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Stereochemical course of tryptophan dehydrogenation during biosynthesis of the calcium-dependent lipopeptide antibiotics

B. Amir-Heidari, J. Thirlway, and Jason Micklefield

Organic Letters . 2007;9 :1513-1516.

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Abstract

Hydrogen atoms are abstracted from the C2??? and C3???-pro-S positions of an (S)-tryptophanyl precursor, with overall syn stereochemistry, during the biosynthesis of the C-terminal Z-2???,3???-dehydrotryptophan residue of the calcium-dependent lipopeptide antibiotics (CDAs) in Streptomyces coelicolor. The absence of ??-hydroxytryptophanyl, or other possible intermediates, further suggests a direct dehydrogenation mechanism similar to that proposed for the l-tryptophan 2???,3???-oxidase from Chromobacterium violaceum.

Bibliographic metadata

Type of resource:
Content type:
Publication type:
Published date:
Journal title:
Abbreviated journal title:
Volume:
9
Start page:
1513
End page:
1516
Total:
4
Pagination:
1513-1516
Digital Object Identifier:
10.1021/ol0701619
Access state:
Active

Institutional metadata

University researcher(s):

Record metadata

Manchester eScholar ID:
uk-ac-man-scw:17444
Created by:
Micklefield, Jason
Created:
25th September, 2009, 17:08:24
Last modified by:
Micklefield, Jason
Last modified:
16th October, 2009, 12:06:29

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