We successfully synthesized the biotinylated keratan sulfate tetrasaccharide, Galβ1-4GlcNAc6Sβ1-3Galβ1-4GlcNAc6Sβ in a stereocontrolled manner. The suitably protected Galβ1-4GlcNPhth unit was converted to the corresponding donor and acceptor. Optimization in 2 + 2 coupling using AgOTf, CuBr, and n-BuNBr in CHNO at a low temperature afforded the desired tetrasaccharide that suppressed glycal formation. The subsequent chemoselective removal of the protecting group at O-6 of two GlcNAcs, sulfation, and deprotection procedures as well as biotinylation gave the target compound.
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Synthesis of a biotinylated keratan sulfate tetrasaccharide composed of dimeric Galβ1-4GlcNAc6Sβ.
Carbohydr Res
November 2017
Department of Regional Environment, Faculty of Regional Sciences, Tottori University, Tottori 680-8551, Japan; Department of Life and Environmental Agricultural Sciences, Faculty of Agriculture, Tottori University, Tottori 680-8553, Japan. Electronic address:
We successfully synthesized the biotinylated keratan sulfate tetrasaccharide, Galβ1-4GlcNAc6Sβ1-3Galβ1-4GlcNAc6Sβ in a stereocontrolled manner. The suitably protected Galβ1-4GlcNPhth unit was converted to the corresponding donor and acceptor. Optimization in 2 + 2 coupling using AgOTf, CuBr, and n-BuNBr in CHNO at a low temperature afforded the desired tetrasaccharide that suppressed glycal formation.
View Article and Find Full Text PDFBinding specificity of R-10G and TRA-1-60/81, and substrate specificity of keratanase II studied with chemically synthesized oligosaccharides.
Glycoconj J
December 2017
Research Center for Glycobiotechnology, Ritsumeikan University, Noji-Higashi, 1-1-1, Kusatsu, Shiga, 525-8577, Japan.
Recently, we established a mouse monoclonal antibody specific to hiPS/ hES cells, R-10G, which recognizes a type of keratan sulfate. Keratan sulfates (KS) comprise a family of glycosaminoglycans consisting of the repeating unit of [Gal-GlcNAc(6S)]. However, there is a diversity in the degree of sulfation at Gal and GlcNAc residues, and also in the mode of linkage, Galβ1 - 3GlcNAc (type 1) or Galβ1 - 4GlcNAc (type 2).
View Article and Find Full Text PDFSynthesis of biotinylated keratan sulfate repeating disaccharides.
Biosci Biotechnol Biochem
March 2015
a Department of Chemistry and Biotechnology, Graduate School of Engineering , Tottori University, Tottori , Japan.
We synthesized four types of keratan and keratan sulfate repeating disaccharides containing non-sulfate, Galβ1-4GlcNAcβ, and three types of sulfates, Gal6Sβ1-4GlcNAcβ, Galβ1-4GlcNAc6Sβ, and Gal6Sβ1-4GlcNAc6Sβ in an efficient and stereo-controlled manner. These disaccharides were conjugated with biotin via a hydrophilic linker at the reducing terminal.
View Article and Find Full Text PDFHeparin affects the interaction of kininogen on endothelial cells.
Biochimie
October 2011
Department of Biochemistry, Universidade Federal de São Paulo, 04044-020 SP, Brazil.
In the plasma kallikrein-kinin system, it has been shown that when plasma prekallikrein (PK) and high molecular weight kininogen (HK) assemble on endothelial cells, plasma kallikrein (huPK) becomes available to cleave HK, releasing bradykinin, a potent mediator of the inflammatory response. Because the formation of soluble glycosaminoglycans occurs concomitantly during the inflammatory processes, the effect of these polysaccharides on the interaction of HK on the cell surface or extracellular matrix (ECM) of two endothelial cell lines (ECV304 and RAEC) was investigated. In the presence of Zn(+2), HK binding to the surface or ECM of RAEC was abolished by heparin; reduced by heparan sulfate, keratan sulfate, chondroitin 4-sulfate or dermatan sulfate; and not affected by chondroitin 6-sulfate.
View Article and Find Full Text PDFPURPOSE. To map the distribution of different classes of glycosaminoglycans (GAGs) in the healthy human retina, choroid, and sclera. METHODS.
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