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Transformation of alfa-Hydroxymethylamino Acids into alfa--Mercaptomethylamino Acids (alfa-Alkylcysteines)*[1]

Olma A.

Polish Journal of Chemistry

2004

Vol. 78 / nr 6

831-835

N-Boc-_-alkylserines (_-hydroxymethylamino acids) undergo a cyclization reaction without racemization to N-Boc-_-alkylserine-_-lactones in 90-98% yield using Mitsunobu conditions (Ph P, diethyl azodicarboxylate). Treatment of the corresponding _-lactones with sulphur nucleophiles (thiolacetic acid or 4-methoxybenzylmercaptan) gives S-protected N-Boc-_-alkylcysteines (_-mercaptomethylamino acids) in high yield. These chimeric _,_-disubstituted amino acids, being incorporated into peptide chain, are able to close the cyclic structure as a disulfide bond.