Stereochemistry of the dehydrogenation of (2S)-histidine in the biosynthesis of roquefortine and oxaline

Abstract
A comparison of spectral data indicates the E configuration for the dehydrohistidine unit in both roquefortine and oxaline; incorporation of (2S,3S)- and (2S,3R)-[3-3H]histidine into roquefortine by Penicillium roqueforti and into oxaline by Penicillium oxalicum proceeded in each case with removal of the pro-S hydrogen atom from C(3).

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