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Literature DB >> 24382624

Modulating glycosylation with exogenous nucleophiles: an overview.

Shaheen K Mulani¹, Wei-Cheng Hung, Arun B Ingle, Kai-Sheng Shiau, Kwok-Kong Tony Mong.

Abstract

The major challenge in carbohydrate synthesis is stereochemical control of glycosidic bond formation. Different glycosylation methods have been developed that are based on the modulation effect of external nucleophiles. This review highlights the development, synthetic application, challenges and outlook of the modulated glycosylation methods.

Entities: Chemical

Mesh：

Substances：
Glycosides

Year: 2014 PMID： 24382624 DOI： 10.1039/c3ob42129e

Source DB: PubMed Journal: Org Biomol Chem ISSN： 1477-0520 Impact factor: 3.876

Keyword Cloud
Cited

10 in total

Review 1. Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.

Authors: Matteo Panza; Salvatore G Pistorio; Keith J Stine; Alexei V Demchenko
Journal: Chem Rev Date: 2018-06-28 Impact factor: 60.622

2. Pre-activation Based Stereoselective Glycosylations.

Authors: Bo Yang; Weizhun Yang; Sherif Ramadan; Xuefei Huang
Journal: European J Org Chem Date: 2017-12-28

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. Rapid assembly of the doubly-branched pentasaccharide domain of the immunoadjuvant jujuboside A via convergent B(C₆F₅)₃-catalyzed glycosylation of sterically-hindered precursors.

Authors: Rashad R Karimov; Derek S Tan; David Y Gin
Journal: Chem Commun (Camb) Date: 2017-05-30 Impact factor: 6.222

5. Mapping the Reactivity and Selectivity of 2-Azidofucosyl Donors for the Assembly of N-Acetylfucosamine-Containing Bacterial Oligosaccharides.

Authors: Bas Hagen; Sara Ali; Herman S Overkleeft; Gijsbert A van der Marel; Jeroen D C Codée
Journal: J Org Chem Date: 2017-01-10 Impact factor: 4.354

Modulating glycosylation with exogenous nucleophiles: an overview.

Review 1. Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.

2. Pre-activation Based Stereoselective Glycosylations.

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

4. Rapid assembly of the doubly-branched pentasaccharide domain of the immunoadjuvant jujuboside A via convergent B(C₆F₅)₃-catalyzed glycosylation of sterically-hindered precursors.

5. Mapping the Reactivity and Selectivity of 2-Azidofucosyl Donors for the Assembly of N-Acetylfucosamine-Containing Bacterial Oligosaccharides.

Review 6. A propos of glycosyl cations and the mechanism of chemical glycosylation; the current state of the art.

Review 7. Chemical O-Glycosylations: An Overview.

8. Automated assembly of oligosaccharides containing multiple cis-glycosidic linkages.

9. Reagent Controlled Stereoselective Synthesis of α-Glucans.

Review 10. Anomeric O-Functionalization of Carbohydrates for Chemical Conjugation to Vaccine Constructs.

Modulating glycosylation with exogenous nucleophiles: an overview.

Review 1. Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.

2. Pre-activation Based Stereoselective Glycosylations.

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

4. Rapid assembly of the doubly-branched pentasaccharide domain of the immunoadjuvant jujuboside A via convergent B(C6F5)3-catalyzed glycosylation of sterically-hindered precursors.

5. Mapping the Reactivity and Selectivity of 2-Azidofucosyl Donors for the Assembly of N-Acetylfucosamine-Containing Bacterial Oligosaccharides.

Review 6. A propos of glycosyl cations and the mechanism of chemical glycosylation; the current state of the art.

Review 7. Chemical O-Glycosylations: An Overview.

8. Automated assembly of oligosaccharides containing multiple cis-glycosidic linkages.

9. Reagent Controlled Stereoselective Synthesis of α-Glucans.

Review 10. Anomeric O-Functionalization of Carbohydrates for Chemical Conjugation to Vaccine Constructs.

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

4. Rapid assembly of the doubly-branched pentasaccharide domain of the immunoadjuvant jujuboside A via convergent B(C₆F₅)₃-catalyzed glycosylation of sterically-hindered precursors.