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Stereochemistry of the side-chain dehydrogenation of N-benzyloxycarbonyl-(S)-tryptophan by Chromobacterium violaceum
Journal article

Stereochemistry of the side-chain dehydrogenation of N-benzyloxycarbonyl-(S)-tryptophan by Chromobacterium violaceum

Mark E Gustafson, Delwyn Miller, Patrick J Davis, John P Rosazza, Ching-Jer Chang and Heinz G Floss
Journal of the Chemical Society, Chemical Communications, Vol.1977(23), pp.842-843
1977
DOI: 10.1039/C39770000842

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Abstract

Using N-benzyloxycarbonyl-(2S,3R)- and -(2S, 3S)-[3-14C, 3-3H]tryptophan it was shown that the side-chain dehydrogenation of N-benzyloxycarbonyltryptophan by Chromobacterium violaceum involves a syn elimination of the hydrogens from C-2 and C-3 to give N-benzyloxycarbonyl-2,3-dehydrotryptophan of Z configuration.

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