Literature DB >> 19833544

Recent progress in chemical and chemoenzymatic synthesis of carbohydrates.

Saddam Muthana1, Hongzhi Cao, Xi Chen.   

Abstract

The important roles that carbohydrates play in biological processes and their potential application in diagnosis, therapeutics, and vaccine development have made them attractive synthetic targets. Despite ongoing challenges, tremendous progresses have been made in recent years for the synthesis of carbohydrates. The chemical glycosylation methods have become more sophisticated and the synthesis of oligosaccharides has become more predictable. Simplified one-pot glycosylation strategy and automated synthesis are increasingly used to obtain biologically important glycans. On the other hand, chemoenzymatic synthesis continues to be a powerful alternative for obtaining complex carbohydrates. This review highlights recent progress in chemical and chemoenzymatic synthesis of carbohydrates with a particular focus on the methods developed for the synthesis of oligosaccharides, polysaccharides, glycolipids, and glycosylated natural products.

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Year:  2009        PMID: 19833544      PMCID: PMC3097241          DOI: 10.1016/j.cbpa.2009.09.013

Source DB:  PubMed          Journal:  Curr Opin Chem Biol        ISSN: 1367-5931            Impact factor:   8.822


  54 in total

1.  Syntheses of Lewis(x) and dimeric Lewis(x): construction of branched oligosaccharides by a combination of preactivation and reactivity based chemoselective one-pot glycosylations.

Authors:  Adeline Miermont; Youlin Zeng; Yuqing Jing; Xin-shan Ye; Xuefei Huang
Journal:  J Org Chem       Date:  2007-10-16       Impact factor: 4.354

2.  Chemoenzymatic synthesis of a new class of macrocyclic oligosaccharides.

Authors:  Saddam Muthana; Hai Yu; Hongzhi Cao; Jiansong Cheng; Xi Chen
Journal:  J Org Chem       Date:  2009-04-17       Impact factor: 4.354

3.  4-(pyridin-2-yl)thiazol-2-yl thioglycosides as bidentate ligands for oligosaccharide synthesis via temporary deactivation.

Authors:  Papapida Pornsuriyasak; Nigam P Rath; Alexei V Demchenko
Journal:  Chem Commun (Camb)       Date:  2008-10-01       Impact factor: 6.222

4.  Efficient synthesis of an alpha(2,9) trisialic acid by one-pot glycosylation and polymer-assisted deprotection.

Authors:  Hiroshi Tanaka; Yusuke Tateno; Yuji Nishiura; Takashi Takahashi
Journal:  Org Lett       Date:  2008-12-18       Impact factor: 6.005

5.  One-pot synthesis of oligosaccharides by combining reductive openings of benzylidene acetals and glycosylations.

Authors:  Yusuf Vohra; Mahalakshmi Vasan; Andre Venot; Geert-Jan Boons
Journal:  Org Lett       Date:  2008-06-26       Impact factor: 6.005

6.  Oligomannan synthesis using ionic liquid supported glycosylation.

Authors:  Ashish K Pathak; Charu K Yerneni; Zac Young; Vibha Pathak
Journal:  Org Lett       Date:  2007-12-11       Impact factor: 6.005

7.  Protecting group free glycosidations using p-toluenesulfonohydrazide donors.

Authors:  Anna V Gudmundsdottir; Mark Nitz
Journal:  Org Lett       Date:  2008-07-11       Impact factor: 6.005

8.  Multi-component one-pot synthesis of the tumor-associated carbohydrate antigen Globo-H based on preactivation of thioglycosyl donors.

Authors:  Zhen Wang; Luyuan Zhou; Kheireddine El-Boubbou; Xin-shan Ye; Xuefei Huang
Journal:  J Org Chem       Date:  2007-07-21       Impact factor: 4.354

9.  Enzymatic synthesis of gentiooligosaccharides by transglycosylation with beta-glycosidases from Penicillium multicolor.

Authors:  Yoshinori Fujimoto; Takeshi Hattori; Shuji Uno; Takeomi Murata; Taichi Usui
Journal:  Carbohydr Res       Date:  2009-03-12       Impact factor: 2.104

10.  Combinatorial chemoenzymatic synthesis and high-throughput screening of sialosides.

Authors:  Harshal A Chokhawala; Shengshu Huang; Kam Lau; Hai Yu; Jiansong Cheng; Vireak Thon; Nancy Hurtado-Ziola; Juan A Guerrero; Ajit Varki; Xi Chen
Journal:  ACS Chem Biol       Date:  2008-08-27       Impact factor: 5.100

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  34 in total

1.  Cloning and characterization of a viral α2-3-sialyltransferase (vST3Gal-I) for the synthesis of sialyl Lewisx.

Authors:  Go Sugiarto; Kam Lau; Hai Yu; Stephanie Vuong; Vireak Thon; Yanhong Li; Shengshu Huang; Xi Chen
Journal:  Glycobiology       Date:  2010-10-26       Impact factor: 4.313

Review 2.  Glycosyltransferase engineering for carbohydrate synthesis.

Authors:  John B McArthur; Xi Chen
Journal:  Biochem Soc Trans       Date:  2016-02       Impact factor: 5.407

3.  Immobilization of glycans on solid surfaces for application in glycomics.

Authors:  Crystal L O'Neil; Keith J Stine; Alexei V Demchenko
Journal:  J Carbohydr Chem       Date:  2018-04-27       Impact factor: 1.667

Review 4.  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

Review 5.  Endoglycosidases for the Synthesis of Polysaccharides and Glycoconjugates.

Authors:  Chao Li; Lai-Xi Wang
Journal:  Adv Carbohydr Chem Biochem       Date:  2016-08-23       Impact factor: 12.200

6.  Cultivating healthy growth and nutrition through the gut microbiota.

Authors:  Sathish Subramanian; Laura V Blanton; Steven A Frese; Mark Charbonneau; David A Mills; Jeffrey I Gordon
Journal:  Cell       Date:  2015-03-26       Impact factor: 41.582

Review 7.  Expeditious oligosaccharide synthesis via selective, semi-orthogonal, and orthogonal activation.

Authors:  Sophon Kaeothip; Alexei V Demchenko
Journal:  Carbohydr Res       Date:  2011-05-18       Impact factor: 2.104

8.  Chemoenzymatic synthesis of α-dystroglycan core M1 O-mannose glycans.

Authors:  Yan Zhang; Caicai Meng; Lan Jin; Xi Chen; Fengshan Wang; Hongzhi Cao
Journal:  Chem Commun (Camb)       Date:  2015-06-23       Impact factor: 6.222

Review 9.  Chemical and chemoenzymatic synthesis of glycoproteins for deciphering functions.

Authors:  Lai-Xi Wang; Mohammed N Amin
Journal:  Chem Biol       Date:  2014-01-16

Review 10.  Chemoenzymatic Methods for the Synthesis of Glycoproteins.

Authors:  Chao Li; Lai-Xi Wang
Journal:  Chem Rev       Date:  2018-08-24       Impact factor: 60.622

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