Issue 13, 2001

Biosynthesis of polyoxypeptin A: novel amino acid 3-hydroxy-3-methylproline derived from isoleucine

Abstract

Polyoxypeptin A is a hexadepsipeptide, isolated from Streptomyces, containing the novel amino acid (2S,3R)-3-hydroxy-3-methylproline. Its biosynthetic pathway is studied by incorporation of stable isotope-labelled amino acids and carboxylic acids. (2S,3R)-3-Hydroxy-3-methylproline is shown to be derived from isoleucine but not from proline. Isoleucine is also incorporated into the alkyl moiety of the C15 acyl side chain, possibly through α-methylbutyryl-CoA. The piperazic acid moieties are synthesized from glutamate. Other hydroxylated amino acids are shown to be derived from each corresponding amino acid.

Graphical abstract: Biosynthesis of polyoxypeptin A: novel amino acid 3-hydroxy-3-methylproline derived from isoleucine

Article information

Article type
Paper
Submitted
01 Mar 2001
Accepted
16 May 2001
First published
15 Jun 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 1550-1553

Biosynthesis of polyoxypeptin A: novel amino acid 3-hydroxy-3-methylproline derived from isoleucine

K. Umezawa, Y. Ikeda, O. Kawase, H. Naganawa and S. Kondo, J. Chem. Soc., Perkin Trans. 1, 2001, 1550 DOI: 10.1039/B101942M

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