Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Glycosidic bond formation in aqueous solution: on the oxocarbenium intermediate.

Literature DB >> 12952477

Glycosidic bond formation in aqueous solution: on the oxocarbenium intermediate.

Abstract

The mechanism of specific acid-catalyzed glycosidic bond formation between methanol and alpha-d-glucopyranoside in aqueous solution at 300 K was studied using Car-Parrinello molecular dynamics. The reaction was found to proceed through a non-solvent equilibrated oxocarbenium cation intermediate characterized by the loss of a hydrogen-bonding interaction between the ring oxygen and solvating water. The mechanism, which was found to be D(N)A(N) in nature, is discussed in detail.

Entities: Chemical

Mesh：

Substances：

Year: 2003 PMID： 12952477 DOI： 10.1021/ja035600n

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

Keyword Cloud
Cited

6 in total

1. Aqueous Glycosylation of Unprotected Sucrose Employing Glycosyl Fluorides in the Presence of Calcium Ion and Trimethylamine.

Authors: Guillaume Pelletier; Aaron Zwicker; C Liana Allen; Alanna Schepartz; Scott J Miller
Journal: J Am Chem Soc Date: 2016-03-01 Impact factor: 15.419

2. Hydrogen-bonding catalysis and inhibition by simple solvents in the stereoselective kinetic epoxide-opening spirocyclization of glycal epoxides to form spiroketals.

Authors: Jacqueline M Wurst; Guodong Liu; Derek S Tan
Journal: J Am Chem Soc Date: 2011-05-03 Impact factor: 15.419

Review 3. Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century.

Authors: Yashapal Singh; Scott A Geringer; Alexei V Demchenko
Journal: Chem Rev Date: 2022-06-08 Impact factor: 72.087

Glycosidic bond formation in aqueous solution: on the oxocarbenium intermediate.

1. Aqueous Glycosylation of Unprotected Sucrose Employing Glycosyl Fluorides in the Presence of Calcium Ion and Trimethylamine.

2. Hydrogen-bonding catalysis and inhibition by simple solvents in the stereoselective kinetic epoxide-opening spirocyclization of glycal epoxides to form spiroketals.

Review 3. Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century.

4. Rapid phenolic O-glycosylation of small molecules and complex unprotected peptides in aqueous solvent.

5. Ab Initio Molecular Dynamics Simulations of the S_N1/S_N2 Mechanistic Continuum in Glycosylation Reactions.

6. ADP-Ribosylargininyl reaction of cholix toxin is mediated through diffusible intermediates.

Glycosidic bond formation in aqueous solution: on the oxocarbenium intermediate.

1. Aqueous Glycosylation of Unprotected Sucrose Employing Glycosyl Fluorides in the Presence of Calcium Ion and Trimethylamine.

2. Hydrogen-bonding catalysis and inhibition by simple solvents in the stereoselective kinetic epoxide-opening spirocyclization of glycal epoxides to form spiroketals.

Review 3. Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century.

4. Rapid phenolic O-glycosylation of small molecules and complex unprotected peptides in aqueous solvent.

5. Ab Initio Molecular Dynamics Simulations of the SN1/SN2 Mechanistic Continuum in Glycosylation Reactions.

6. ADP-Ribosylargininyl reaction of cholix toxin is mediated through diffusible intermediates.

5. Ab Initio Molecular Dynamics Simulations of the S_N1/S_N2 Mechanistic Continuum in Glycosylation Reactions.