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Study on the Molecular Recognition of α , α , α , β ‐ZnT( o ‐BocThr)APP toward Imidazole Derivatives and Amino Acid Esters
Author(s) -
Ruan WenJuan,
Zhao XiaoJing,
Wang ShuJun,
Zhang YingHui,
Zhang ZhiHuia,
Nan Jing,
Zhu ZhiAng,
Wang JianGuo,
Ma Yi
Publication year - 2005
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200591381
Subject(s) - chemistry , imidazole , molecular recognition , chloroform , circular dichroism , titration , chemical shift , stereochemistry , amino acid , quantum chemical , spectral line , molecule , crystallography , organic chemistry , biochemistry , physics , astronomy
Molecular Recognition of α , α , α , β ‐ZnT( o ‐BocThr)APP ( 1) toward a series of imidazole derivatives and amino acid esters was investigated. Association constants were determined in chloroform by means of UV‐Vis titration method. The association constants of 1 with imidazole derivatives are larger than those of 1 with amino acid esters. 1 H NMR spectra were investigated to describe the binding mode of the recognition system, showing that all the protons of the guests were shifted to upfield. The circular dichroism spectra of 1 ‐ L ‐/ D ‐ValOMe showed a split cotton effect in Soret region, while those of 1 ‐ L ‐/ D ‐PheOMe showed no split cotton effect. Molecular modeling was performed to understand chiral recognition on a molecular level. Quantum chemical calculation was carried out based on the stable conformations of these recognition systems, which gave a reasonable explanation for the behavior of molecular recognition. The results indicated that the conformation of 1 ‐ D ‐ValOMe was more stable than that of 1 ‐ L ‐ValOMe.