Synthèse de la Ileu 8 ‐oxytocine et de la Val 8 ‐oxytocine, deux analogues de l'oxytocine modifiés dans la chaîne latérale
1961; Wiley; Volume: 44; Issue: 1 Linguagem: Inglês
10.1002/hlca.19610440116
ISSN1522-2675
AutoresP Jaquenoud, R. A. Boissonnas,
Tópico(s)Molecular Spectroscopy and Structure
ResumoN‐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.
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