Literature DB >> 29969248

Catalytic Glycosylations in Oligosaccharide Synthesis.

Michael Martin Nielsen1, Christian Marcus Pedersen1.   

Abstract

Catalytic glycosylation has been a central reaction in carbohydrate chemistry since its introduction by Fischer 125 years ago, but it is only in the past three to four decades that catalytic methods for synthesizing oligosaccharides have appeared. Despite the development of numerous elegant and ingenious catalytic glycosylation methods, only a few are in general use. This review covers all methods of catalytic glycosylation with the focus on the development and application in oligosaccharide synthesis and provide an overview of the scope and limitations of these. The review also includes relevant mechanistic studies of catalytic glycosylations. The future of catalytic glycosylation chemistry is discussed, including specific, upcoming methods and possible directions for the field of research in general.

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Year:  2018        PMID: 29969248     DOI: 10.1021/acs.chemrev.8b00144

Source DB:  PubMed          Journal:  Chem Rev        ISSN: 0009-2665            Impact factor:   60.622


  29 in total

Review 1.  Oligosaccharide Synthesis and Translational Innovation.

Authors:  Larissa Krasnova; Chi-Huey Wong
Journal:  J Am Chem Soc       Date:  2019-02-18       Impact factor: 15.419

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

3.  Recent Developments in Stereoselective Chemical Glycosylation.

Authors:  Jesse Ling; Clay S Bennett
Journal:  Asian J Org Chem       Date:  2019-05-02       Impact factor: 3.319

4.  Stereospecific Furanosylations Catalyzed by Bis-thiourea Hydrogen-Bond Donors.

Authors:  Andrew B Mayfield; Jan B Metternich; Adam H Trotta; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2020-02-14       Impact factor: 15.419

Review 5.  Harnessing glycoenzyme engineering for synthesis of bioactive oligosaccharides.

Authors:  Mounir Benkoulouche; Régis Fauré; Magali Remaud-Siméon; Claire Moulis; Isabelle André
Journal:  Interface Focus       Date:  2019-02-15       Impact factor: 3.906

6.  Site-Selective and Stereoselective O-Alkylation of Glycosides by Rh(II)-Catalyzed Carbenoid Insertion.

Authors:  Jicheng Wu; Xiaolei Li; Xiaotian Qi; Xiyan Duan; Weston L Cracraft; Ilia A Guzei; Peng Liu; Weiping Tang
Journal:  J Am Chem Soc       Date:  2019-12-03       Impact factor: 15.419

7.  Fluoride Migration Catalysis Enables Simple, Stereoselective, and Iterative Glycosylation.

Authors:  Girish C Sati; Joshua L Martin; Yishu Xu; Tanmay Malakar; Paul M Zimmerman; John Montgomery
Journal:  J Am Chem Soc       Date:  2020-04-01       Impact factor: 15.419

8.  Anthranilic Acid as a Versatile Fluorescent Tag and Linker for Functional Glycomics.

Authors:  Yuyang Zhu; Xueyun Liu; Ying Zhang; Zhongfu Wang; Yi Lasanajak; Xuezheng Song
Journal:  Bioconjug Chem       Date:  2018-11-12       Impact factor: 4.774

9.  Phenanthroline-Catalyzed Stereoretentive Glycosylations.

Authors:  Fei Yu; Jiayi Li; Paul M DeMent; Yi-Jung Tu; H Bernhard Schlegel; Hien M Nguyen
Journal:  Angew Chem Int Ed Engl       Date:  2019-04-09       Impact factor: 15.336

10.  Palladium(II)-assisted activation of thioglycosides.

Authors:  Samira Escopy; Yashapal Singh; Alexei V Demchenko
Journal:  Org Biomol Chem       Date:  2021-03-11       Impact factor: 3.876

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