N-Acetyl-6-sulfo-D-glucosamine as a promising mimic of N-Acetyl neuraminic acid.
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.
Sasaki
Kenji
K
Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Nagoya, Japan.
Nishida
Yoshihiro
Y
Uzawa
Hirotaka
H
Kobayashi
Kazukiyo
K
D000117:Acetylglucosamine / Q000031:analogs & derivatives* / Q000494:pharmacology; D040761:Biomimetic Materials / Q000737:chemistry / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000494:pharmacology; D008958:Models, Molecular; D008968:Molecular Conformation; D019158:N-Acetylneuraminic Acid / Q000031:analogs & derivatives*; D009439:Neuraminidase / Q000037:antagonists & inhibitors; D014734:Vibrio cholerae / Q000201:enzymology
D004791:Enzyme Inhibitors; D009439:Neuraminidase; D019158:N-Acetylneuraminic Acid; D000117:Acetylglucosamine