Synthesis of a cyclic tetramer of 3-amino-3-deoxyallose with axially oriented amino groups

Olga N Yudina; Marina L Gening; Pinaki Talukdar; Alexey G Gerbst; Yury E Tsvetkov; Nikolay E Nifantiev

doi:10.1016/j.carres.2021.108476

Synthesis of a cyclic tetramer of 3-amino-3-deoxyallose with axially oriented amino groups

Carbohydr Res. 2022 Jan:511:108476. doi: 10.1016/j.carres.2021.108476. Epub 2021 Nov 10.

Authors

Olga N Yudina¹, Marina L Gening¹, Pinaki Talukdar², Alexey G Gerbst¹, Yury E Tsvetkov¹, Nikolay E Nifantiev³

Affiliations

¹ Laboratory of Glycoconjugate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp, 119991, Moscow, Russian Federation.
² Department of Chemistry, Indian Institute of Science Education and Research Pune, Dr. Homi Bhabha Road, Pashan, Pune, 411008, Maharashtra, India.
³ Laboratory of Glycoconjugate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp, 119991, Moscow, Russian Federation. Electronic address: [email protected].

PMID: 34800752
DOI: 10.1016/j.carres.2021.108476

Abstract

A linear tetramer of β-(1 → 6)-linked 3-azido-3-deoxy-d-allose containing glycosyl donor and glycosyl acceptor functions in the terminal monosaccharide units was prepared starting from 3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-d-allofuranose. Cyclization of the linear tetramer under glycosylation conditions afforded the corresponding cyclic tetrasaccharide in 77% yield; its deprotection and reduction of the azido groups resulted in the formation of the cyclic tetramer of 3-amino-3-deoxy-d-allose with axial amino groups, a potential scaffold for the synthesis of tetravalent functional clusters.

Keywords: 3-Amino-3-deoxy-d-allose; Axial amino group; Cyclic oligosaccharides; Cyclic tetrasaccharide; Synthesis.

MeSH terms

Glycosylation
Oligosaccharides*

Substances

Oligosaccharides