Chemoenzymatic Synthesis of N,N,N-Trimethyl-D-Glucosamine Chitotriomycin and Its Analogues
Jianghua Li , Yan Zhang , Zhifei Hu , Jinfeng Ye , Hongzhi Cao
Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (19) : 2293 -2298.
Chemoenzymatic Synthesis of N,N,N-Trimethyl-D-Glucosamine Chitotriomycin and Its Analogues
N, N, N-Trimethyl-D-glucosamine (TMG)-chitotriomycin, a naturally occurring chitin related oligosaccharide, is a specific β- 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.
Carbohydrates / Glycosylation / Chitosan / Oligosaccharides / Biocatalysis
2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
/
| 〈 |
|
〉 |
PDF
