An efficient synthesis of CMP-3-fluoroneuraminic acid

被引:53
作者
Burkart, MD
Vincent, SP
Wong, CH
机构
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
关键词
D O I
10.1039/a903362i
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
CMP-3-fluoroneuraminic acid, a useful mechanistic probe for sialyltransferases, has been efficiently synthesized using recent fluorination and phosphorylation techniques from a sialic acid glycal.
引用
收藏
页码:1525 / 1526
页数:2
相关论文
共 25 条
[1]   DIRECT PREPARATION OF 2-DEOXY-D-GLUCOPYRANOSIDES FROM GLUCALS WITHOUT FERRIER REARRANGEMENT [J].
BOLITT, V ;
MIOSKOWSKI, C ;
LEE, SG ;
FALCK, JR .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (23) :5812-5813
[2]   A new method for the synthesis of fluoro-carbohydrates and glycosides using selectfluor [J].
Burkart, MD ;
Zhang, ZY ;
Hung, SC ;
Wong, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (49) :11743-11746
[3]   Enzyme-catalyzed synthesis of oligosaccharides that contain functionalized sialic acids [J].
Chappell, MD ;
Halcomb, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (14) :3393-3394
[4]  
DABROWSKI U, 1979, TETRAHEDRON LETT, V48, P4637
[5]   INHIBITION OF BACTERIAL AND VIRAL SIALIDASES BY 3-FLUORO-N-ACETYLNEURAMINIC ACID [J].
HAGIWARA, T ;
KIJIMASUDA, I ;
IDO, T ;
OHRUI, H ;
TOMITA, K .
CARBOHYDRATE RESEARCH, 1994, 263 (01) :167-172
[6]   1994, the year of sialyltransferases [J].
HarduinLepers, A ;
Recchi, MA ;
Delannoy, P .
GLYCOBIOLOGY, 1995, 5 (08) :741-758
[7]   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
[8]   Acid-catalyzed solvolysis of CMP-N-acetyl neuraminate: Evidence for a sialyl cation with a finite lifetime [J].
Horenstein, BA ;
Bruner, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (43) :10371-10379
[9]   SYNTHESIS OF METHYL 6'-DEOXY-LACTOSAMINIDES AND 6'-THIO-LACTOSAMINIDES AND THEIR INHIBITORY ACTIVITY TOWARD CMP-NEUNAC-D-GALACTOSIDE-(2-]6)-ALPHA-D-SIALYLTRANSFERASE [J].
KAJIHARA, Y ;
HASHIMOTO, H ;
KODAMA, H ;
WAKABAYASHI, T ;
SATO, K .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1993, 12 (07) :991-995
[10]   CHARACTERIZATION OF INHIBITORY ACTIVITIES AND BINDING MODE OF SYNTHETIC 6'-MODIFIED METHYL N-ACETYL-BETA-LACTOSAMINIDE TOWARD RAT-LIVER CMP-DEUTERIUM-NEU5ACDEUTERIUM-GALACTOSIDE-(2-]6)-ALPHA-DEUTERIUM-SIALYLTRANSFERASE [J].
KAJIHARA, Y ;
KODAMA, H ;
WAKABAYASHI, T ;
SATO, K ;
HASHIMOTO, H .
CARBOHYDRATE RESEARCH, 1993, 247 :179-193