用酰胺基团取代催产素中的二硫键。（环-（1-L-天冬氨酸，6-L-α，β-二氨基丙酸））催产素的合成及某些生物学性质。

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.

作者信息

Smith C W, Walter R, Moore S, Makofske R C, Meienhofer J

出版信息

J Med Chem. 1978 Jan;21(1):117-20. doi: 10.1021/jm00199a023.

PMID:619141

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, has been undertaken. The protected nonapeptide was prepared in a stepwise manner by solution techniques; after removal of side-chain protecting groups, formation of the briding 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.

摘要

作为对神经垂体激素中二硫键的空间和电子功能对其生物活性影响的持续研究的一部分，已开展了“催产素内酰胺”，即[环 -（1 - 天冬氨酸，6 - α，β - 二氨基丙酸）]催产素的合成。通过溶液技术逐步制备了受保护的九肽；去除侧链保护基团后，通过氧化还原缩合形成桥连酰胺键。该类似物对大鼠子宫的兴奋作用、对禽类血管的降压作用以及对大鼠的抗利尿作用的效价分别为16±2、6.6±0.6和5.6±3.8单位/毫克。