Title:        Biosynthesis of Loline Alkaloids.

Reporter: Prof. Robert B. Grossman

                  Department of Chemistry, University of Kentucky  

Time:        3:00-4:00

Date:         May 28^th, 2015

Venue:      A408 Tang Ao-Qing Building (唐敖庆楼A区408)

Abstract:

                  The loline alkaloids are a group of insecticidal alkaloids produced by endophytic fungi living inside of cool-season grasses. These small secondary metabolites consist of a pyrrolizidine ring bearing an amino group and a strained ether bridge in a very unusual context for a biological product. We have identified and sequenced the gene cluster that encodes the enzymes responsible for synthesizing the loline alkaloids, and, with a combination of various chemical and molecular biological techniques, we have established the biochemical pathway that fungi use to prepare lolines, and we have mostly identified which enzymes are responsible for catalyzing which steps in the biosynthesis. Among our more unusual findings is that a PLP-dependent gamma-lyase, LolC, probably catalyzes the formation of a C–N bond in the first committed step of loline biosynthesis, and that a single non-heme iron-dependent oxidase, LolO, is responsible for introducing both C–O bonds of the ether bridge in a four-electron oxidation.

Bio Information:

                   Robert B. Grossman is a Professor of Chemistry at the University of Kentucky. He is the author of about 50 peer-reviewed papers in the areas of synthetic methods development, natural product synthesis, and chemical ecology. He is also the author of The Art of Writing Reasonable Organic Reaction Mechanisms, an intermediate-level textbook used around the world. He is also the cocreator of ACE Organic, a Web-based program for teaching organic chemistry whose functionality is now available in Pearson’s Mastering Chemistry program. Dr. Grossman was recently elected to the University of Kentucky Board of Trustees by his fellow faculty members. 

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