Premium
Une nouvelle synthèse de l'oxytocine
Author(s) -
Boissonnas R. A.,
Guttmann St.,
Jaquenoud P.A.,
Waller J.P.,
Cherbuliez E.,
Stoll A.
Publication year - 1955
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19550380622
Subject(s) - chemistry , sodium azide , stereochemistry , azide , liquid ammonia , acetic acid , medicinal chemistry , ammonia , organic chemistry
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.