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Molecules 2014, 19(1), 414-437; doi:10.3390/molecules19010414

A New Chemical Approach to Human ABO Histo-Blood Group Type 2 Antigens

1,* , 1,2
1 Department of Applied Bioorganic Chemistry, Faculty of Applied Biological Sciences, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan 2 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 / Revised: 24 December 2013 / Accepted: 25 December 2013 / Published: 31 December 2013
(This article belongs to the Special Issue Oligosaccharides and Glyco-Conjugates)
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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 blood group antigen; oligosaccharide; glycosylation; Heyns rearrangement
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

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