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

Kenji Sasaki; Yoshihiro Nishida; Hirotaka Uzawa; Kazukiyo Kobayashi

doi:10.1016/s0960-894x(03)00611-5

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

Bioorg Med Chem Lett. 2003 Sep 1;13(17):2821-3. doi: 10.1016/s0960-894x(03)00611-5.

Authors

Kenji Sasaki¹, Yoshihiro Nishida, Hirotaka Uzawa, Kazukiyo Kobayashi

Affiliation

¹ Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Nagoya, Japan.

PMID: 14611836
DOI: 10.1016/s0960-894x(03)00611-5

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetylglucosamine / analogs & derivatives*
Acetylglucosamine / pharmacology
Biomimetic Materials / chemistry
Biomimetic Materials / pharmacology
Enzyme Inhibitors / chemistry
Enzyme Inhibitors / pharmacology
Models, Molecular
Molecular Conformation
N-Acetylneuraminic Acid / analogs & derivatives*
Neuraminidase / antagonists & inhibitors
Vibrio cholerae / enzymology

Substances

Enzyme Inhibitors
Neuraminidase
N-Acetylneuraminic Acid
Acetylglucosamine