Synthesis of 9-0-acetyl N-acetylneuraminic acid oligosaccharides

Details Synthesis of 9-0-acetyl N-acetylneuraminic acid oligosaccharides Synthesis of 9-0-acetyl N-acetylneuraminic acid oligosaccharides

1996-08-26

1998-06-16

Lilling, Herbert J.

Chemistry: molecular biology and microbiology

Micro-organism, tissue cell culture or enzyme using process...

Preparing compound containing saccharide radical

435 84, 435200, 435201, 536 41, 536 172, 536 179, C12P 1944, C12P 1926, C12N 924

Patent

active

057668876

ABSTRACT:
Regioselective acetylation of the 9-hydroxyl group on N-acetylneuraminic acid is achieved enzymatically for producing oligosaccharides which contain a terminal N-acetylneuraminic acid moiety. This method provides access to O-acylated disialogangliosides as well as other N-acetyl-neuraminic acid oligosaccharides. These compounds are biologically and medicinally important and are difficult to obtain from nature or by chemical acylations. The methodology affords simple reaction conditions and minimal purification steps. In addition, the process affords good yields and the enzymes and reagents employed are commercially available with high stability and low costs.

REFERENCES:
patent: 5461143 (1995-10-01), Wong
Ritter, et al., "Biochemical and Serological Characteristics of Natural 9-0-Acetyl GD3 from Human Melanoma and Bovine Buttermilk and Chemically 0-Acetylated GD3", Cancer Research, 50:1403-1410 (1990).

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