Synthesis and interaction with midkine of biotinylated chondroitin sulfate tetrasaccharides

Regiospecifically sulfated chondroitin sulfate repeating tetrasaccharides, CS-OO, GlcAβ-GalNAcβ-GlcAβ-GalNAcβ; CS-EE, GlcAβ-GalNAc(4S6S)β-GlcAβ-GalNAc(4S6S)β; and CS-AA, GlcAβ-GalNAc(4S)β-GlcAβ-GalNAc(4S)β, having biotin linked with a hydrophilic linker at the reducing terminal were synthesized effe...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2012-02, Vol.22 (3), p.1371-1374
Main Authors: Tamura, Jun-ichi, Tsutsumishita-Nakai, Nao, Nakao, Yasuhiro, Kawano, Manami, Kato, Saki, Takeda, Naoko, Nadanaka, Satomi, Kitagawa, Hiroshi
Format: Article
Language:English
Subjects:
Biological and medical sciences
Biotin
Biotinylation
Carbohydrate Sequence
Chondroitin sulfate
Chondroitin Sulfates - chemical synthesis
Chondroitin Sulfates - chemistry
Cytokines - chemistry
Disaccharides
Glycosaminoglycan
hydrophilicity
Medical sciences
Midkine
Molecular Sequence Data
Oligosaccharides - chemical synthesis
Oligosaccharides - chemistry
Pharmacology. Drug treatments
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Summary:Regiospecifically sulfated chondroitin sulfate repeating tetrasaccharides, CS-OO, GlcAβ-GalNAcβ-GlcAβ-GalNAcβ; CS-EE, GlcAβ-GalNAc(4S6S)β-GlcAβ-GalNAc(4S6S)β; and CS-AA, GlcAβ-GalNAc(4S)β-GlcAβ-GalNAc(4S)β, having biotin linked with a hydrophilic linker at the reducing terminal were synthesized effectively by a coupling of the corresponding disaccharide units and regioselective sulfation. CS-EE showed greater affinity for midkine than CS-AA and CS-OO. Regiospecifically sulfated chondroitin sulfate repeating tetrasaccharides, CS-OO, GlcAβ-GalNAcβ-GlcAβ-GalNAcβ;CS-EE, GlcAβ-GalNAc(4S6S)β-GlcAβ-GalNAc(4S6S)β; and CS-AA, GlcAβ-GalNAc(4S)β-GlcAβ-GalNAc(4S)β, having biotin linked with a hydrophilic linker at the reducing terminal were synthesized effectively by a coupling of the corresponding disaccharide units and regioselective sulfation. CS-EE showed greater affinity for midkine than CS-AA and CS-OO.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2011.12.054