Method for producing synthetic N-linked glycoconjugates

Details Method for producing synthetic N-linked glycoconjugates Method for producing synthetic N-linked glycoconjugates

1995-06-30

1997-09-16

Kight, John

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 552, 530322, C07H 504, C07H 506, C07K 900

Patent

active

056682727

ABSTRACT:
A transamination reaction of glycosyl-1-amine with a nucleophilic reagent containing an --NH.sub.2 or --NHNH.sub.2 group is used to prepared a broad spectrum of glycoconjugates by substitution of the 1-amino group. The substitution reaction does not adversely affect the ring structure of the sugar as does the prior art reductive amination reaction. Suitable nucleophilic reagents are nucleophiles having a chromophore group, a fluorophore group, a chemiluminescent group, a lipid, an amino acid or peptide moiety, biotin, a drug and a linker/spacer group and an affinity label. The ratio of glycosyl-1-amine to nucleophilic reagent is in the range of from about 1:1 to about 1:2 by weight.

REFERENCES:
patent: 5019231 (1991-05-01), Bradley et al.
patent: 5212298 (1993-05-01), Rademacher et al.
patent: 5280113 (1994-01-01), Rademacher et al.
Int. J. Peptide Res., vol. 39, Issued 1992, L. Varga-Defferdarovic, "Glycoconjugates of Opioid Peptides", pp. 12-17.
Bioconjugate Chem., vol. 6, 1995, pp. 316-318, D. Vetter and M.A. Gallop: "Strategies for the Synthesis and Screening of Glycoconjugates".
J. Org. Chem., vol. 23, 1958, pp. 1309-1319, H.S. Isbell and H.L. Frush: "Mutarotation, Hydrolysis, and Rearrangement Reactions of Glycosylamines".
Carbohydr. Res., vol. 149, 1986. pp. 329-345, A. Gomez-Sanchez et al: "Synthesis and Glycosidation of 1-Deoxy-1-((2,2-Diacylvinyl)amino)-D-Fructoses".

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