Methods of synthesizing GM3

Details Methods of synthesizing GM3 Methods of synthesizing GM3

1998-02-17

1999-11-02

Fonda, Kathleen K.

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

Organic compounds

Carbohydrates or derivatives

536 185, C07H 1500

Patent

active

059773294

ABSTRACT:
The invention describes an improved method for making monosialoganglioside GM3 and its intermediates. Following reaction of a neuraminic acid donor and a lactose acceptor in the presence of an acid catalyst, the .alpha. and .beta. isomers of GM3 are formed. The .alpha. isomer is converted to a lactone, via action of a ring forming basic catalyst, which is then separable from the .beta. isomer. The lactone is then treated with a basic catalyst in the presence of an alcohol, to form GM3 or a GM3 intermediate.

REFERENCES:
patent: 4593091 (1986-06-01), della Valle et al.
patent: 5756695 (1998-05-01), Schmidt et al.
Sugimoto et al. Carbohydr. Res. 1986, 156, C1-C5. Month not available.
Hasegawa et al., "Synthetic Studies on Sialoglycoconjugates 41: A Facile Total Synthesis of Ganglioside GM.sub.2, " J. Carbohydrate Chem. 11(6):669-714, 1992 (month not available).
Schmidt, "Chemical Synthetis of Sialylated Glycoconjugates in Synthetic Oligosaccharides: Indispensable Probes for the Life Sciences," (ACS Syposium Genes, 560, 1994) (month not available).
Martin et al., "Synthesis of Phosphites and Phosphates of Neuraminic Acid and Their Glycosyl Donor Properties--Convenient Synthesis of GM.sub.2," Glycoconjugate Journal, 10:16-25 (1993) (month not available).

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