Synthesis of 3-O-sulfoglucuronyl lacto-N-neotetraose 2-aminoethyl glycoside and biotinylated neoglycoconjugates thereof.
The 2-aminoethyl glycoside of pentasaccharide 3-O-sulfo-GlcA(beta-1-->3)Gal(beta-1-->4)GlcNAc(beta-1-->3)Gal(beta-1--> 4)Glc(beta (1) and its conjugates with biotin and biotinylated polyacrylic acid were synthesized as molecular probes to investigate the recognition of the HNK-1 epitope containing carbohydrates by proteins. Key steps in the first of two investigated schemes for the preparation of the target compound 1 were (a) assembling of the pentasaccharide backbone (compound 10) by glycosylation of selectively substituted allyl glycoside of the trisaccharide GlcNAc(beta-1-->3)Gal(beta-1-->4)Glc(beta with glucuronyl-galactose glycosyl donor, (b) transformation of the allyl aglycon in 10 into 2-azidoethyl one (to give 11), (c) selective deprotection of the OH group at C-3 of the GlcA residue in 11 via saponification, intramolecular formation of 6,3-lacton (13) and its methanolysis, and (d) subsequent O-sulfation. The alternative scheme with the use of 2-azido-ethyl glycoside of the trisaccharide GlcNAc(beta-1-->3)Gal(beta-1-->4)Glc(beta instead of the allyl glycoside 6 was less effective due to smaller yield at the step of pentasaccharide synthesis. Additionally to 1 the 2-aminoethyl glycosides of the oligosaccharides GlcA(beta-1-->3)Gal(beta-1-->4)GlcNAc(beta-1-->3)Gal(beta-1-->4)Glc(beta, 3-O-sulfo-GlcA(beta-1-->3)Gal(beta, and GlcA(beta-1-->3)Gal(beta were also synthesized.
Kornilov
A V
AV
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow.
Sherman
A A
AA
Kononov
L O
LO
Shashkov
A S
AS
Nifant'ev
N E
NE
D000180:Acrylic Resins / Q000737:chemistry*; D000818:Animals; D001710:Biotin / Q000737:chemistry; D019921:Biotinylation; D018959:CD57 Antigens / Q000737:chemistry; D002240:Carbohydrate Sequence; D000939:Epitopes; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry / Q000276:immunology; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000276:immunology; D009682:Magnetic Resonance Spectroscopy; D015335:Molecular Probes / Q000138:chemical synthesis / Q000276:immunology; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000276:immunology; D019087:Selectins / Q000378:metabolism
C421630:2-aminoethyl (3-O-sulfoglucopyranosyluronic acid)-1-3-galactopyranosyl-1-4-(2-acetamido-2-deoxyglucopyranosyl)-1-3-galactopyranosyl-1-4-glucopyranoside; D000180:Acrylic Resins; D018959:CD57 Antigens; D000939:Epitopes; D006001:Glycoconjugates; D006027:Glycosides; D015335:Molecular Probes; D009844:Oligosaccharides; D019087:Selectins; C006903:carbopol 940; D001710:Biotin