期刊
CATALYSTS
卷 11, 期 12, 页码 -出版社
MDPI
DOI: 10.3390/catal11121430
关键词
kojic acid; pig pancreatic lipase; acylation; alcoholysis; regioselectivity
资金
- Slovak Research and Development Agency [CA18224]
- Slovak Grant Agency for Science VEGA [2/0126/19]
- [APVV-18-0188]
The study demonstrates that kojic acid esters can be produced by various enzymes with different regioselectivity, with pig pancreatic lipase showing distinct stereo selectivity in the reaction.
Kojic acid is a fungal metabolite and one of the strongest tyrosinase inhibitors. Its esters are used as lipid-compatible skin whitening components in cosmetic formulations. In this study, lipase PS, lipase AK, Lipolyve AN and pig pancreatic lipase catalyzed the acetylation of kojic acid under selective formation of the same product, kojic 7-acetate. However, the enzymes differed in their regioselectivity when catalyzing the alcoholysis of kojic acid diacetate. While lipase PS and lipase AK produced mixtures of both monoacetate regioisomers (7-acetate and 5-acetate of kojic acid), the pancreatic lipase almost exclusively produced 5-acetate. The enzyme displayed the same regioselectivity in the palmitoylation of kojic acid and in the alcoholysis of kojic acid dipalmitate. Simple reaction engineering with PPL as a catalyst thus provides the complementary monoesters of kojic acid. Kojic 7-acetate, 5-acetate, 7-palmitate and 5-palmitate were prepared with yields after purification of 57.3%, 38.2%, 31.7% and 31.4%, respectively.
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