Une nouvelle synthèse de l'oxytocine

A new synthesis of oxytocin is described, where the CBO group is removed by HBr in acetic acid and the hexapeptide is condensed with N-CBO-S-benzyl-L-cysteinyl- L-tyrosyl- l-isoleucyl-azide to give the nonapeptides.

Abstract

Abstract A new synthesis of oxytocin is described. N‐CBO‐ L ‐glutaminyl‐ L ‐asparaginyl‐S‐benzyl‐ L ‐cysteinyl‐azide is reacted with L ‐prolyl‐ L ‐leucyl‐glycinamide to give N‐CBO‐ L ‐ glutaminyl‐ L ‐asparaginyl‐S‐benzyl‐ L ‐cysteinyl‐ L ‐prolyl‐ L ‐leucyl‐glycinamide. After removal of the CBO group by HBr in acetic acid this hexapeptide is condensed with N‐CBO‐S‐benzyl‐ L ‐cysteinyl‐ L ‐tyrosyl‐ L ‐isoleucyl‐azide to give the nonapeptide N‐CBO‐S‐benzyl‐ L ‐cysteinyl‐ L ‐tyrosyl‐ L ‐ isoleucyl‐ L ‐glutaminyl‐ L ‐asparaginyl‐S‐benzyl‐ L ‐cysteinyl‐ L ‐prolyl‐ L ‐leucyl‐glycinamide already obtained by du Vigneaud and coworkers through another route. Reduction with sodium in liquid ammonia and reoxydation gives biologically active material.