Synthesis of an Aminooxy Derivative of the Trisaccharide Globotriose Gb3.
The synthesis of α-aminooxy trisaccharide moiety [α-d-Gal-(1,4)-β-d-Gal-(1,4)-β-d-Glc-α-aminooxy], related to the cell surface globotriaosylceramide (Gb3) receptor of the B subunit of the AB5Shiga toxin ofShigella dysenteriae, has been synthesized for the first time in 11 steps with a 15% overall isolated yield. A highlight of this work entails utilizing chemically compatible synthetic transformations, including those related to glycosylation, incorporative of the succinimidyl moiety as a precursor to the aminooxy Gb3 derivative. The fully deprotected trisaccharide aminooxy compound was reacted with a carbonyl compound leading to oxime formation in quantitative yield underscoring the importance for future glyco-conjugations.
Department of Chemistry and Biochemistry and School of Green Chemistry and Engineering, The University of Toledo, 2801 W. Bancroft St, Toledo, OH 43606.
Samir
S
Ghosh
Department of Chemistry and Biochemistry and School of Green Chemistry and Engineering, The University of Toledo, 2801 W. Bancroft St, Toledo, OH 43606.
Peter R
PR
Andreana
Gb3 trisaccharide; Shiga toxin; aminooxy sugar; glycosylation