Solvent effects in carbohydrate binding by synthetic receptors: Implications for the role of water in natural carbohydrate recognition

被引：75

作者：

Klein, Emmanuel ^{[1
]}

Ferrand, Yann ^{[1
]}

Barwell, Nicholas P. ^{[1
]}

Davis, Anthony P. ^{[1
]}

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 14期

基金：

英国工程与自然科学研究理事会;

关键词：

carbohydrates; hydrogen bonds; hydrophobic effect; molecular recognition; solvent effects;

D O I：

10.1002/anie.200704733

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) How do they do it? Carbohydrates are intrinsically difficult to bind in water. Lectins and other proteins succeed, but do they use polar or hydrophobic interactions? Studies of synthetic lectins in mixed solvent systems shed new light onto this contentious issue (see scheme; X=hydrophobic or hydrophilic solubilizing groups; R=H or alkyl group). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：2693 / 2696

页数：4

共 50 条

[1] Synthetic molecular cage receptors for carbohydrate recognition
Wu, Baoqi
Tang, Rongzhi
Tan, Yu
NATURE REVIEWS CHEMISTRY, 2025, 9 (01) : 10 - 27
[2] Regiochemical Effects on the Carbohydrate Binding and Selectivity of Flexible Synthetic Carbohydrate Receptors with Indole and Quinoline Heterocyclic Groups
Thakur, Khushabu
Shlain, Milan A.
Marianski, Mateusz
Braunschweig, Adam B.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (37) : 5262 - 5274
[3] Selective carbohydrate recognition by synthetic receptors in aqueous solution
Striegler, S
CURRENT ORGANIC CHEMISTRY, 2003, 7 (01) : 81 - 102
[4] Enantioselective carbohydrate recognition by synthetic lectins in water
Rios, Pablo
Mooibroek, Tiddo J.
Carter, Tom S.
Williams, Christopher
Wilson, Miriam R.
Crump, Matthew P.
Davis, Anthony P.
CHEMICAL SCIENCE, 2017, 8 (05) : 4056 - 4061
[5] Platform Synthetic Lectins for Divalent Carbohydrate Recognition in Water
Carter, Tom S.
Mooibroek, Tiddo J.
Stewart, Patrick F. N.
Crump, Matthew P.
Galan, M. Carmen
Davis, Anthony P.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (32) : 9311 - 9315
[6] Synthesis and Binding of Mannose-Specific Synthetic Carbohydrate Receptors
Bravo, M. Fernando
Palanichamy, Kalanidhi
Shlain, Milan A.
Schiro, Frank
Naeem, Yasir
Marianski, Mateusz
Braunschweig, Adam B.
CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (51) : 11782 - 11795
[7] Carbohydrate recognition by Ca2+-dependent dimeric synthetic receptors
Zheng, Yeting
Schmidt, Bjorn
Braunschweig, Adam
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
[8] Pyrrolic tripodal receptors for carbohydrates. Role of functional groups and binding geometry on carbohydrate recognition
Cacciarini, Martina
Nativi, Cristina
Norcini, Martina
Staderini, Samuele
Francesconi, Oscar
Roelens, Stefano
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (04) : 1085 - 1091
[9] Substituent Effects in Synthetic Lectins - Exploring the Role of CH-π Interactions in Carbohydrate Recognition
Barwell, Nicholas P.
Davis, Anthony P.
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (16): : 6548 - 6557
[10] A role for carbohydrate recognition in mammalian sperm-egg binding
Clark, Gary F.
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 2014, 450 (03) : 1195 - 1203

← 1 2 3 4 5 →