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- DOI: 10.1021/jo701660v
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NMR confirmation that tryptophan dehydrogenation occurs with syn-stereochemistry during the biosynthesis of CDA in Streptomyces coelicolor.
B. A. Heidari and J. Micklefield
Journal of Organic Chemistry. 2007;72:8950-8953.
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Full-text held externally
- DOI: 10.1021/jo701660v
Abstract
Doubly labeled (2‘S,3‘R)-[3‘-2H1,13C1]-tryptophan was fed to the Trp-His auxotrophic Streptomyces coelicolor strain WH101. Mass spectrometry showed single and double incorporation of the labeled Trp into the calcium-dependent lipopeptide antibiotic (CDA4a). From 13C NMR spectroscopy, it was apparent that the C3‘-signal of the (Z)-2‘,3‘-dehydrotryptophan (position 11 in CDA4) was a 1:1:1 triplet indicating that the deuterium atom in the pro-R position of the methylene group is retained during Trp-oxidation. This provides definitive proof that Trp dehydrogenation occurs through the loss of the 2‘ and pro-3‘S hydrogen atoms with overall syn stereochemistry.