质子核磁共振研究青霉胺残基对阿片受体选择性生长抑素衍生物二硫键环系统的构象影响。

Proton n.m.r. investigation of conformational influence of penicillamine residues on the disulfide ring system of opioid receptor selective somatostatin derivatives.

作者信息

Sugg E E, Tourwe D, Kazmierski W, Hruby V J, Van Binst G

机构信息

Department of Chemistry, University of Arizona, Tucson.

出版信息

Int J Pept Protein Res. 1988 Feb;31(2):192-200. doi: 10.1111/j.1399-3011.1988.tb00022.x.

DOI:10.1111/j.1399-3011.1988.tb00022.x

PMID:2896639

Abstract

Three cyclic disulfide analogs related to somatostatin, D-Phe(1)-cyclo(Cys(2)-Tyr(3)-D-Trp(4)-Lys(5)-Thr(6)-Xxx(7))-Thr(8)- NH2 (where Xxx = L-Pen 1; L-Cys 3; or D-Pen 4) were examined in DMSO-d6 by one- and two-dimensional proton n.m.r. spectroscopy in order to analyze the conformational influence of the position-7 residue on the 20-membered disulfide ring. From these studies it was concluded that all three analogs maintain a beta II' turn solution conformation for the core tetrapeptide -Tyr(3)-D-Trp(4)-Lys(5)-Thr(6)-. However, the disulfide conformation differs in the analogs, with 1 and 3 having a left-handed and 4 a right-handed disulfide chirality.

摘要

为了分析7位残基对20元二硫环的构象影响，通过一维和二维质子核磁共振光谱在氘代二甲亚砜中研究了三种与生长抑素相关的环状二硫类似物，即D-Phe(1)-环(Cys(2)-Tyr(3)-D-Trp(4)-Lys(5)-Thr(6)-Xxx(7))-Thr(8)-NH2（其中Xxx = L-Pen 1；L-Cys 3；或D-Pen 4）。从这些研究得出结论，所有三种类似物的核心四肽-Tyr(3)-D-Trp(4)-Lys(5)-Thr(6)-均保持βII'转角溶液构象。然而，类似物中的二硫构象不同，1和3具有左手二硫手性，4具有右手二硫手性。