Synthesis of Long Chain Fatty Acids Acylated Coumarin Glycoside Esters with Lipase as Catalyst

doi:10.1007/s40242-015-5048-8

Chemical Research in Chinese Universities ›› 2015, Vol. 31 ›› Issue (4): 534-538.doi: 10.1007/s40242-015-5048-8

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Synthesis of Long Chain Fatty Acids Acylated Coumarin Glycoside Esters with Lipase as Catalyst

LIU Duo, CAI Shuanglian, LUAN Fangjian, WANG Qiu'an

State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China

Received:2015-02-04 Revised:2015-03-16 Online:2015-08-01 Published:2015-04-13
Contact: WANG Qiu'an E-mail:WangQA@hnu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(Nos.21342015, J1210040) and the Hunan Provincial Natural Science Foundation, China(No.14JJ2048).

Abstract

Abstract:

A series of novel coumarin glycoside esters(1―9) was synthesized through the acylation reaction of 4-methylcoumarin-7-O-β-D-glucoside(11) with different long chain fatty acids catalyzed by lipase in organic medium. The acylation occurred regioselectively at the 6'-OH of glycosyl moiety. The enzymatic synthesis was optimized to achieve 54%―70% yield using immobilized lipase(Novozym 435, 10 mg/mL) as catalyst and acetone and pyridine(9:1, volume ratio, water content<1%) as solvent with an acyl donor/coumarin glycoside molar ratio of 10:1 at a temperature of 40―50 ℃ for 96 h. All the synthesized compounds were confirmed.

Key words: Coumarin glycoside, Lipase-catalyzed acylation, Long chain fatty acid, Regioselective acylation

LIU Duo, CAI Shuanglian, LUAN Fangjian, WANG Qiu'an. Synthesis of Long Chain Fatty Acids Acylated Coumarin Glycoside Esters with Lipase as Catalyst[J]. Chemical Research in Chinese Universities, 2015, 31(4): 534-538.

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Synthesis of Long Chain Fatty Acids Acylated Coumarin Glycoside Esters with Lipase as Catalyst

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