在一种人工精氨酸受体中，通过核磁共振检测胍盐质子与双膦酸盐部分之间的分子间NH…OP氢键。

NMR detection of intermolecular NH.OP hydrogen bonds between guanidinium protons and bisposphonate moieties in an artificial arginine receptor.

作者信息

Gschwind Ruth M, Armbrüster Marcia, Zubrzycki Igor Z

机构信息

Kekulé-Institut für Organische Chemie und Biochemie, Universität Bonn, Gerhard-Domagk-Str. 1, D-53121 Bonn, Germany.

出版信息

J Am Chem Soc. 2004 Aug 25;126(33):10228-9. doi: 10.1021/ja0483701.

DOI:10.1021/ja0483701

PMID:15315419

Abstract

Hydrogen bonding plays a major role in the selective recognition of guanidinium groups by receptor molecules. The present NMR investigation provides direct experimental evidence of hydrogen bonds in an artificial arginine receptor complex consisting of alpha-N-benzoylarginine ethyl ester and a bisphosphonate tweezers molecule. trans-Hydrogen bond 2hJHP couplings between the phosphonate moieties and individual guanidinium protons as well as the amide proton have been detected by [1H,31P]-HMBC and [31P,1H]-INEPT experiments. The detected hydrogen bonding network in the investigated artificial arginine receptor shows a symmetrical end-on interaction of the guanidinium moiety, which enables concerted rotations and deviates from the structure proposed for the biological arginine fork.

摘要

氢键在受体分子对胍基的选择性识别中起主要作用。目前的核磁共振研究为一种由α-N-苯甲酰精氨酸乙酯和双膦酸盐镊子分子组成的人工精氨酸受体复合物中的氢键提供了直接实验证据。通过[1H,31P]-HMBC和[31P,1H]-INEPT实验检测到了膦酸酯部分与单个胍基质子以及酰胺质子之间的反式氢键2hJHP耦合。在所研究的人工精氨酸受体中检测到的氢键网络显示出胍基部分的对称端对端相互作用，这使得协同旋转成为可能，并且与生物精氨酸叉所提出的结构有所不同。