Literature DB >> 10785824

Conformational differences between O- and C-glycosides: the alpha-O-man-(1-->1)-beta-Gal/alpha-C-Man-(1-->1)-beta-Gal case--a decisive demonstration of the importance of the exo-anomeric effect on the conformation of glycosides.

J L Asensio1, F J Cañada, X Cheng, N Khan, D R Mootoo, J Jiménez-Barbero.   

Abstract

The conformational behavior of alpha-O-Man-(1-->1)-beta-Gal (1) and its C-analogue (2) has been studied using J/NOE NMR data, molecular mechanics, molecular dynamics, and ab initio calculations. The population distribution around the glycosidic linkages of 1 and 2 is rather different, especially for the alpha-Man linkage. A lower limit for the exo-anomeric effect in water has been experimentally determined.

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Year:  2000        PMID： 10785824     DOI： 10.1002/(sici)1521-3765(20000317)6:6<1035::aid-chem1035>3.0.co;2-g

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  13 in total

1.  Drude polarizable force field for aliphatic ketones and aldehydes, and their associated acyclic carbohydrates.

Authors:  Meagan C Small; Asaminew H Aytenfisu; Fang-Yu Lin; Xibing He; Alexander D MacKerell
Journal:  J Comput Aided Mol Des       Date:  2017-02-11       Impact factor: 3.686

2.  Synthesis, gp120 binding and anti-HIV activity of fatty acid esters of 1,1-linked disaccharides.

Authors:  Stewart Bachan; Jacques Fantini; Anjali Joshi; Himanshu Garg; David R Mootoo
Journal:  Bioorg Med Chem       Date:  2011-07-01       Impact factor: 3.641

3.  Versatile strategy for the synthesis of biotin-labelled glycans, their immobilization to establish a bioactive surface and interaction studies with a lectin on a biochip.

Authors:  F Javier Muñoz; Angel Rumbero; José V Sinisterra; J Ignacio Santos; Sabine André; Hans-J Gabius; Jesús Jiménez-Barbero; María J Hernáiz
Journal:  Glycoconj J       Date:  2008-03-18       Impact factor: 2.916

4.  NMR studies on the conformation of oligomannosides and their interaction with banana lectin.

Authors:  Caroline Clavel; Angeles Canales; Garima Gupta; J Ignacio Santos; F Javier Cañada; Soledad Penadés; Avadesha Surolia; Jesús Jiménez-Barbero
Journal:  Glycoconj J       Date:  2007-05-11       Impact factor: 2.916

5.  Conformational analysis of a dermatan sulfate-derived tetrasaccharide by NMR, molecular modeling, and residual dipolar couplings.

Authors:  Alba Silipo; Zhenqing Zhang; F Javier Cañada; Antonio Molinaro; Robert J Linhardt; Jesús Jiménez-Barbero
Journal:  Chembiochem       Date:  2008-01-25       Impact factor: 3.164

6.  Synthesis and conformational behavior of the difluoromethylene linked C-glycoside analog of beta-galactopyranosyl-(1<-->1)-alpha-mannopyranoside.

Authors:  Richard W Denton; Kurissery A Tony; José Juan Hernández-Gay; F Javier Cañada; Jesús Jiménez-Barbero; David R Mootoo
Journal:  Carbohydr Res       Date:  2007-06-13       Impact factor: 2.104

7.  Anti-endotoxic activity and structural basis for human MD-2·TLR4 antagonism of tetraacylated lipid A mimetics based on βGlcN(1↔1)αGlcN scaffold.

Authors:  Jose Antonio Garate; Johannes Stöckl; María del Carmen Fernández-Alonso; Daniel Artner; Mira Haegman; Chris Oostenbrink; Jesús Jiménez-Barbero; Rudi Beyaert; Holger Heine; Paul Kosma; Alla Zamyatina
Journal:  Innate Immun       Date:  2014-11-13       Impact factor: 2.680

Review 8.  Mangiferin: a natural miracle bioactive compound against lifestyle related disorders.

Authors:  Muhammad Imran; Muhammad Sajid Arshad; Masood Sadiq Butt; Joong-Ho Kwon; Muhammad Umair Arshad; Muhammad Tauseef Sultan
Journal:  Lipids Health Dis       Date:  2017-05-02       Impact factor: 3.876

9.  The Conformation of the Mannopyranosyl Phosphate Repeating Unit of the Capsular Polysaccharide of Neisseria meningitidis Serogroup A and Its Carba-Mimetic.

Authors:  Ilaria Calloni; Luca Unione; Gonzalo Jiménez-Osés; Francisco Corzana; Linda Del Bino; Alessio Corrado; Olimpia Pitirollo; Cinzia Colombo; Luigi Lay; Roberto Adamo; Jesús Jiménez-Barbero
Journal:  European J Org Chem       Date:  2018-08-17

Review 10.  Bioisosteres of Carbohydrate Functional Groups in Glycomimetic Design.

Authors:  Rachel Hevey
Journal:  Biomimetics (Basel)       Date:  2019-07-28
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