Chemoenzymatic Synthesis of N,N,N-Trimethyl-D-Glucosamine Chitotriomycin and Its Analogues  

作　　者：Jianghua Li Yan Zhang Zhifei Hu Jinfeng Ye Hongzhi Cao 

机构地区：[1]Key Laboratory of Marine Drugs of Ministry of Education,Shandong Key Laboratory of Glycoscience and Glycotechnology,School of Medicine and Pharmacy,Ocean Universityof China,Qingdao,Shandong 266003,China [2]b Laboratory for Marine Drugs and Bioproducts,Laoshan Laboratory,Qingdao,Shandong 266237,China

出　　处：《Chinese Journal of Chemistry》2024年第19期2293-2298,共6页中国化学（英文版）

基　　金：supported by the National Key Research and Development Program of China(2021YFC2101500);the National Natural Science Foundation of China(22277111 and 22107094);Taishan Scholar Project(TSTP20221114);Department of Science and Technology of Shandong Province(2020CXGC010601,ZR2023ZD45,and ZR2021QB061).

摘　　要：Comprehensive Summary,N,N,N-Trimethyl-D-glucosamine(TMG)-chitotriomycin,a naturally occurring chitin related oligosaccharide,is a specificβ-N-acetylhexosaminidases(HexNAcases)inhibitor for insects and fungi.Although TMG-chitoriomycin holds great promise as a novel class insecticide and fungicide,the limited accessibility of TMG-chitotriomycin prevents its further biological evaluation.We report herein a simple and eco-friendly chemoenzymatic approach for the efficient synthesis of TMG-chitotriomycin and its analogues.In this strategy,the readily available chitosan was enzymatically hydrolyzed and chemically N-acetylated to afford the chitooligosaccharides ranging from disaccharide to hexasaccharide.These chitooligosaccharides were selectively deacetylated by two different chitin deacetylases followed by chemical N-trimethylation to obtain the desired TMG-chitotriomycin and a total of 13 TMG-chitotriomycin analogues in the longest linear sequence of 4 steps in over 12%total yields.

关 键 词：Carbohydrates GLYCOSYLATION Chitosan OLIGOSACCHARIDES BIOCATALYSIS 

分 类 号：O62[理学—有机化学]