Synthesis of mono- and di-α-l-fucosylated 2-acetamido-2-deoxy-N-glycyl-β-d-glucopyranosylamines, spacered fragments of glycans of N-glycoproteins

α- l -Fuc p -(1→3)- d -GlcNAc, α- l -Fuc p -(1→6)-[α- l -Fuc p -(1→3)]- d -GlcNAc, and β- d -Gal p -(1→3)-[α- l -Fuc p -(1→4)]- d -GlcNAc were converted into corresponding β-glycopyranosylamines by action of ammonium carbamate in aqueous boric acid, or in aqueous methanol in case of α- l -Fuc p -(1→...

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Published in:	Russian chemical bulletin Vol. 64; no. 5; pp. 1134 - 1141
Main Authors:	Likhosherstov, L. M., Novikova, O. S., Malysheva, N. N., Piskarev, V. E.
Format:	Journal Article
Language:	English
Published:	New York Springer US 01-05-2015
Subjects:	Chemistry Chemistry and Materials Science Chemistry/Food Science Full Articles Inorganic Chemistry Organic Chemistry fucose carbohydrate-peptide bond α 2-acetamido-2-deoxy-β oligosaccharides glycoproteins glucopyranose glycyl-β-glucopyranosylamines acylation
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Summary:	α- l -Fuc p -(1→3)- d -GlcNAc, α- l -Fuc p -(1→6)-[α- l -Fuc p -(1→3)]- d -GlcNAc, and β- d -Gal p -(1→3)-[α- l -Fuc p -(1→4)]- d -GlcNAc were converted into corresponding β-glycopyranosylamines by action of ammonium carbamate in aqueous boric acid, or in aqueous methanol in case of α- l -Fuc p -(1→6)- d -GlcNAc. N -Acylation of these fucooligosaccharides with N -Z-glycine N -hydroxysuccinimide ester (Z is benzyloxycarbonyl) followed by hydrogenolytic removal of Z-group afforded corresponding N -glycyl-β-glycopyranosylamines of these fucooligosaccharides; three of them model carbohydrate-peptide region of N -glycoproteins, and the forth is an amino-spacered Le a -antigen.
ISSN:	1066-5285 1573-9171
DOI:	10.1007/s11172-015-0990-7