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The biosynthesis of fungal metabolites derived from tryptophan

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thesis
posted on 2018-11-20, 17:23 authored by Michael J. Varley
The synthesis of 3-formylindole labelled in the formyl group with deuterium or tritium has been achieved via pyrolysis of the deuteriated or tritiated anilinium salt of indole-3-glyoxylic acid. The, labelled aldehydes have been used to prepare tryptophan stereoselectively labelled with deuterium or tritium in the β-methylene group by the oxazolinone method. The configurations of the labelled tryptophans were established by 1H n.m.r. spectroscopy of the deuteriated compounds and by chemical and enzymic degradation of the tritiated compounds to fumaric acid via 4,7-dihydrotryptophan and aspartic and malic acids. In addition, biosynthetic conversion of the tritiated compounds into the antibiotic indolmycin has confirmed the assignments of configuration and established stereochemical purities of ca. 94%. [Continues.]

Funding

Science Research Council (research studentship).

History

School

  • Science

Department

  • Chemistry

Publisher

© Michael John Varley

Publisher statement

This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/

Publication date

1975

Notes

A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of the degree of Doctor of Philosophy at Loughborough University.

Language

  • en

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