A New Synthesis of Oxytocin Using S‐Carbobenzoxy‐Cysteines and N‐p‐Methoxybenzyloxycarbonyl‐Amino Acids as Intermediates
- 1 January 1969
- journal article
- research article
- Published by Wiley in Bulletin des Sociétés Chimiques Belges
- Vol. 78 (7-8) , 395-405
- https://doi.org/10.1002/bscb.19690780708
Abstract
A new synthesis of oxytocin is described. For the protection of the α‐amino functions the p‐methoxybenzyloxycarbonyl‐group was used. The phenolic hydroxyl of tyrosine was protected by the usual benzyl group. The free thiol functions of the cysteine moieties were protected by the carbobenzoxy group. For building up the peptide chain the step wise p‐nitrophenylester method was used. At the end of the synthesis, a fully protected nonapeptide amide was obtained, namely S–Z–N–pMZ–L–Cys–L–Tyr–L–lle–L–Glu(NH2)–L–Asp(NH2)–S–Z–L–Cys–L–Pro–L–Leu–Gly(NH2).All the protecting groups from this protected nonapeptide‐amide were removed by a reduction with sodium in liquid ammonia. After oxydation by aeration, oxytocin was obtained in a good yield.Keywords
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