Publication | Closed Access
Stereospecificity of β-lactam formation in penicillin biosynthesis
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1986
Year
BiosynthesisAntibioticsBiochemistryPenicillin BiosynthesisBiocatalysisIsopenicillin NBacteriologyComplete LossComplete RetentionNatural SciencesNatural Product BiosynthesisPeptide SynthesisMicrobiologyMedicineAntimicrobial ResistanceBiomolecular EngineeringNatural Product Synthesis
The conversion of the tripeptide δ-L-α-aminoadipolyl-L-cysteinyl-D-valine into isopenicillin N catalysed by the enzyme isopenicillin N synthetase has been shown to occur with complete retention of the cysteinyl 3-pro-R-hydrogen and with complete loss of the cysteinyl 3-pro-S-hydrogen [δ-L-α-aminoadipoyl = 5-(5S)-amino-5-carboxypentanoyl].