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Issue 0, 1981

Biosynthesis of α-cyclopiazonic acid. Steric course of proton removal during the cyclisation of β-cyclopiazonic acid in Penicillium griseofulvum

Abstract

Feeding experiments with (3R)- and (3S)-[3-3H] tryptophan have shown that, in Penicillium griseofulvum Dierckx, incorporation of tryptophan into α-cycopiazonic acid (1) proceeds with loss of the 3-pro-S hydrogen atom. [3-2H2]Tryptophan was converted by P. griseofulvum into α-cyclopiazonic acid which was shown by 2H n.m.r. spectroscopy to contain deuterium only at the expected C-4 position. (2RS)-[2-3H,3-14C]Tryptophan was incorporated into α-cyclopiazonic acid (1) with loss of ca. 50% of the tritium. These findings are consistent with cyclisation of β-cyclopiazonic acid (4) to α-cyclopiazonic acid (1)via a 1,4-didehydro-derivative, with C–C bond formation at C-4 occurring from the side of the molecule opposite to that from which proton removal takes place.

Article information


J. Chem. Soc., Perkin Trans. 1, 1981, 3292-3294
Article type
Paper

Biosynthesis of α-cyclopiazonic acid. Steric course of proton removal during the cyclisation of β-cyclopiazonic acid in Penicillium griseofulvum

A. E. de Jesus, P. S. Steyn, R. Vleggaar, G. W. Kirby, M. J. Varley and N. P. Ferreira, J. Chem. Soc., Perkin Trans. 1, 1981, 3292 DOI: 10.1039/P19810003292

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