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Literature DB >> 25108484

A propos of glycosyl cations and the mechanism of chemical glycosylation; the current state of the art.

Abstract

An overview of recent advances in glycosylation with particular emphasis on mechanism is presented. The mounting evidence for both the existence of glycosyl oxocarbenium ions as fleeting intermediates in some reactions, and the crucial role of the associated counterion in others is discussed. The extremes of the SN1 and SN2 manifolds for the glycosylation reaction are bridged by a continuum of mechanisms in which it appears likely that most examples are located.

Entities: Chemical Disease Gene Species

Keywords: Counter ions; Hydrogen bonding; Kinetics; Oxocarbenium ions

Mesh：

Substances：
Glycosides

Year: 2014 PMID： 25108484 PMCID： PMC4281519 DOI： 10.1016/j.carres.2014.06.020

Source DB: PubMed Journal: Carbohydr Res ISSN： 0008-6215 Impact factor: 2.104

66 in total

1. Highly beta-selective O-glucosidation due to the restricted twist-boat conformation.

Authors: Yasunori Okada; Tatsuya Mukae; Kotaro Okajima; Miyoko Taira; Mari Fujita; Hidetoshi Yamada
Journal: Org Lett Date: 2007-03-15 Impact factor: 6.005

Review 2. Going to extremes: "super" armed glycosyl donors in glycosylation chemistry.

Authors: Henrik H Jensen; Christian Marcus Pedersen; Mikael Bols
Journal: Chemistry Date: 2007 Impact factor: 5.236

3. Dimethylformamide: an unusual glycosylation modulator.

Authors: Shao-Ru Lu; Yen-Hsun Lai; Jiun-Han Chen; Chih-Yueh Liu; Kwok-Kong Tony Mong
Journal: Angew Chem Int Ed Engl Date: 2011-06-17 Impact factor: 15.336

4. Visible light mediated activation and O-glycosylation of thioglycosides.

Authors: Walter J Wever; Maris A Cinelli; Albert A Bowers
Journal: Org Lett Date: 2012-12-20 Impact factor: 6.005

5. Indirect cation-flow method: flash generation of alkoxycarbenium ions and studies on the stability of glycosyl cations.

Authors: Kodai Saito; Koji Ueoka; Kouichi Matsumoto; Seiji Suga; Toshiki Nokami; Jun-ichi Yoshida
Journal: Angew Chem Int Ed Engl Date: 2011-04-20 Impact factor: 15.336

6. Plausible Transition States for glycosylation reactions.

Authors: Dennis M Whitfield
Journal: Carbohydr Res Date: 2012-04-06 Impact factor: 2.104

7. Glycosyl sulfonium ions as storable intermediates for glycosylations.

Authors: Toshiki Nokami; Yuki Nozaki; Yoshihiro Saigusa; Akito Shibuya; Shino Manabe; Yukishige Ito; Jun-ichi Yoshida
Journal: Org Lett Date: 2011-02-16 Impact factor: 6.005

8. Theoretical Investigation of Solvent Effects on Glycosylation Reactions: Stereoselectivity Controlled by Preferential Conformations of the Intermediate Oxacarbenium-Counterion Complex.

Authors: Hiroko Satoh; Halvor S Hansen; Shino Manabe; Wilfred F van Gunsteren; Philippe H Hünenberger
Journal: J Chem Theory Comput Date: 2010-06-08 Impact factor: 6.006

9. Tuning effect of silyl protecting groups on the glycosylation reactivity of arabinofuranosyl thioglycosides.

Authors: Xing-Yong Liang; Hua-Chao Bin; Jin-Song Yang
Journal: Org Lett Date: 2013-05-17 Impact factor: 6.005

10. Does neighboring group participation by non-vicinal esters play a role in glycosylation reactions? Effective probes for the detection of bridging intermediates.

Authors: David Crich; Tianshun Hu; Feng Cai
Journal: J Org Chem Date: 2008-10-22 Impact factor: 4.354

32 in total

1. Stereoselectivity of Conformationally Restricted Glucosazide Donors.

Authors: Stefan van der Vorm; Herman S Overkleeft; Gijsbert A van der Marel; Jeroen D C Codée
Journal: J Org Chem Date: 2017-04-25 Impact factor: 4.354

2. Mechanisms of Stereodirecting Participation and Ester Migration from Near and Far in Glycosylation and Related Reactions.

Authors: Asiri A Hettikankanamalage; Robert Lassfolk; Filip S Ekholm; Reko Leino; David Crich
Journal: Chem Rev Date: 2020-07-05 Impact factor: 60.622

Review 3. The Experimental Evidence in Support of Glycosylation Mechanisms at the S_N1-S_N2 Interface.

Authors: Philip Ouma Adero; Harsha Amarasekara; Peng Wen; Luis Bohé; David Crich
Journal: Chem Rev Date: 2018-05-30 Impact factor: 60.622

4. Synthesis and intramolecular glycosylation of sialyl mono-esters of o-xylylene glycol. The importance of donor configuration and nitrogen protecting groups on cyclization yield and selectivity; isolation and characterization of a N-sialyl acetamide indicative of participation by acetonitrile.

Authors: Harsha Amarasekara; David Crich
Journal: Carbohydr Res Date: 2016-10-08 Impact factor: 2.104

5. One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates.

Authors: D Jamin Keith; Stefan A Marasligiller; Alexander W Sasse; Steven D Townsend
Journal: J Vis Exp Date: 2018-01-15 Impact factor: 1.355

6. Synthesis of glycoimmunogen Tn-Thr-PS A1 via hydrazone bond and stability optimization of PS A1 monosaccharide mimics under vaccine development conditions.

Authors: F Hossain; S Nishat; S Ghosh; S Boga; G T Hymel; P R Andreana
Journal: J Carbohydr Chem Date: 2020-02-03 Impact factor: 1.667

7. Synthesis of the Hexasaccharide Fragment of Landomycin A Using a Mild, Reagent-Controlled Approach.

Authors: Subbarao Yalamanchili; Dina Lloyd; Clay S Bennett
Journal: Org Lett Date: 2019-04-25 Impact factor: 6.005

8. Divergent Chemoenzymatic Synthesis of Asymmetrical-Core-Fucosylated and Core-Unmodified N-Glycans.

Authors: Tiehai Li; Min Huang; Lin Liu; Shuo Wang; Kelley W Moremen; Geert-Jan Boons
Journal: Chemistry Date: 2016-11-22 Impact factor: 5.236

9. Further studies on cation clock reactions in glycosylation: observation of a configuration specific intramolecular sulfenyl transfer and isolation and characterization of a tricyclic acetal.

Authors: Min Huang; Takayuki Furukawa; Pascal Retailleau; David Crich; Luis Bohé
Journal: Carbohydr Res Date: 2016-04-06 Impact factor: 2.104

10. Blue Light Photocatalytic Glycosylation without Electrophilic Additives.

Authors: Peng Wen; David Crich
Journal: Org Lett Date: 2017-04-24 Impact factor: 6.005

Review 2. Going to extremes: "super" armed glycosyl donors in glycosylation chemistry.

Review 3. The Experimental Evidence in Support of Glycosylation Mechanisms at the SN1-SN2 Interface.

Review 3. The Experimental Evidence in Support of Glycosylation Mechanisms at the S_N1-S_N2 Interface.