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- DOI: 10.1021/ol0701619
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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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Full-text held externally
- DOI: 10.1021/ol0701619
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.