Preparation of biotinylated allosamidins with strong chitinase inhibitory activities.
NaIO4 oxidation of allosamidin (1), a strong inhibitor of family 18 chitinases, followed by a coupling with Biotin Hydrazide afforded its mono- and dibiotinylated derivatives, 4 and 6. Reduction of 4 by NaBH4 afforded its reduced form 5. Each of these three biotinylated derivatives maintained strong chitinase inhibitory activity. Especially, 6 inhibited a Trichoderma chitinase as strongly as 1.
Sakuda
S
S
Department of Applied Biological Chemistry, University of Tokyo, Japan. asakuda@hongo.ecc.u-tokyo.ac.jp
Sakurada
M
M
D000117:Acetylglucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D015374:Biosensing Techniques; D001710:Biotin; D002688:Chitinases / Q000037:antagonists & inhibitors*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D014242:Trichoderma / Q000201:enzymology; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000494:pharmacology
D004791:Enzyme Inhibitors; D014312:Trisaccharides; C054851:allosamidin; D001710:Biotin; D002688:Chitinases; D000117:Acetylglucosamine