N-acetyl-6-sulfo-D-glucosamine as a promising mimic of N-acetyl neuraminic acid

被引：20
作者：
Sasaki, K
Nishida, Y
Uzawa, H
Kobayashi, K [1 ]
机构：
[1] Nagoya Univ, Grad Sch Engn, Dept Mol Design & Engn, Chikusa Ku, Nagoya, Aichi 4648603, Japan
[2] AIST, Tsukuba, Ibaraki 3058565, Japan
[3] JST, CREST, Kawaguchi, Saitama 3320012, Japan
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2003年 / 13卷 / 17期
基金：
日本学术振兴会;
关键词：
D O I：
10.1016/S0960-894X(03)00611-5
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
6-sulfo-D-GlcNAc with a molecular geometry close to that of N-acetylneuraminic acid (Neu5Ac) was hypothesized to serve as a simple Neu5Ac mimic possessing high potential in biochemical and medicinal applications. The hypothesis was evidenced with a neuraminidase inhibition assay using p-nitrophenyl (pNP) 3-, 4-, and 6-sulfo-beta-D-GlcNAc (4, 5 and 2a) and 6-sulfo-beta-D-Glc 6, in which only pNP 6-sulfo-beta-D-GlcNAc 2a was found to show substantial activity. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2821 / 2823
页数：3
相关论文
共 18 条
[1]   Chemical diversity in the sialic acids and related α-keto acids:: An evolutionary perspective [J].
Angata, T ;
Varki, A .
CHEMICAL REVIEWS, 2002, 102 (02) :439-469
[2]   Biosynthesis of L-selectin ligands: Sulfation of sialyl Lewis x-related oligosaccharides by a family of GlcNAc-6-sulfotransferases [J].
Bowman, KG ;
Cook, BN ;
de Graffenried, CL ;
Bertozzi, CR .
BIOCHEMISTRY, 2001, 40 (18) :5382-5391
[3]   Molecular design and biological potential of galacto-type trehalose as a nonnatural ligand of Shiga toxins [J].
Dohi, H ;
Nishida, Y ;
Furuta, Y ;
Uzawa, H ;
Yokoyama, S ;
Ito, S ;
Mori, H ;
Kobayashi, K .
ORGANIC LETTERS, 2002, 4 (03) :355-357
[4]   Recent advances in the synthesis of sialic acid derivatives and sialylmimetics as biological probes [J].
Klefel, MJ ;
von Itzstein, M .
CHEMICAL REVIEWS, 2002, 102 (02) :471-490
[5]   A SINGLE AMINO-ACID RESIDUE CAN DETERMINE THE LIGAND SPECIFICITY OF E-SELECTIN [J].
KOGAN, TP ;
REVELLE, BM ;
TAPP, S ;
SCOTT, D ;
BECK, PJ .
JOURNAL OF BIOLOGICAL CHEMISTRY, 1995, 270 (23) :14047-14055
[6]   Tin-mediated phosphorylation: Synthesis and selectin binding of a phospho Lewis a analog [J].
Manning, DD ;
Bertozzi, CR ;
Rosen, SD ;
Kiessling, LL .
TETRAHEDRON LETTERS, 1996, 37 (12) :1953-1956
[7]  
MISTUOKA C, 1998, J BIOL CHEM, V273, P11225
[8]   A facile synthetic approach to L- and P-selectin blockers via copolymerization of vinyl monomers constructing the key carbohydrate modules of sialyl Lewisx mimics [J].
Nishida, Y ;
Uzawa, H ;
Toba, T ;
Sasaki, K ;
Kondo, H ;
Kobayashi, K .
BIOMACROMOLECULES, 2000, 1 (01) :68-74
[9]   H-1-NMR ANALYSES OF ROTAMERIC DISTRIBUTION OF C5-C6 BONDS OF D-GLUCOPYRANOSES IN SOLUTION [J].
NISHIDA, Y ;
HORI, H ;
OHRUI, H ;
MEGURO, H .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1988, 7 (01) :239-250
[10]   Studies on selectin blocker .1. Structure-activity relationships of sialyl Lewis X analogs [J].
Ohmoto, H ;
Nakamura, K ;
Inoue, T ;
Kondo, N ;
Inoue, Y ;
Yoshino, K ;
Kondo, H ;
Ishida, H ;
Kiso, M ;
Hasegawa, A .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (06) :1339-1343
12