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Literature DB >> 22390569

Acyl and silyl group effects in reactivity-based one-pot glycosylation: synthesis of embryonic stem cell surface carbohydrates Lc4 and IV(2)Fuc-Lc4.

Yun Hsu¹, Xin-An Lu, Medel Manuel L Zulueta, Chih-Ming Tsai, Kuo-I Lin, Shang-Cheng Hung, Chi-Huey Wong.

Abstract

Relative reactivity evaluations showed the graded arming of toluenyl thioglucosides by variously positioned silyl groups but not by their acyl counterparts. These findings were applied in reactivity-based one-pot assembly of linker-attached Lc(4) and IV(2)Fuc-Lc(4), which are components of human embryonic stem cell surface. The sugar-galectin-1 binding was also examined.

Entities: Chemical Gene Species

Mesh：

Substances：
Fucose

Year: 2012 PMID： 22390569 DOI： 10.1021/ja300284x

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

16 in total

1. The one-pot multienzyme (OPME) synthesis of human blood group H antigens and a human milk oligosaccharide (HMOS) with highly active Thermosynechococcus elongates α1-2-fucosyltransferase.

Authors: Chao Zhao; Yijing Wu; Hai Yu; Ishita M Shah; Yanhong Li; Jie Zeng; Bin Liu; David A Mills; Xi Chen
Journal: Chem Commun (Camb) Date: 2016-02-11 Impact factor: 6.222

2. Synthesis of lacto-N-tetraose.

Authors: Kelly M Craft; Steven D Townsend
Journal: Carbohydr Res Date: 2017-02-11 Impact factor: 2.104

3. 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

4. Superarming of glycosyl donors by combined neighboring and conformational effects.

Authors: Mads Heuckendorff; Hemali D Premathilake; Papapida Pornsuriyasak; Anders Ø Madsen; Christian M Pedersen; Mikael Bols; Alexei V Demchenko
Journal: Org Lett Date: 2013-09-05 Impact factor: 6.005

5. Two-step functionalization of oligosaccharides using glycosyl iodide and trimethylene oxide and its applications to multivalent glycoconjugates.

Authors: Hsiao-Wu Hsieh; Ryan A Davis; Jessica A Hoch; Jacquelyn Gervay-Hague
Journal: Chemistry Date: 2014-04-08 Impact factor: 5.236

6. Conformationally superarmed S-ethyl glycosyl donors as effective building blocks for chemoselective oligosaccharide synthesis in one pot.

Authors: Mithila D Bandara; Jagodige P Yasomanee; Nigam P Rath; Christian M Pedersen; Mikael Bols; Alexei V Demchenko
Journal: Org Biomol Chem Date: 2017-01-18 Impact factor: 3.876

Acyl and silyl group effects in reactivity-based one-pot glycosylation: synthesis of embryonic stem cell surface carbohydrates Lc4 and IV(2)Fuc-Lc4.

1. The one-pot multienzyme (OPME) synthesis of human blood group H antigens and a human milk oligosaccharide (HMOS) with highly active Thermosynechococcus elongates α1-2-fucosyltransferase.

2. Synthesis of lacto-N-tetraose.

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

4. Superarming of glycosyl donors by combined neighboring and conformational effects.

5. Two-step functionalization of oligosaccharides using glycosyl iodide and trimethylene oxide and its applications to multivalent glycoconjugates.

6. Conformationally superarmed S-ethyl glycosyl donors as effective building blocks for chemoselective oligosaccharide synthesis in one pot.

7. Regioselective silyl/acetate exchange of disaccharides yields advanced glycosyl donor and acceptor precursors.

8. The chemical synthesis of human milk oligosaccharides: Lacto-N-tetraose (Galβ1→3GlcNAcβ1→3Galβ1→4Glc).

9. A Streamlined Regenerative Glycosylation Reaction: Direct, Acid-Free Activation of Thioglycosides.

Review 10. Human Milk Oligosaccharides (HMOS): Structure, Function, and Enzyme-Catalyzed Synthesis.