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A New Chemical Approach to Human ABO Histo-Blood Group Type 2 Antigens
Department of Applied Bioorganic Chemistry, Faculty of Applied Biological Sciences, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan
Institute for Integrated Cell-Material Sciences (WPI-iCeMS), Kyoto University, Yoshida Ushinomiya-cho, Sakyo-ku, Kyoto 606-8501, Japan
* Author to whom correspondence should be addressed.
Received: 13 December 2013; in revised form: 24 December 2013 / Accepted: 25 December 2013 / Published: 31 December 2013
Abstract: A new chemical approach to synthesizing human ABO histo-blood type 2 antigenic determinants was developed. N-Phthaloyl-protected lactosaminyl thioglycoside derived from lactulose via the Heyns rearrangement was employed to obtain a type 2 core disaccharide. Use of this scheme lowered the overall number of reaction steps. Stereoselective construction of the α-galactosaminide/galactoside found in A- and B-antigens, respectively, was achieved by using a unique di-tert-butylsilylene-directed α-glycosylation method. The proposed synthetic scheme provides an alternative to existing procedures for preparing ABO blood group antigens.
Keywords: blood group antigen; oligosaccharide; glycosylation; Heyns rearrangement
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Hara, A.; Imamura, A.; Ando, H.; Ishida, H.; Kiso, M. A New Chemical Approach to Human ABO Histo-Blood Group Type 2 Antigens. Molecules 2014, 19, 414-437.
Hara A, Imamura A, Ando H, Ishida H, Kiso M. A New Chemical Approach to Human ABO Histo-Blood Group Type 2 Antigens. Molecules. 2014; 19(1):414-437.
Hara, Atsushi; Imamura, Akihiro; Ando, Hiromune; Ishida, Hideharu; Kiso, Makoto. 2014. "A New Chemical Approach to Human ABO Histo-Blood Group Type 2 Antigens." Molecules 19, no. 1: 414-437.