Enantioselective lactate binding by chiral tripodal anion hosts derived from amino acids

被引：19

作者：

Barnard, Anna ^{[1
]}

Dickson, Sara Jane ^{[1
]}

Paterson, Martin J. ^{[2
]}

Todd, Adam M. ^{[1
]}

Steed, Jonathan W. ^{[1
]}

机构：

[1] Univ Durham, Dept Chem, Durham DH1 3LE, England

[2] Heriot Watt Univ, Sch Engn & Phys Sci, Edinburgh EH14 4AS, Midlothian, Scotland

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2009年 / 7卷 / 08期

基金：

英国工程与自然科学研究理事会;

关键词：

ELECTROSTATIC INTERACTIONS; RESTRICTED CONFORMATIONS; RECEPTORS; DESIGN; RECOGNITION; FLYTRAP; CATIONS; RUTHENIUM(II); CONSTRUCTION; LUMINESCENT;

D O I：

10.1039/b817889e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral, tripodal anion hosts derived from either S-phenylalanine or S-leucine bind D-lactate enantioselectively. The nature of the host-guest interaction has been probed by solution NMR methods and by DFT calculations. The calculations suggest that the D-lactate may form an additional hydrogen bond in the host-guest complex while the L-lactate complex contains an intramolecular hydrogen bond. Anion binding is in competition with host dimerisation, as demonstrated by DOSY and H-1 NMR spectroscopy, and DFT calculations.

引用

页码：1554 / 1561

页数：8

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