Literature DB >> 33188456

Advances in the Chemical Synthesis of Carbohydrates and Glycoconjugates.

Ankita Malik1,2, Peter H Seeberger1,2, Daniel Varón Silva3,4.   

Abstract

Carbohydrates are functional and structural biomolecules with structures ranging from monosaccharides to polysaccharides. They are naturally found as pure glycans or attached to lipids and proteins forming glycoconjugates. The biosynthesis of carbohydrates is not genetically controlled. The regulation takes place by the expression of enzymes that transfer and hydrolyze the glycan units, leading to glycocojugates having complex mixtures of glycan structures. Chemical synthesis emerged as the best strategy to obtain defined glycan and glycoconjugates and overcome the challenging purification processes. Here, we review the recent advances in the synthesis of oligosaccharides using manual and automated methods. The chapter covers the methods for the preparation of building blocks and control of stereoselectivity and regioselectivity during glycosylations. Finally, it also presents the strategies to obtain natural and non-natural glycoconjugates with lipids and proteins.
© 2020. Springer Nature Switzerland AG.

Entities:  

Keywords:  Carbohydrates; Chemical synthesis; Glycan modifications; Glycoconjugates; Glycoproteins

Year:  2021        PMID: 33188456     DOI: 10.1007/10_2020_150

Source DB:  PubMed          Journal:  Adv Biochem Eng Biotechnol        ISSN: 0724-6145            Impact factor:   2.635


  45 in total

1.  A general strategy for the chemoenzymatic synthesis of asymmetrically branched N-glycans.

Authors:  Zhen Wang; Zoeisha S Chinoy; Shailesh G Ambre; Wenjie Peng; Ryan McBride; Robert P de Vries; John Glushka; James C Paulson; Geert-Jan Boons
Journal:  Science       Date:  2013-07-26       Impact factor: 47.728

Review 2.  Chemical approaches to glycobiology.

Authors:  Laura L Kiessling; Rebecca A Splain
Journal:  Annu Rev Biochem       Date:  2010       Impact factor: 23.643

Review 3.  Chiral reagents in glycosylation and modification of carbohydrates.

Authors:  Hao-Yuan Wang; Stephanie A Blaszczyk; Guozhi Xiao; Weiping Tang
Journal:  Chem Soc Rev       Date:  2018-02-05       Impact factor: 54.564

4.  Synthesis of kojitriose using silicon-tethered glycosidation.

Authors:  M Bols
Journal:  Acta Chem Scand       Date:  1996-10

5.  Synthesis of a glycosylphosphatidylinositol anchor bearing unsaturated lipid chains.

Authors:  Benjamin M Swarts; Zhongwu Guo
Journal:  J Am Chem Soc       Date:  2010-05-19       Impact factor: 15.419

Review 6.  Designing a new antifungal glycoconjugate vaccine.

Authors:  Margaret A Johnson; David R Bundle
Journal:  Chem Soc Rev       Date:  2012-12-11       Impact factor: 54.564

7.  High-efficiency labeling of sialylated glycoproteins on living cells.

Authors:  Ying Zeng; T N C Ramya; Anouk Dirksen; Philip E Dawson; James C Paulson
Journal:  Nat Methods       Date:  2009-02-22       Impact factor: 28.547

8.  Effective sugar nucleotide regeneration for the large-scale enzymatic synthesis of Globo H and SSEA4.

Authors:  Tsung-I Tsai; Hsin-Yu Lee; Shih-Huang Chang; Chia-Hung Wang; Yu-Chen Tu; Yu-Chen Lin; Der-Ren Hwang; Chung-Yi Wu; Chi-Huey Wong
Journal:  J Am Chem Soc       Date:  2013-09-17       Impact factor: 15.419

Review 9.  Synthesis and medical applications of oligosaccharides.

Authors:  Peter H Seeberger; Daniel B Werz
Journal:  Nature       Date:  2007-04-26       Impact factor: 49.962

Review 10.  Biological roles of oligosaccharides: all of the theories are correct.

Authors:  A Varki
Journal:  Glycobiology       Date:  1993-04       Impact factor: 4.313

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