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

Atsushi Hara; Akihiro Imamura; Hiromune Ando; Hideharu Ishida; Makoto Kiso

doi:10.3390/molecules19010414

Molecules (Dec 2013)

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

Atsushi Hara,
Akihiro Imamura,
Hiromune Ando,
Hideharu Ishida,
Makoto Kiso

Affiliations

Atsushi Hara: Department of Applied Bioorganic Chemistry, Faculty of Applied Biological Sciences, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan
Akihiro Imamura: Department of Applied Bioorganic Chemistry, Faculty of Applied Biological Sciences, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan
Hiromune Ando: Department of Applied Bioorganic Chemistry, Faculty of Applied Biological Sciences, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan
Hideharu Ishida: Department of Applied Bioorganic Chemistry, Faculty of Applied Biological Sciences, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan
Makoto Kiso: Department of Applied Bioorganic Chemistry, Faculty of Applied Biological Sciences, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan

DOI: https://doi.org/10.3390/molecules19010414
Journal volume & issue: Vol. 19, no. 1
pp. 414 – 437

Abstract

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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.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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