Chemo-enzymatic synthesis of fluorinated 2-N-acetamidosugar nucleotides using UDP-GlcNAc pyrophosphorylase

被引:24
作者
Feng, F
Okuyama, K
Niikura, K
Ohta, T
Sadamoto, R
Monde, K
Noguchi, T
Nishimura, SI [1 ]
机构
[1] Hokkaido Univ, Grad Sch Sci, Div Biol Sci, Lab Biomacromol Chem, Sapporo, Hokkaido 0010021, Japan
[2] YAMASA Corp, Div Biochem, Bioprod Lab, Chiba 2880056, Japan
[3] Natl Inst Adv Ind Sci & Technol, Sapporo, Hokkaido 0628517, Japan
[4] Hokkaido Univ, Grad Sch Sci, Div Biol Sci, Shionogi Lab Biomol Chem, Sapporo, Hokkaido 0010021, Japan
关键词
D O I
10.1039/b402860k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two non-natural. uorinated 2-N-acetamidosugar nucleotides, uridine 5'-diphosphate (UDP) 2-acetamido-2,4-dideoxy-4-fluoro-alpha-D-glucopyranose (UDP-4-FGlcNAc) 1 and its galacto isomer (UDP-4-FGalNAc) 2, were enzymatically constructed by treating chemically synthesized. uorinated 2-N-acetamidosugar 1-phosphates as the donor with UDP 2-acetamido-2-deoxy-alpha-D-glucopyranose pyrophosphorylase in the presence of uridine 5'-triphosphate (UTP).
引用
收藏
页码:1617 / 1623
页数:7
相关论文
共 27 条
[1]   Synthesis of 4-deoxy-4-fluoro analogues of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-galactose and their effects on cellular glycosaminoglycan biosynthesis [J].
Berkin, A ;
Szarek, WA ;
Kisilevsky, R .
CARBOHYDRATE RESEARCH, 2000, 326 (04) :250-263
[2]   Chemo-enzymatic synthesis of fluorinated sugar nucleotide:: Useful mechanistic probes for glycosyltransferases [J].
Burkart, MD ;
Vincent, SP ;
Düffels, A ;
Murray, BW ;
Ley, SV ;
Wong, CH .
BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (08) :1937-1946
[3]  
BURTON A, 1997, J CHEM SOC P1, V16, P2375
[4]   SYNTHESIS OF UDP-4-DEOXY-4-FLUOROGLUCOSE AND UDP-4-DEOXY-4-FLUOROGALACTOSE AND THEIR INTERACTIONS WITH ENZYMES OF NUCLEOTIDE SUGAR METABOLISM [J].
CHAPEAU, MC ;
FREY, PA .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (23) :6994-6998
[5]   BETA-1-6 BRANCHING OF ASN-LINKED OLIGOSACCHARIDES IS DIRECTLY ASSOCIATED WITH METASTASIS [J].
DENNIS, JW ;
LAFERTE, S ;
WAGHORNE, C ;
BREITMAN, ML ;
KERBEL, RS .
SCIENCE, 1987, 236 (4801) :582-585
[6]   A NOVEL, REDUCTIVE RING-OPENING OF CARBOHYDRATE BENZYLIDENE ACETALS, WITH UNUSUAL REGIOSELECTIVITY [J].
GAREGG, PJ ;
HULTBERG, H .
CARBOHYDRATE RESEARCH, 1981, 93 (01) :C10-C11
[7]  
GRIER TJ, 1984, J BIOL CHEM, V259, P1027
[8]   Synthesis of 5-fluoro N-acetylglucosamine glycosides and pyrophosphates via epoxide fluoridolysis:: Versatile reagents for the study of glycoconjugate biochemistry [J].
Hartman, MCT ;
Coward, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (34) :10036-10053
[9]   A chemoenzymatic synthesis of UDP-(2-deoxy-2-fluoro)galactose and evaluation of its interaction with galactosyltransferase [J].
Hayashi, T ;
Murray, BW ;
Wang, R ;
Wong, CH .
BIOORGANIC & MEDICINAL CHEMISTRY, 1997, 5 (03) :497-500
[10]   Substituent effects of the C6-position on ring-opening polymerization of glucose ortho esters:: Synthesis of stereoregular 6-deoxy-(1→4)-β-D-glucopyranan [J].
Hori, M ;
Nakatsubo, F .
MACROMOLECULES, 2001, 34 (08) :2476-2481