Baylis-Hillman Adducts.Faridoon, Temitope  O. Olomola, Matshawandile Tukulula, Rosalyn Klein and Perry T. Kaye
Tetrahedron, 2015, 71, 4868-4873.
•    Synthesis and Evaluation of 3-Hydroxy-3-phenylpropanoate Ester-AZT Conjugates as Potential Dual-action HIV-1 Integrase and Reverse Transcriptase Inhibitors
M.H. Manyeruke, T.O. Olomola, S. Majumder, S. Abrahams, M. Isaacs, N. Mautsa, S. Mosebi, D. Mnkandhla, R. Hewer, H.C. Hoppe, R. Klein and P.T. Kaye
Bioorg. & Med. Chem., 2015, 24, 7521-7528.
•    Application of Baylis-Hillman Methodology in the Direct Construction of Chromone Derivatives
Faridoon, Temitope.O. Olomola, Rosalyn Klein and Perry.T. Kaye*
Tetrahedron, 2016, 72, 392-395.
•    Elucidating Latent Mechanistic Complexity in Competing Acid-Catalysed Reactions of Salicylaldehyde-derived Baylis-Hillman Adducts
          Temitope  O. Olomola, Rosalyn Klein, Mino R. Caira and Perry T. Kaye *
          J. Org. Chem., 2016, 81 (1), 109–120.
•    Synthesis and Antimalarial Activity of N-Benzylated (N-Arylcarbamoyl)alkylphosphonic Acid Derivatives
C.M. Adeyemi, Faridoon, M. Isaacs,  D. Mnkandhla, H.C. Hoppe, R.W.M.Krause and P.T. Kaye*
Bioorg. & Med. Chem., 2016, 24, 6131-6138.
•    Synthesis and Evaluation of Substituted 4-(N-Benzylamino)cinnamate Esters as Potential Anti-Cancer Agents and HIV-1 Integrase Inhibitors
Faridoon, Adrienne L. Edkins, Michelle Isaacs, Dumisani Mnkandhla, Heinrich C. Hoppe, and Perry T. Kaye*
Bioorg. & Med. Chem. Lett., 2016, 26, 3810-3812.
•    Synthesis of novel camphor-derived chiral auxiliaries and their application in asymmetric Morita-Baylis-Hillman reactions
Lulama P. Mciteka, Kevin A. Lobb and Perry T. Kaye
Arkivoc, 2016 (v) 151-163.
•    Regioselective Synthesis and Anti-parasitic Activity of C-Benzylated (N-arylcarbamoyl)alkylphosphon-ate Esters
Christiana M. Adeyemi, Rosalyn Klein, Michelle Isaacs, Dumisani Mnkandhla, Heinrich C. Hoppe, Rui W.M. Krause and Perry T. Kaye.
Tetrahedron, 2017, 73, 1661-1667.
•    Synthesis and Biological Evaluation of (E)-Cinnamic Acid, (E)-2-Styrylthiazole and (E)-2-[2-(Naphthalen-1-yl)vinyl)] Derivatives
Emmanuel O. Olawode,* Roman Tandlich, Earl Prinsloo, Michelle Isaacs, Heinrich Hoppe, Ronnett Seldon, Digby F. Warner, Vanessa Steenkamp and
Perry T. Kayec*
Arkivoc, in press

Contact Information:
Telephone: +27 46 603 8268
Fax: +27 46 622 5109
Secretary: +27 46 603 8254

Postal Address:     Department of Chemistry
             Chemical and Pharmaceutical Sciences Building
             Corner of University and Artillery Roads
             Grahamstown
             6140
Courier Address:    Room F39
             Department of Chemistry
             Cnr. of University and Artillery Roads
             Rhodes University
             Grahamstown
             6140
             South Africa

Last Modified :Wed, 29 Mar 2017 12:41:21 SAST