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Stereochemistry of the incorporation of valine methyl groups into methylene groups in cephalosporin C.


ABSTRACT: 'Chiral methyl valines', i.e. samples of valine labelled stereospecifically in the methyl groups with 2H and 3H, were incorporated into cephalosporin C by a suspension of washed cells of Cephalosporium acremonium. Analysis by 3H n.m.r. of the cephalosporin C produced showed that the conversion of the 3-pro-S-methyl group of valine into the acetoxymethyl side-chain was a highly stereospecific process. By contrast, conversion of the 3-pro-R-methyl group into the endocyclic methylene group of the dihydrothiazine ring was shown to proceed by a non-stereospecific process.

SUBMITTER: Pang CP 

PROVIDER: S-EPMC1144242 | biostudies-other | 1984 Sep

REPOSITORIES: biostudies-other

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