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Abstract Detail

Secondary Metabolites

Newmister, Sean A. [1], Tran, Hong [1], Yu, Fengan [1], Li, Shengying [2], Berlinck, Roberto G. S. [3], Williams , Robert M. [4], Sherman, David H. [5].

Biosynthetic analysis of fungal derived [2.2.2] prenylated indole alkaloids.

Prenylated indole alkaloids are a diverse class of fungal secondary metabolites that demonstrate a range of biological activities including anticancer, antiparasitic, and antifungal properties. Considerable interest in the chemical synthesis and isolation of these metabolites has led to a wealth of tools to investigate the biosynthetic pathways that generate these diverse alkaloids. Recently, our laboratory has identified the biosynthetic gene clusters for the (+)/(‒)-notoamide, paraherquamide, malbrancheamide, waikialoid, and citrinalin alkaloids. Each of the clusters contains a bimodular non-ribosomal peptide synthetase accompanied by a series of prenyltransferases and oxidases, which complete the tailoring of the dipeptide core. Based on comparative analysis of these biosynthetic gene clusters, several enzymatic steps have been placed in a biosynthetic scheme that accounts for the structural differences observed within this panel of alkaloids. Many central steps in these pathways have been confirmed by heterologous expression, in vitro reconstitution, and gene disruption in the producing organism, providing key genetic and biochemical insights into the structural diversity of this important class of fungal alkaloids.

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1 - University of Michigan, Life Sciences Institute, 210 Washtenaw Ave., Ann Arbor, MI, 48109, USA
2 - Qingdao Institute of Bioenergy and Bioprocess Technology, 189 Songling Road, Laoshan District, Qingdao, 266101, China
3 - Universidade de São Paulo, Instituto de Química de São Carlos, Caixa Postal 780, CEP 13560-970, São Carlos, SP, Brasil
4 - Colorado State University, Department of Chemistry, Fort Collins, CO, 80523, USA
5 - University of Michigan, Departments of Chemistry, Microbiology & Immunology, and Life Sciences Institute, 210 Washtenaw Ave., Ann Arbor, MI, 48109, USA

secondary metabolites .

Presentation Type: Symposium or Colloquium Presentation
Session: SY3
Location: Room 104 AB/Kellogg Hotel and Conference Center
Date: Monday, June 9th, 2014
Time: 4:00 PM
Number: SY3003
Abstract ID:197
Candidate for Awards:None

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