Penicillin biosynthesis. On the stereochemistry of carbon–sulphur bond formation with modified substrates
- 1 January 1983
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 22,p. 1319-1320
- https://doi.org/10.1039/c39830001319
Abstract
Enzymatic conversion of the two modified substrates (S-α-amino-δ-adipyl)-S-cysteinyl-(2R,3R)-3-2H-α-aminobutyrate (2c) and (S-α-amino-δ-adipyl)-S-cysteinyl-(2R,3S)-3-2H-α-aminobutyrate (2d) by the enzyme isopenicillin N synthetase gave from both precursors the same penam product, namely (2S)-2-deuterio-norisopenicillin N, indicating that this enzyme is capable of forming carbon–sulphur bonds by retention and also inversion pathways respectively.Keywords
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