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[21] Preparation of cytidine 5′-monophospho-N-acetylneuraminic acid and uridine 5′-diphosphoglucuronic acid; syntheses of α-2, 6-sialyllactosamine, α-2, 6-sialyllactose, and hyaluronic acid

1989; Academic Press; Linguagem: Inglês

10.1016/0076-6879(89)79129-1

1557-7988

by Ethan S. Simon, Eric J. Toone, Gary R. Ostroff, Mark D. Bednarski, George M. Whitesides,

Carbohydrate Chemistry and Synthesis

This chapter describes the preparation of two representative nucleoside phosphate sugars, cytidine 5'-monophospho- N-acetylneuraminic acid (CMPNeuAc) and uridine 5'-diphosphoglucuronic acid 5 (UDPGlcUA). Both compounds are useful for the in vitro synthesis of complex oligosaccharides. This chapter also presents a mulfigram synthesis for CMPNeuAc involving both chemical and enzymatic transformations, and it illustrates the use of the isolated material by the syntheses of α-2, 6-sialyllactosamine and α-2, 6-sialyllactose using glycosyltransferases. An enzymatic preparation of UDPGlcUA has been developed using UDPglucose dehydrogenase. Although product inhibition prevents the isolation of product, UDPGlcUA produced in situ by this method can be efficiently incorporated into the important biological polymer hyaluronic acid.