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Synthesis of fragments of arginine vasopressin and oxytocin containing a cystine residue in position 6

1984; Royal Netherlands Chemical Society; Volume: 103; Issue: 2 Linguagem: Inglês

10.1002/recl.19841030205

1878-7096

J. W. VAN NISPEN, J. A. J. Hannink, M. S. Schoffelmeer, W. P. A. Janssen, J. P. Polderdijk, H. M. Greven,

Neuroscience of respiration and sleep

Abstract The synthesis is described of several fragments of the neurohypophyseal nonapeptide hormones arginine vasopressin and oxytocin. One group of fragments is characterized by the presence of an asymmetrical disulfide (a cystine residue in position 6), a second group consists of dimeric (symmetrical disulfides) fragments. As common intermediates, peptides containing an S ‐tritylcysteine residue were synthesized by the fragment condensation approach. Treatment with methoxycarbonylsulfenyl chloride followed by reaction with the free thiol function of cysteine gave the asymmetrical disulfides, while treatment of the S ‐tritylcysteine containing peptide with iodine resulted in the corresponding dimers. Peptides with an N ‐terminal glutamine residue (position 4) were found to convert spontaneously into the corresponding pyroglutamic acid products.