Enzymatic synthesis of fluorinated mechanistic probes for sialidases and sialyltransferases

被引：58

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 35期

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

页码：10630 / +

页数：3

共 26 条

[1] Synthetic potential of cloned fucosyl-transferase III and VI
Baisch, G
Ohrlein, R
Katopodis, A
Streiff, M
Kolbinger, F
[J]. 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
Burkart, MD
Zhang, ZY
Hung, SC
Wong, CH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (49) : 11743 - 11746
[4] An efficient synthesis of CMP-3-fluoroneuraminic acid
Burkart, MD
Vincent, SP
Wong, CH
[J]. CHEMICAL COMMUNICATIONS, 1999, (16) : 1525 - 1526
[5] Chemo-enzymatic synthesis of fluorinated sugar nucleotide:: Useful mechanistic probes for glycosyltransferases
Burkart, MD
Vincent, SP
Düffels, A
Murray, BW
Ley, SV
Wong, CH
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (08) : 1937 - 1946
[6] Preparation of fluorinated galactosyl nucleoside diphosphates to study the mechanism of the enzyme galactopyranose mutase
Burton, A
Wyatt, P
Boons, GJ
[J]. 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
Chiu, CPC
Watts, AG
Lairson, LL
Gilbert, M
Lim, D
Wakarchuk, WW
Withers, SG
Strynadka, NCJ
[J]. NATURE STRUCTURAL & MOLECULAR BIOLOGY, 2004, 11 (02) : 163 - 170
[8] BACTERIAL SIALIDASES - ROLES IN PATHOGENICITY AND NUTRITION
CORFIELD, T
[J]. GLYCOBIOLOGY, 1992, 2 (06) : 509 - 521
[9] An O-glycoside of sialic acid derivative that inhibits both hemagglutinin and sialidase activities of influenza viruses
Guo, CT
Sun, XL
Kanie, O
Shortridge, KF
Suzuki, T
Miyamoto, D
Hidari, KIPJ
Wong, CH
Suzuki, Y
[J]. GLYCOBIOLOGY, 2002, 12 (03) : 183 - 190
[10] 1994, the year of sialyltransferases
HarduinLepers, A
Recchi, MA
Delannoy, P
[J]. GLYCOBIOLOGY, 1995, 5 (08) : 741 - 758

← 1 2 3 →