Premium
Synthèse de la Ileu 8 ‐oxytocine et de la Val 8 ‐oxytocine, deux analogues de l'oxytocine modifiés dans la chaîne latérale
Author(s) -
Jaquenoud P.A.,
Boissonnas R. A.
Publication year - 1961
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.19610440116
Subject(s) - chemistry , liquid ammonia , azide , sodium azide , stereochemistry , medicinal chemistry , aqueous solution , ammonia , organic chemistry
N‐CBO‐L‐prolyl‐L‐isoleucyl‐glycine ethyl ester and N‐CBO‐L‐prolyl‐L‐valylglycine ethyl ester are synthesized by recurrent methods. Amidification of the ester group, splitting of the CBO group and condensation with N‐CBO‐L‐glutaminyl‐ L‐asparaginyl‐S‐benzyl‐L‐cysteinyl‐azide affords the two respective hexapeptides, which after splitting of the CBO group are condensed with N‐tosyl‐S‐benzyl‐L‐cysteinyl‐ L‐tyrosyl‐L‐isoleucyl‐azide. Cleavage of the protecting groups of the resulting two nonapeptides with sodium in liquid ammonia, oxydation with air in dilute aqueous solution and purification by counter‐current distribution, affords the desired cyclic nonapeptide amides : Ileu 8 ‐oxytocin and Val 8 ‐oxytocin. When tested on the cat uterus in situ the former is a stronger oxytocic than oxytocin itself.