Replacement of the disulfide bond in oxytocin by an amide group. Synthesis and some biological properties of [cyclo-(1-L-aspartic acid, 6-L-.alpha.,.beta.-diaminopropionic acid)]oxytocin
- 1 January 1978
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 21 (1), 117-120
- https://doi.org/10.1021/jm00199a023
Abstract
As part of a continuing investigation of the steric and electronic functions of the disulfide group in neurohypophyseal hormones on their biological activity, the synthesis of oxytocin lactam, [cyclo-(1-aspartic acid,6-.alpha.,.beta.-diaminopropionic acid)]oxytocin, was undertaken. The protected nonapeptide was prepared in a stepwise manner by solution techniques; after removal of side-chain protecting groups, formation of the bridging amide bonds was accomplished by oxidation-reduction condensation. The analogue possesses rat uterotonic, avian vasodepressor and rat antidiuretic potencies of 16 .+-. 2, 6.6 .+-. 0.6 and 5.6 .+-. 3.8 units/mg, respectively.Keywords
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