Rich Taylor

Rich Taylor

Synthetic Organic Chemistry Conformation-Activity Relationships of Polyketide Natural Products

Biography

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2014-present
Interim Director of the Warren Family Research Center for Drug Discovery and Development, University of Notre Dame
2013-2016
Associate Vice President for Research, University of Notre Dame
2008-2013
Associate Dean, College of Science, University of Notre Dame
2004-present
Professor, University of Notre Dame
2001-2004
Associate Professor, University of Notre Dame
1995-2001
Assistant Professor, University of Notre Dame
1992-1995
Merck Postdoctoral Associate, Stanford University
1992
Ph.D. in Chemistry, Rensselaer Polytechnic Institute
1987
B.S. in Chemistry, State University of New York, Oswego

Selected Awards

2009
Elected Fellow, American Association for the Advancement of Science
2007
Rev. Edmund P. Joyce Award for Excellence in Undergraduate Teaching
2007
Silveira Distinguished Lecturer, SUNY, Oswego
2002
Kaneb Teaching Award
2000
Eli Lilly Grantee Award
1998
NSF CAREER Award

Research Interests

Our group is interested in the exploring the potential of polyketide natural products as chemotherapeutic agents particularly directed against cancer. Towards this end our group's expertise includes synthetic chemistry, molecular modeling, and molecular biology/biochemistry. In recent years the we have completed the total synthesis of the complex natural products, epothilones A, B, C and D, myriaporones 1, 3 and 4, peloruside A, neopeltolide, tolypothrix polyethers, and gephyronic acid.

Our analogue design strategy is focused towards the determination of the structural and conformational constraints of binding. Our group has demonstrated that the information gained from what we have termed conformation-activity relationships complements classic SAR with the goal of providing a detailed pharmacophore model and assist in the design of future chemotherapeutic agents.  In addition to our successful total syntheses and medicinal chemistry efforts, our group has already contributed significantly to the field of organic synthesis through the development of a number of new synthetic methodologies that solved key problems in our targeted efforts.

Another unique aspect of our analogue design strategy is the exploitation of biosynthetic enzymes called polyketide synthases. We are actively pursuing the isolation and characterization of polyketide synthase gene clusters responsible for the production of biologically active natural products. We have demonstrated the semi-synthetic production of epothilone natural products and analogues through the use of genetically engineered organisms thus alleviating any concerns about the high cost of total synthesis of compounds of this complexity.

Synthetic Methodology and Total Synthesis

Conformation-Activity Relationships

Polyketide Synthases and Biosynthesis

 

Recent Papers

  • Wagner, D.T.; Stevens, D.C.; Mehaffey, M.R.; Manion, H.R.; Taylor, R.E.; Brodbelt, J.S.; Keatinge-Clay, A.T. "alpha-Methylation follows condensation in the gephyronic acid modular polyketide synthase." Chem. Commun. 2016, 52(57), 8822-8825.
  • Chang, C.F.; Stefan, E.; Taylor, R.E. "Total Synthesis and Structural Reassignment of Lyngbyaloside C Highlighted by Intermolecular Ketene Esterification." Chem. Eur. J. 2016, 21(30), 10681-10686.
  • Stefan, E.; Taylor, R.E. "1,5-Hydride Transfer Protocol for the Synthesis of beta-Branched Polyketide Structural Units." Tetrahedron Lett. 2015, 56 (23), 3416-3419.
  • Naini, A.; Muthukumar, Y.; Raja, A.; Franke, R.; Harrier, I.; Smith, A.B.; Lee, D.; Taylor, R.E.; Sasse, F.; Kalesse, M. "The Synthesis and Biological Evaluation of Desepoxyisotedanolide and a Comparison with Desepoxytedanolide." Angew. Chem. Int. Ed. 2015, 54(23), 6935-6939.
  • Larsen, E.M.; Wilson, M.R.; Taylor, R.E. "Conformation-activity relationships of polyketide natural products." Nat. Prod. Rep. 2015, 32(8), 1183-1206.
  • Young, J.; Stevens, D.C.; Carmichael, R.; Tan, J.; Rachid, S.; Boddy, C.N.; Muller, R.; Taylor, R.E. "Elucidation of Gephyronic Acid Biosynthetic Pathway Revealed Unexpected SAM-Dependent Methylations." J. Nat. Prod. 2013, 76(12), 2269-2276.

        Full publication list:  Link

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