Enzymatic synthesis of fluorinated mechanistic probes for sialidases and sialyltransferases

被引:59
作者
Chokhawala, Harshal A. [1 ]
Cao, Hongzhi [1 ]
Yu, Hai [1 ]
Chen, Xi [1 ]
机构
[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA
关键词
D O I
10.1021/ja072687u
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A general, convenient, and efficient enzymatic approach for producing fluorinated mechanistic probes for sialidases and sialyltransferases is described. Other than the reported sialyltransferase inhibitor CMP-3F(axial)Neu5Ac, CIVIP-3F (equatorial)Sia derivatives (in which Sia is Neu5Ac or Neu5Gc) have been synthesized along with CMP-3F (axial)Neu5Gc and CMP-3F(axia/)KDN as novel inhibitors and important mechanistic probes for sialyltransferases. 3-Fluoro-sialosides have been enzymatically synthesized and could be used as potential inhibitors and mechanistic probes for sialidases and as probes for sialic acid-binding proteins.
引用
收藏
页码:10630 / +
页数:3
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共 26 条
[1]   Synthetic potential of cloned fucosyl-transferase III and VI [J].
Baisch, G ;
Ohrlein, R ;
Katopodis, A ;
Streiff, M ;
Kolbinger, F .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (19) :2447-2450
[2]  
BELICZEY J, 2002, Patent No. 6355253
[3]   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
[4]   An efficient synthesis of CMP-3-fluoroneuraminic acid [J].
Burkart, MD ;
Vincent, SP ;
Wong, CH .
CHEMICAL COMMUNICATIONS, 1999, (16) :1525-1526
[5]   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
[6]   Preparation of fluorinated galactosyl nucleoside diphosphates to study the mechanism of the enzyme galactopyranose mutase [J].
Burton, A ;
Wyatt, P ;
Boons, GJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (16) :2375-2382
[7]   Structural analysis of the sialyltransferase CstII from Campylobacter jejuni in complex with a substrate analog [J].
Chiu, CPC ;
Watts, AG ;
Lairson, LL ;
Gilbert, M ;
Lim, D ;
Wakarchuk, WW ;
Withers, SG ;
Strynadka, NCJ .
NATURE STRUCTURAL & MOLECULAR BIOLOGY, 2004, 11 (02) :163-170
[8]   BACTERIAL SIALIDASES - ROLES IN PATHOGENICITY AND NUTRITION [J].
CORFIELD, T .
GLYCOBIOLOGY, 1992, 2 (06) :509-521
[9]   An O-glycoside of sialic acid derivative that inhibits both hemagglutinin and sialidase activities of influenza viruses [J].
Guo, CT ;
Sun, XL ;
Kanie, O ;
Shortridge, KF ;
Suzuki, T ;
Miyamoto, D ;
Hidari, KIPJ ;
Wong, CH ;
Suzuki, Y .
GLYCOBIOLOGY, 2002, 12 (03) :183-190
[10]   1994, the year of sialyltransferases [J].
HarduinLepers, A ;
Recchi, MA ;
Delannoy, P .
GLYCOBIOLOGY, 1995, 5 (08) :741-758