Regioselective enzymatic synthesis of non-steroidal anti-inflammatory drugs containing glucose in organic media.
Enzymatic transesterification of glucose with the vinyl ester of non-steroidal anti-inflammatory drugs (NSAIDs) was in organic media performed for synthesis of novel NSAIDs-glucose conjugates. Glucose was regioselectively acylated at the 6-hydroxyl group. The indomethacin-glucose conjugate and ketoprofen-glucose conjugate were produced by the catalysis of alkaline protease from Bacillus subtilis in the respective yields of 42% (over 48 h) and 63% (over 40 h). The etodolac-glucose conjugate was obtained in 26% yield (over 144 h) by lipase from Candida antarctica.
Wang
Na
N
Department of Chemistry, Zhejiang University, 310027, Hangzhou, P.R. China.
Liu
Bo Kai
BK
Wu
Qi
Q
Wang
Jun Liang
JL
Lin
Xian Fu
XF
D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry / Q000378:metabolism*; D001412:Bacillus subtilis / Q000201:enzymology; D001426:Bacterial Proteins / Q000378:metabolism*; D002175:Candida / Q000201:enzymology; D002384:Catalysis; D002855:Chromatography, Thin Layer; D010450:Endopeptidases / Q000378:metabolism*; D005947:Glucose / Q000737:chemistry / Q000378:metabolism*; D007213:Indomethacin / Q000737:chemistry / Q000378:metabolism; D007660:Ketoprofen / Q000737:chemistry / Q000378:metabolism; D008049:Lipase / Q000378:metabolism*
D000894:Anti-Inflammatory Agents, Non-Steroidal; D001426:Bacterial Proteins; D007660:Ketoprofen; D008049:Lipase; D010450:Endopeptidases; C087822:alkaline protease; D005947:Glucose; D007213:Indomethacin