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

页码：2821 / 2823

页数：3

共 18 条

[1] Chemical diversity in the sialic acids and related α-keto acids:: An evolutionary perspective
Angata, T
Varki, A
[J]. 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
Bowman, KG
Cook, BN
de Graffenried, CL
Bertozzi, CR
[J]. BIOCHEMISTRY, 2001, 40 (18) : 5382 - 5391
[3] Molecular design and biological potential of galacto-type trehalose as a nonnatural ligand of Shiga toxins
Dohi, H
Nishida, Y
Furuta, Y
Uzawa, H
Yokoyama, S
Ito, S
Mori, H
Kobayashi, K
[J]. ORGANIC LETTERS, 2002, 4 (03) : 355 - 357
[4] Recent advances in the synthesis of sialic acid derivatives and sialylmimetics as biological probes
Klefel, MJ
von Itzstein, M
[J]. CHEMICAL REVIEWS, 2002, 102 (02) : 471 - 490
[5] A SINGLE AMINO-ACID RESIDUE CAN DETERMINE THE LIGAND SPECIFICITY OF E-SELECTIN
KOGAN, TP
REVELLE, BM
TAPP, S
SCOTT, D
BECK, PJ
[J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 1995, 270 (23) : 14047 - 14055
[6] Tin-mediated phosphorylation: Synthesis and selectin binding of a phospho Lewis a analog
Manning, DD
Bertozzi, CR
Rosen, SD
Kiessling, LL
[J]. 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
Nishida, Y
Uzawa, H
Toba, T
Sasaki, K
Kondo, H
Kobayashi, K
[J]. BIOMACROMOLECULES, 2000, 1 (01) : 68 - 74
[9] H-1-NMR ANALYSES OF ROTAMERIC DISTRIBUTION OF C5-C6 BONDS OF D-GLUCOPYRANOSES IN SOLUTION
NISHIDA, Y
HORI, H
OHRUI, H
MEGURO, H
[J]. JOURNAL OF CARBOHYDRATE CHEMISTRY, 1988, 7 (01) : 239 - 250
[10] Studies on selectin blocker .1. Structure-activity relationships of sialyl Lewis X analogs
Ohmoto, H
Nakamura, K
Inoue, T
Kondo, N
Inoue, Y
Yoshino, K
Kondo, H
Ishida, H
Kiso, M
Hasegawa, A
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (06) : 1339 - 1343

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