Enzymatic n-acylation and n-transacylation of d-glucosamine

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Mini symposium: Glycobiology at the LUMC and beyond

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Enzymatic n-acylation and n-transacylation of d-glucosamine

Pedro Laborda 1 , Yong-Mei Lyu 1 , Li Liu 1 , Josef Voglmeir 1

1 Glycomics and Glycan Bioengineering Research Center, College of Food Science and Technology, Nanjing Agricultural University, Nanjing, China

We previously reported the isolation and characterization of a bacterial deacetylase (CmCBDA), which catalyzes selectively the hydrolysis of GlcNAc to glucosamine under mild reaction conditions[1]. This CmCBDA deacetylase was further studied and demonstrated to catalyze the N-acylation of unprotected glucosamine and to N-transacylate unprotected N-acetylglucosamine at ambient temperatures. A wide range of N-acylglucosamine derivatives bearing aliphatic chains or different functional groups suitable for further incorporation reactions were obtained in high conversion rates. Furthermore, CmCBDA catalyzed the N-acylation of glucosamine and was used in an enzymatic cascade for the synthesis of sialosides.

CmCBDA-catalyzed acylation of glucosamine 1 to provide N-acylglucosamines 2-8.

Lv Y.M.; Laborda P.; Huang K.; Cai Z.P.; Wang M.; Lu A.M.; Doherthy C.; Liu L.; Flitsch S.L.; Voglmeir J. Green Chemistry 2017, 19, 527-535.

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