Total synthesis and structural revision of TMG-chitotriomycin, a specific inhibitor of insect and fungal beta-N-acetylglucosaminidases.
TMG-chitotriomycin, a potent and selective inhibitor of the beta-N-acetylglucosaminidases that possesses an unique N,N,N-trimethyl-d-glucosamine (TMG) residue, is revised to be the TMG-beta-(1-->4)-chitotriose instead of the originally proposed alpha-anomer via its total synthesis, for which a highly convergent approach was developed in which the sterically demanding (1-->4)-glycosidic linkages are efficiently constructed by the Au(I)-catalyzed glycosylation protocol with glycosyl o-hexynylbenzoates as donors.
Yang
You
Y
State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.
Li
Yao
Y
Yu
Biao
B
D000118:Acetylglucosaminidase / Q000037:antagonists & inhibitors*; D000818:Animals; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D005658:Fungi / Q000201:enzymology*; D006801:Humans; D007313:Insecta / Q000201:enzymology*; D013379:Substrate Specificity; D013402:Sugar Alcohols / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology
D004791:Enzyme Inhibitors; D013402:Sugar Alcohols; C528826:TMG-chitotriomycin; D000118:Acetylglucosaminidase