The Synthesis of Blood Group Antigenic A Trisaccharide and Its Biotinylated Derivative.

Ekaterina D Kazakova,Nikolay E Nifantiev,Dmitry V Yashunsky

doi:10.3390/molecules26195887

Ekaterina D Kazakova, Nikolay E Nifantiev + Show 1 more

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https://doi.org/10.3390/molecules26195887

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Abstract

Blood group antigenic A trisaccharide represents the terminal residue of all A blood group antigens and plays a key role in blood cell recognition and blood group compatibility. Herein, we describe the synthesis of the spacered A trisaccharide by means of an assembly scheme that employs in its most complex step the recently proposed glycosyl donor of the 2-azido-2-deoxy-selenogalactoside type, bearing stereocontrolling 3-O-benzoyl and 4,6-O-(di-tert-butylsilylene)-protecting groups. Its application provided efficient and stereoselective formation of the required α-glycosylation product, which was then deprotected and subjected to spacer biotinylation to give both target products, which are in demand for biochemical studies.

Highlights

Besides playing an important role in blood cell recognition and blood group compatibility, blood transfusion, and organ transplantation [11,12,13], A trisaccharide and structurally related compounds can be used as haptens to test the carbohydrate specificities of plant [14]
A trisaccharide represents the minimal terminal fragment of all blood group A antigens. It has a branched structure where the central β-Gal residue is glycosylated with α-fucose at O-2 and with α-galactosamine at O-3
Despite numerous works devoted to the synthesis of oligosaccharides related to blood group antigens, there are only a few papers dedicated to the synthesis of A trisaccharide derivatives [4,5,6,9]

Summary

Introduction

Since the discovery of the ABO blood group system and the role of carbohydrate residues in blood antigens [1,2], there has been continued interest in developing new synthetic approaches to the assembly of carbohydrate blood group antigen determinants [3,4,5,6,7,8,9,10]. Mammalian lectins [15,16] and serve as a model for conformational and spectral studies [17] of vicinally branched oligosaccharides. A trisaccharide derivatives can serve as model compounds in the development of new biomedical technologies, since antibodies against this carbohydrate antigen are commercially available. A trisaccharide represents the minimal terminal fragment of all blood group A antigens It has a branched structure where the central β-Gal residue is glycosylated with α-fucose at O-2 and with α-galactosamine at O-3 (see Figure 1). Despite numerous works devoted to the synthesis of oligosaccharides related to blood group antigens, there are only a few papers dedicated to the synthesis of A trisaccharide derivatives [4,5,6,9]. The studies discussed below were planned to fill these gaps

Results and Discussion

General Information

Conclusions