THE SYNTHESIS OF ARYL SUBSTITUTED ANALOGS OF PHENOXYACETYL-L-CYSTEINYL-D-VALINE AND PHENYLACETYL-L-CYSTEINYL-D-VALINE - APPLICATION TO THE PHOTOAFFINITY-LABELING OF ISOPENICILLIN N SYNTHETASE
- The acetylaryldipeptides (4a) - (4b) have been synthesised In high yield, and found to be converted to the corresponding penicillins (5a) -(5d) by Isopenicillin N Synthetase (IPNS). Of these, the m-substituted analogue (4c) was converted most efficiently. The synthesis of a potential photoaffinity label for IPNS which Incorporates this molecular framework, 2-[3-(3-trifluoromethyl-3H-diazirin-3-yl)phenoxy]acetyl-S-carbomethoxysulfenyl-L-cysteinyl-D-valine (21), is described. © 1987.
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