Process for preparing nucleotide inhibitors of glycosyltransfera

Details Process for preparing nucleotide inhibitors of glycosyltransfera Process for preparing nucleotide inhibitors of glycosyltransfera

1996-12-10

1998-06-23

Kunz, Gary L.

Chemistry: molecular biology and microbiology

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

Preparing compound containing saccharide radical

435 15, 536 553, C12Q 148, C12P 1930, C07H 100

Patent

active

057704074

ABSTRACT:
Nucleotide linked 2-deoxy-2-fluoroglycosides are employed as potent competitive inhibitors of glycosyltransferases. More particularly, uridine-5'-diphospho-2-deoxy-2-fluoro-galactose (UDP-2F-Gal), guanidine-5'-diphospho-2-deoxy-2-fluoro-L-fucose (GDP-2F-Fuc), uridine-51-diphospho-2-deoxy-2-fluoro-D-glucose (UDP-2F-Glu), guanosine-5'-diphospho-2-deoxy-2-fluoro-D-mannose (GDP-2F-Man), cytosine-5'-monophospho-2-deoxy-2-fluoro-D-sialic acid, and cytosine-5'-monophospho-2-deoxy-2-KDO may be employed as inhibitors of .beta.-1,4-galactosyltransferase, .alpha.-1,3-fucosyltransferase, glucosyltransferases, N-acetylglucosaminyltransferases, (.alpha.-mannosyltransferases, .alpha.-sialyltransferases, and KDO-transferases, respectively. Synthesis of nucleotide-linked-2-deoxy-2-fluoroglycosides is achieved using either chemoenzymatic or chemical methodologies.

REFERENCES:
Withers, et al., "2-Deoxy-2-fluoro-D-glycosyl Fluorides", J. Biol. Chem., 263:7929-7932 (1988).
McCarter, et al., "5-Fluor Glycosides: A New Class of Mechanism-Based . . . ", J. Am. Chem. Soc., 118:241-242 (1996).
Qiao, et al., "Synergistic Inhibition of Human . . . ", J. Am. Chem. Soc., 118:7653-7662 (1996).
Murray, et al., "Mechanism and Specificity of Human . . . ", Biochemistry, 35:11183-11195 (1996).
Sinnott, Michael, "Catalytic Mechanisms of Enzymic Glycosyl Transfer", Chem. Rev., 90:1171-1202 (1990).
White, et al., "Crystallographic Observation of a Covalent Catalytic . . . ", Nature Structural Biology, 3:149-154 (1996).
Withers, et al., "Identification of a Covalent alpha-D-. . . ", J. Am. Chem. Soc., 110:8551-8553 (1988).
Withers, et al., "Unequivocal Demonstrations of the Involvement of a . . . ", J. Am. Chem. Soc., 112:5887-5889 (1990).
Ichikawa, et al., "Chemical-Enzymatic Synthesis and Conformational . . . ", J. Am. Chem. Soc., 114:9283-9298 (1992).
Adelhorst, et al., "Large-Scale Synthesis of Beta-L-fucopyranosyl . . . ", Carbohydrate Research, 242:69-76 (1993).
Gokhase, et al., "Chemical Synthesis of GDP-Fucose . . . ", Can. J. Chem., 68:1063-1071 (1990).
Veeneman, et al., "An Approach towards the synthesis of 1,2-trans . . . ", Tetrahedron Letters, 43:6175-6178 (1991).
Moffatt, J.G., "Sugar Nucleotide Synthesis . . . ", Meth. Enzymol., 8:136-142 (1966).
Roseman, et al., "Nucleoside Polyphosphates . . . ", J. Am. Chem. Soc., 83:659-663 (1961).
Heidlas, et al., "Nucleoside Phosphate Sugars: Syntheses . . . ", Acc. Chem. Res., 25:307-314 (1992).
Kochetkov, et al., "Glycosyl Esters of Nucleoside Pyrophosphates", Adv. Carbo. Chem. Biochem., 28:307-399 (1973).
Hoard, et al., "Conversion of Mono- andOligodeoxyribonucleotides . . . ", J. Am. Chem. Soc., 87:1785-1788 (1965).
Simon, et al., "Convenient Syntheses . . . ", J. Org. Chem., 55:1834-1841 (1990).
Moffatt, et al., "The Total Synthesis of Coenzyme A", J. Am. Chem. Soc., 81:1265 (1959).
Moffatt, et al., "Nucleoside Pholyphosphates . . . ", J. Am. Chem. Soc., 83:649-658 (1961).
Wong, et al., "Enzyme-Catalyzed Synthesis of N-Acetyllactosamine . . . ", J. Org. Chem., 47:5416-5418 (1982).
Stiller, et al., "Enzymatic Synthesis of Beta-L-Fucose-1-phosphate . . . ", Liebigs Ann. Chem., 467-471 (1992).

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