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Abstract
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.
Graphical Abstract
Four types of biotinylated keratan sulfate repeating disaccharides containing non-sulfate were synthesized in an efficient and stereo-controlled manner.
Acknowledgments
This study was supported by grant aid for scientific research in innovative areas (23110003) from MEXT, Japan. N.T. is grateful for the JSPS Research Fellowship for Young Scientists. We thank Mrs. Mayumi Ikenari (Research Center for Bioscience and Technology, Division of Instrumental Analysis, Tottori University) for performing the ESI-HRMS measurements.
Notes
Abbreviations: KS, keratan sulfate; NAP, 2-naphthylmethyl; TBDPS, tert-butyldiphenylsilyl; TMSOTf, trimethylsilyl trifluoromethanesulfonate; MBz, 4-methylbenzoyl; Z, benzyloxycarbonyl; Bn, benzyl; NIS, N-iodosuccinimide; TfOH, trifluoromethanesulfonic acid; DDQ, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; Phth, phthaloyl; DMAP; dimethylaminopyridine; THF, tetrahydrofurane; MS4A, molecular sieves 4A.