Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Glycomimetic building blocks: a divergent synthesis of epimers of shikimic acid.

Literature DB >> 21711006

Glycomimetic building blocks: a divergent synthesis of epimers of shikimic acid.

Joseph C Grim¹, Kathleen C A Garber, Laura L Kiessling.

Abstract

A divergent synthesis of (-)-4-epi-shikimic acid was developed. This route features a one-pot zinc-mediated reductive ring opening of an arabinofuranose followed by a Barbier reaction and culminates in a ring-closing metathesis. Functionalization of (-)-4-epi-shikimic acid via conjugate addition of a thiol occurs in high diastereoselectivity to afford a product with the features of fucosylated glycans.

Entities: Chemical Disease Gene Species

Mesh：

Substances：

Year: 2011 PMID： 21711006 PMCID： PMC3166631 DOI： 10.1021/ol201252x

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

20 in total

1. Parallel synthesis of glycomimetic libraries: targeting a C-type lectin.

Authors: Michael C Schuster; David A Mann; Tonia J Buchholz; Kathryn M Johnson; William D Thomas; Laura L Kiessling
Journal: Org Lett Date: 2003-05-01 Impact factor: 6.005

2. Structural basis for distinct ligand-binding and targeting properties of the receptors DC-SIGN and DC-SIGNR.

Authors: Yuan Guo; Hadar Feinberg; Edward Conroy; Daniel A Mitchell; Richard Alvarez; Ola Blixt; Maureen E Taylor; William I Weis; Kurt Drickamer
Journal: Nat Struct Mol Biol Date: 2004-06-13 Impact factor: 15.369

Review 3. Self- and nonself-recognition by C-type lectins on dendritic cells.

Authors: Teunis B H Geijtenbeek; Sandra J van Vliet; Anneke Engering; Bert A 't Hart; Yvette van Kooyk
Journal: Annu Rev Immunol Date: 2004 Impact factor: 28.527

4. Glycomimetics and glycodendrimers as high affinity microbial anti-adhesins.

Authors: Anne Imberty; Yoann M Chabre; René Roy
Journal: Chemistry Date: 2008 Impact factor: 5.236

Review 5. Chemical approaches to glycobiology.

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

6. Highly efficient ruthenium catalysts for the formation of tetrasubstituted olefins via ring-closing metathesis.

Authors: Ian C Stewart; Thay Ung; Alexandre A Pletnev; Jacob M Berlin; Robert H Grubbs; Yann Schrodi
Journal: Org Lett Date: 2007-03-23 Impact factor: 6.005

7. Survey of immune-related, mannose/fucose-binding C-type lectin receptors reveals widely divergent sugar-binding specificities.

Authors: Reiko T Lee; Tsui-Ling Hsu; Shau Ku Huang; Shie-Liang Hsieh; Chi-Huey Wong; Yuan C Lee
Journal: Glycobiology Date: 2010-11-26 Impact factor: 4.313

Glycomimetic building blocks: a divergent synthesis of epimers of shikimic acid.

1. Parallel synthesis of glycomimetic libraries: targeting a C-type lectin.

2. Structural basis for distinct ligand-binding and targeting properties of the receptors DC-SIGN and DC-SIGNR.

Review 3. Self- and nonself-recognition by C-type lectins on dendritic cells.

4. Glycomimetics and glycodendrimers as high affinity microbial anti-adhesins.

Review 5. Chemical approaches to glycobiology.

6. Highly efficient ruthenium catalysts for the formation of tetrasubstituted olefins via ring-closing metathesis.

7. Survey of immune-related, mannose/fucose-binding C-type lectin receptors reveals widely divergent sugar-binding specificities.

8. A general glycomimetic strategy yields non-carbohydrate inhibitors of DC-SIGN.

9. Inhibition of DC-SIGN-mediated HIV infection by a linear trimannoside mimic in a tetravalent presentation.

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

1. Quinoxalinone Inhibitors of the Lectin DC-SIGN.

2. Noncarbohydrate glycomimetics and glycoprotein surrogates as DC-SIGN antagonists and agonists.