Premium
Synthèse de la Lys 8 ‐oxytocine (lysine‐vasotocine) et nouvelle synthèse de la lysine‐vasopressine
Author(s) -
Boissonnas R. A.,
Huguenin R. L.
Publication year - 1960
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.19600430126
Subject(s) - chemistry , liquid ammonia , lysine , azide , aqueous solution , stereochemistry , oxytocin , medicinal chemistry , ammonia , organic chemistry , amino acid , biochemistry , medicine
N‐CBO‐ L ‐Glutaminyl‐ L ‐asparaginyl‐S‐benzyl‐ L ‐cysteinyl‐azide has been condensed with L‐prolyl‐ϵ‐N‐tosyl‐ L ‐lysyl‐glycinamide, giving N‐CBO‐ L ‐glutaminyl L‐asparaginyl‐S‐benzyl‐ L ‐cysteinyl‐ L ‐prolylϵ‐N‐tosyl‐ L ‐lysyl‐glycinamide, which after spliting of the CBO‐protecting group has been condensed with N‐CBO‐S‐benzyl‐ L ‐cysteinyl‐ L ‐tyrosyl‐ L ‐isoleucyl‐azide. Cleavage of the protecting groups of the resulting nonapeptide with sodium in liquid ammonia, oxidation with air in dilute aqueous solution and purification by counter‐current distribution afforded Lys 8 ‐oxytocin, which represents a structural intermediate between oxytocin and lysine‐vasopressin and which exhibits the biological properties of both these natural hormones.