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Synthèse de la Ileu8-oxytocine et de la Val8-oxytocine, deux analogues de l'oxytocine modifiés dans la chaîne latérale

✍ Scribed by P.-A. Jaquenoud; R. A. Boissonnas

Publisher
John Wiley and Sons
Year
1961
Tongue
German
Weight
709 KB
Volume
44
Category
Article
ISSN
0018-019X

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✦ Synopsis

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.

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