ISSN:
1434-193X
Keywords:
Glycosyl phosphates
;
Nucleosidephosphate sugars
;
Neuraminic acid
;
Glycosyltransferase
;
Carbohydrates
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
---The reaction of sialyl phosphites 1, 22a-d, 28, 39, and 45 with acyl-protected riboside 5-phosphorous acids 2a,b and 23 directly furnished, without addition of a catalyst, under phosphite/phosphate exchange the corresponding β-configured sialyl riboside monophosphates 3a,b, 24a-d, 29, 46, and 47. The synthesis of the starting materials, formation of the products, and their treatment with sodium methanolate in methanol and subsequent hydrolysis of the sialic acid ester moiety to provide the unprotected target molecules 4a,b, 25a-d, 30, 48, and 49 is described. Investigations with α(2-6)-sialyltransferase from rat liver showed that base replacement in CMP-Neu5Ac (4a,b) is not tolerated by the enzyme but that modifications of the 5-, 8-, or 9-position of the neuraminic acid residue (25a-d, 30, 48, 49) are tolerated.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
