Regioselective Enzymatic Synthesis of Kojic Acid Monoesters
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 selec...
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MDPI AG
2021-11-01
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| Series: | Catalysts |
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| Online Access: | https://www.mdpi.com/2073-4344/11/12/1430 |
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| author | Klaudia Karkeszová Mária Mastihubová Vladimír Mastihuba |
| author_facet | Klaudia Karkeszová Mária Mastihubová Vladimír Mastihuba |
| author_sort | Klaudia Karkeszová |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-10T04:31:16Z |
| format | Article |
| id | doaj.art-db3fa1b19b6b4bcbab83a33960c72c77 |
| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-10T04:31:16Z |
| publishDate | 2021-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Catalysts |
| spelling | doaj.art-db3fa1b19b6b4bcbab83a33960c72c772023-11-23T04:08:49ZengMDPI AGCatalysts2073-43442021-11-011112143010.3390/catal11121430Regioselective Enzymatic Synthesis of Kojic Acid MonoestersKlaudia Karkeszová0Mária Mastihubová1Vladimír Mastihuba2Department of Chemical and Biochemical Engineering, Institute of Chemical and Environmental Engineering, Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, 811 07 Bratislava, SlovakiaLaboratory of Biocatalysis and Organic Synthesis, Institute of Chemistry, Slovak Academy of Sciences, Dúbravská Cesta 9, 845 38 Bratislava, SlovakiaLaboratory of Biocatalysis and Organic Synthesis, Institute of Chemistry, Slovak Academy of Sciences, Dúbravská Cesta 9, 845 38 Bratislava, SlovakiaKojic 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.https://www.mdpi.com/2073-4344/11/12/1430kojic acidpig pancreatic lipaseacylationalcoholysisregioselectivity |
| spellingShingle | Klaudia Karkeszová Mária Mastihubová Vladimír Mastihuba Regioselective Enzymatic Synthesis of Kojic Acid Monoesters Catalysts kojic acid pig pancreatic lipase acylation alcoholysis regioselectivity |
| title | Regioselective Enzymatic Synthesis of Kojic Acid Monoesters |
| title_full | Regioselective Enzymatic Synthesis of Kojic Acid Monoesters |
| title_fullStr | Regioselective Enzymatic Synthesis of Kojic Acid Monoesters |
| title_full_unstemmed | Regioselective Enzymatic Synthesis of Kojic Acid Monoesters |
| title_short | Regioselective Enzymatic Synthesis of Kojic Acid Monoesters |
| title_sort | regioselective enzymatic synthesis of kojic acid monoesters |
| topic | kojic acid pig pancreatic lipase acylation alcoholysis regioselectivity |
| url | https://www.mdpi.com/2073-4344/11/12/1430 |
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