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.
Highlights
ABO histo-blood group antigens are expressed on red blood cells and are widely distributed in various tissues such as the vascular endothelium, where they are displayed on plasmalemmal glycoproteins and glycolipids by attachment to sugar residues that terminate N-linked, O-linked, and lipid-linked glycans [1,2]
2)]Gal, Galα(1-3)[Fucα(1-2)]Gal, and Fucα(1-2)Gal glycan structures, respectively. These antigens can be further divided into six subtypes based on linkage arrangement: type 1, ABO-β(1-3)GlcNAcβ; type 2, ABO-β(1-4)GlcNAcβ; type 3, ABO-β(1-4)GalNAcα; type 4, ABO-β(1-3)GalNAcβ; type 5, ABO-β(1-3)Galβ; and type 6: ABO-β(1-4)Glcβ [3,4]
We have developed a novel approach to synthesizing human histo-blood group type 2 antigens
Summary
ABO histo-blood group antigens are expressed on red blood cells and are widely distributed in various tissues such as the vascular endothelium, where they are displayed on plasmalemmal glycoproteins and glycolipids by attachment to sugar residues that terminate N-linked, O-linked, and lipid-linked glycans [1,2]. 2)]Gal, Galα(1-3)[Fucα(1-2)]Gal, and Fucα(1-2)Gal glycan structures, respectively. These antigens can be further divided into six subtypes based on linkage arrangement: type 1, ABO-β(1-3)GlcNAcβ; type 2, ABO-β(1-4)GlcNAcβ; type 3, ABO-β(1-4)GalNAcα; type 4, ABO-β(1-3)GalNAcβ; type 5, ABO-β(1-3)Galβ; and type 6: ABO-β(1-4)Glcβ [3,4]. We envisioned that chemically synthesized pure samples would enable a range of studies on the physiological and pathological implications of ABO group antigens. The goal of our research is to develop a facile synthetic route to ABO histo-blood group antigens, type 2 glycans. We describe a new chemical approach to ABO group type 2 antigens with a pentylamine linker (1‒3; Figure 1), which are expected to be useful in future biological studies
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