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Literature DB >> 14719939

Synthesis of heparin oligosaccharides.

Jinq-Chyi Lee¹, Xin-An Lu, Suvarn S Kulkarni, Yuh-Sheng Wen, Shang-Cheng Hung.

Abstract

An efficient preparation of rare 2-O-benzoyl-3-O-benzyl-1,6-anhydro-beta-l-idopyranose from commercially available diacetone alpha-d-glucose in five straightforward steps is described here. With this key building block in hand, the total syntheses of heparin oligosaccharides with three, five, seven, and nine sugar units are successfully carried out.

Entities: Chemical

Mesh：

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Year: 2004 PMID： 14719939 DOI： 10.1021/ja038244h

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

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Cited

28 in total

1. A facile method for oxidation of primary alcohols to carboxylic acids and its application in glycosaminoglycan syntheses.

Authors: Lijun Huang; Nardos Teumelsan; Xuefei Huang
Journal: Chemistry Date: 2006-07-05 Impact factor: 5.236

2. Directing the biological activities of heparan sulfate oligosaccharides using a chemoenzymatic approach.

Authors: Yongmei Xu; Zhen Wang; Renpeng Liu; Arlene S Bridges; Xuefei Huang; Jian Liu
Journal: Glycobiology Date: 2011-08-11 Impact factor: 4.313

3. 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

4. Preactivation-based, one-pot combinatorial synthesis of heparin-like hexasaccharides for the analysis of heparin-protein interactions.

Authors: Zhen Wang; Yongmei Xu; Bo Yang; Gopinath Tiruchinapally; Bin Sun; Renpeng Liu; Steven Dulaney; Jian Liu; Xuefei Huang
Journal: Chemistry Date: 2010-07-26 Impact factor: 5.236

Synthesis of heparin oligosaccharides.

1. A facile method for oxidation of primary alcohols to carboxylic acids and its application in glycosaminoglycan syntheses.

2. Directing the biological activities of heparan sulfate oligosaccharides using a chemoenzymatic approach.

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

4. Preactivation-based, one-pot combinatorial synthesis of heparin-like hexasaccharides for the analysis of heparin-protein interactions.

5. Facile chemoenzymatic synthesis of biotinylated heparosan hexasaccharide.

6. Chemical Sulfation of Small Molecules - Advances and Challenges.

7. Modular synthesis of heparan sulfate oligosaccharides for structure-activity relationship studies.

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

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

10. Using an enzymatic combinatorial approach to identify anticoagulant heparan sulfate structures.