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Literature DB >> 16235966

Orthogonal sulfation strategy for synthetic heparan sulfate ligands.

Ren-Hua Fan¹, Jihane Achkar, Jesús M Hernández-Torres, Alexander Wei.

Abstract

[reaction: see text] An orthogonal sulfation strategy involving six different protecting groups has been developed for generating sulfated carbohydrate libraries based on heparan. Chemoselective cleavage conditions (optimized for a heparan disaccharide) can be performed in the presence of sulfate esters as well as the remaining protecting groups.

Entities: Chemical

Mesh：

Substances：

Year: 2005 PMID： 16235966 PMCID： PMC1851889 DOI： 10.1021/ol052130o

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

30 in total

1. Conversion of D-glucals into L-glycals and mirror-image carbohydrates.

Authors: Fabien P Boulineau; Alexander Wei
Journal: Org Lett Date: 2004-01-08 Impact factor: 6.005

2. Structural requirement of heparan sulfate for interaction with herpes simplex virus type 1 virions and isolated glycoprotein C.

Authors: E Feyzi; E Trybala; T Bergström; U Lindahl; D Spillmann
Journal: J Biol Chem Date: 1997-10-03 Impact factor: 5.157

3. Syntheses of the methyl glycosides of the repeating units of chondroitin 4- and 6-sulfate.

Authors: J C Jacquinet
Journal: Carbohydr Res Date: 1990-06-01 Impact factor: 2.104

Review 4. Glycosaminoglycans and their binding to biological macromolecules.

Authors: U Lindahl; M Höök
Journal: Annu Rev Biochem Date: 1978 Impact factor: 23.643

Review 5. Cell-surface glycosaminoglycans.

Authors: M Höök; L Kjellén; S Johansson
Journal: Annu Rev Biochem Date: 1984 Impact factor: 23.643

6. New set of orthogonal protecting groups for the modular synthesis of heparan sulfate fragments.

Authors: Arati Prabhu; Andre Venot; Geert-Jan Boons
Journal: Org Lett Date: 2003-12-25 Impact factor: 6.005

7. Synthesis of heparin-like oligosaccharides on polymer supports.

Authors: Rafael Ojeda; Olimpia Terentí; José-Luis de Paz; Manuel Martín-Lomas
Journal: Glycoconj J Date: 2004 Impact factor: 2.916

8. Synthesis of tailor-made glycoconjugate mimetics of heparan sulfate that bind IFN-gamma in the nanomolar range.

Authors: André Lubineau; Hugues Lortat-Jacob; Ollivier Gavard; Stéphane Sarrazin; David Bonnaffé
Journal: Chemistry Date: 2004-09-06 Impact factor: 5.236

9. Temperature-controlled regioselectivity in the reductive cleavage of p-methoxybenzylidene acetals.

Authors: Jesús M Hernández-Torres; Jihane Achkar; Alexander Wei
Journal: J Org Chem Date: 2004-10-15 Impact factor: 4.354

10. Identification of structural features of heparin required for inhibition of herpes simplex virus type 1 binding.

Authors: B C Herold; S I Gerber; T Polonsky; B J Belval; P N Shaklee; K Holme
Journal: Virology Date: 1995-02-01 Impact factor: 3.616

15 in total

1. Sulfoform generation from an orthogonally protected disaccharide.

Authors: Runhui Liu; Oscar Morales-Collazo; Alexander Wei
Journal: Carbohydr Res Date: 2012-04-21 Impact factor: 2.104

2. Towards the assembly of heparin and heparan sulfate oligosaccharide libraries: efficient synthesis of uronic acid and disaccharide building blocks.

Authors: Akihiro Saito; Masahiro Wakao; Hiroshi Deguchi; Aya Mawatari; Michael Sobel; Yasuo Suda
Journal: Tetrahedron Date: 2010-05-29 Impact factor: 2.457

Orthogonal sulfation strategy for synthetic heparan sulfate ligands.

1. Conversion of D-glucals into L-glycals and mirror-image carbohydrates.

2. Structural requirement of heparan sulfate for interaction with herpes simplex virus type 1 virions and isolated glycoprotein C.

3. Syntheses of the methyl glycosides of the repeating units of chondroitin 4- and 6-sulfate.

Review 4. Glycosaminoglycans and their binding to biological macromolecules.

Review 5. Cell-surface glycosaminoglycans.

6. New set of orthogonal protecting groups for the modular synthesis of heparan sulfate fragments.

7. Synthesis of heparin-like oligosaccharides on polymer supports.

8. Synthesis of tailor-made glycoconjugate mimetics of heparan sulfate that bind IFN-gamma in the nanomolar range.

9. Temperature-controlled regioselectivity in the reductive cleavage of p-methoxybenzylidene acetals.

10. Identification of structural features of heparin required for inhibition of herpes simplex virus type 1 binding.

1. Sulfoform generation from an orthogonally protected disaccharide.

2. Towards the assembly of heparin and heparan sulfate oligosaccharide libraries: efficient synthesis of uronic acid and disaccharide building blocks.

3. Rapid and efficient microwave-assisted synthesis of highly sulfated organic scaffolds.

4. Chemical synthesis of syndecan-3 glycopeptides bearing two heparan sulfate glycan chains.

5. Obstacles and solutions for chemical synthesis of syndecan-3 (53-62) glycopeptides with two heparan sulfate chains.

6. Divergent heparin oligosaccharide synthesis with preinstalled sulfate esters.

7. Chemical synthesis of a heparan sulfate glycopeptide: syndecan-1.

8. Anomeric reactivity-based one-pot synthesis of heparin-like oligosaccharides.

9. Solid-phase synthesis of alpha-glucosamine sulfoforms with fragmentation analysis by tandem mass spectrometry.

Review 10. Strategies in synthesis of heparin/heparan sulfate oligosaccharides: 2000-present.