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

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

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N,N,N-Trimethyl-D-glucosamine(TMG)-chitotriomycin,a naturally occurring chitin related oligosaccharide,is a specific β-N-acetylhexo-saminidases(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 disac-charide 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.

CarbohydratesGlycosylationChitosanOligosaccharidesBiocatalysis

Jianghua Li、Yan Zhang、Zhifei Hu、Jinfeng Ye、Hongzhi Cao

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Key Laboratory of Marine Drugs of Ministry of Education,Shandong Key Laboratory of Glycoscience and Glycotechnology,School of Medicine and Pharmacy,Ocean University of China,Qingdao,Shandong 266003,China

Laboratory for Marine Drugs and Bioproducts,Laoshan Laboratory,Qingdao,Shandong 266237,China

2024

10.1002/cjoc.202400345

中国化学(英文版)
中国化学会 上海有机化学研究所

中国化学(英文版)

CSTPCD
影响因子：0.848
ISSN：1001-604X
年,卷(期)：2024.42(19)