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

Citation
K. Umezawa et al., Biosynthesis of polyoxypeptin A: novel amino acid 3-hydroxy-3-methylproline derived from isoleucine, J CHEM S P1, (13), 2001, pp. 1550-1553
Citations number
7
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
1472-7781 → ACNP
Issue
13
Year of publication
2001
Pages
1550 - 1553
Database
ISI
SICI code
1472-7781(2001):13<1550:BOPANA>2.0.ZU;2-E
Abstract
Polyoxypeptin A is a hexadepsipeptide, isolated from Streptomyces, containi ng 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 der ived from isoleucine but not from proline. Isoleucine is also incorporated into the alkyl moiety of the C-15 acyl side chain, possibly through alpha - methylbutyryl-CoA. The piperazic acid moieties are synthesized from glutama te. Other hydroxylated amino acids are shown to be derived from each corres ponding amino acid.