Biosynthetic Studies in Heterocyclic Fungal Metabolites

Pita Boente, Maria Isabel (1981) Biosynthetic Studies in Heterocyclic Fungal Metabolites. PhD thesis, University of Glasgow.

Abstract

The tryptophan analogues, beta-(2-azaindol-3-yl)-, beta-(7-azaindol-3-yl)- and beta-(l-benzothien-3-yl)-alanine, were synthesised and fed to PeniciIlium cyclopium cultures. The three compounds caused inhibition of normal fungal growth and metabolite production. 3-Acetyl-5-(indol-3-ylraethyl)-tetramic acid, a known intermediate in cyclopiazonic acid biosynthesis, labelled with 14C, was synthesised. After administration of this compound to cultures of P. cyclopium. no radioactivity was detected in the metabolites. It is presumed that cell-wall permeability problems were responsible for this result. When grown on a replacement medium containing no exogenous nitrogen source, P. cyclopium produced alpha- and beta-cyclopiazonic acids only when small amounts of 3-acetyl-5-(indol-3-yl- methyl)tetramic acid were added. However, when 3[2H3]acetyl-5-(indol-3-2 ylmethyl)-[5-2H]tetramic acid was administered, the alpha- and beta-cyclopiazonic acids isolated contained no deuterium. These results suggest that the tetramic acid is first degraded to tryptophan, which can then lose the 2 2H-atom in a transamination reaction, prior to incorporation into the metabolites.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Keywords: Organic chemistry, Biochemistry
• Date of Award: 1981
• Depositing User: Enlighten Team
• Unique ID: glathesis:1981-77159
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 14 Jan 2020 09:18
• Last Modified: 14 Jan 2020 09:18
• URI: https://theses.gla.ac.uk/id/eprint/77159