Regioselective Esterification of Cardiac Glycosides Catalyzed by Novozym 435 and Lipase PS in Organic Solvents
The enzymatic acetylation in the organic solvents of a number of the important bioactive cardiac glycosides was investigated. With the bufanolide proscillaridin A and the cardenolide lanatoside C, acylation, as expected, occurred at the secondary 4′-OH of the rhamnopyranosyl unit of the former (by t...
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| Format: | Article |
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MDPI AG
2023-04-01
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| Series: | Catalysts |
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| Online Access: | https://www.mdpi.com/2073-4344/13/5/819 |
| _version_ | 1797600742269255680 |
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| author | Ivan Bassanini Lucia Roncaglia Bruno Danieli Sergio Riva |
| author_facet | Ivan Bassanini Lucia Roncaglia Bruno Danieli Sergio Riva |
| author_sort | Ivan Bassanini |
| collection | DOAJ |
| description | The enzymatic acetylation in the organic solvents of a number of the important bioactive cardiac glycosides was investigated. With the bufanolide proscillaridin A and the cardenolide lanatoside C, acylation, as expected, occurred at the secondary 4′-OH of the rhamnopyranosyl unit of the former (by the action of Novozym 435 lipase) and the primary 6′′′′-OH of the terminal glucopyranosyl unit of the latter (best results obtained by the action of the lipase PS). Only lipase PS was found to be able to acylate the cardenolides digitoxin and digoxin at the 4‴-OH of their terminal digitoxose unit. The corresponding monoacetyl derivatives, both of which are commercialized drugs, could be isolated with good yields. The investigation of the Novozym 435-catalyzed acetylation of free <i>D</i>-digitoxose provided a possible explanation for the inability of this lipase to acylate digitoxin and digoxin. |
| first_indexed | 2024-03-11T03:52:12Z |
| format | Article |
| id | doaj.art-e06ef263b1914b96b18d649a1a182ee6 |
| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-11T03:52:12Z |
| publishDate | 2023-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Catalysts |
| spelling | doaj.art-e06ef263b1914b96b18d649a1a182ee62023-11-18T00:50:38ZengMDPI AGCatalysts2073-43442023-04-0113581910.3390/catal13050819Regioselective Esterification of Cardiac Glycosides Catalyzed by Novozym 435 and Lipase PS in Organic SolventsIvan Bassanini0Lucia Roncaglia1Bruno Danieli2Sergio Riva3Istituto di Scienze e Tecnologie Chimiche “Giulio Natta”—SCITEC, Consiglio Nazionale delle Ricerche, via Mario Bianco 9, 20131 Milano, ItalyIstituto di Scienze e Tecnologie Chimiche “Giulio Natta”—SCITEC, Consiglio Nazionale delle Ricerche, via Mario Bianco 9, 20131 Milano, ItalyDipartimento di Chimica, Università degli Studi di Milano, via Camillo Golgi 19, 20131 Milano, ItalyIstituto di Scienze e Tecnologie Chimiche “Giulio Natta”—SCITEC, Consiglio Nazionale delle Ricerche, via Mario Bianco 9, 20131 Milano, ItalyThe enzymatic acetylation in the organic solvents of a number of the important bioactive cardiac glycosides was investigated. With the bufanolide proscillaridin A and the cardenolide lanatoside C, acylation, as expected, occurred at the secondary 4′-OH of the rhamnopyranosyl unit of the former (by the action of Novozym 435 lipase) and the primary 6′′′′-OH of the terminal glucopyranosyl unit of the latter (best results obtained by the action of the lipase PS). Only lipase PS was found to be able to acylate the cardenolides digitoxin and digoxin at the 4‴-OH of their terminal digitoxose unit. The corresponding monoacetyl derivatives, both of which are commercialized drugs, could be isolated with good yields. The investigation of the Novozym 435-catalyzed acetylation of free <i>D</i>-digitoxose provided a possible explanation for the inability of this lipase to acylate digitoxin and digoxin.https://www.mdpi.com/2073-4344/13/5/819cardiac glycosidesNovozym 435Lipase psbiocatalysisregioselective esterificationorganic solvents |
| spellingShingle | Ivan Bassanini Lucia Roncaglia Bruno Danieli Sergio Riva Regioselective Esterification of Cardiac Glycosides Catalyzed by Novozym 435 and Lipase PS in Organic Solvents Catalysts cardiac glycosides Novozym 435 Lipase ps biocatalysis regioselective esterification organic solvents |
| title | Regioselective Esterification of Cardiac Glycosides Catalyzed by Novozym 435 and Lipase PS in Organic Solvents |
| title_full | Regioselective Esterification of Cardiac Glycosides Catalyzed by Novozym 435 and Lipase PS in Organic Solvents |
| title_fullStr | Regioselective Esterification of Cardiac Glycosides Catalyzed by Novozym 435 and Lipase PS in Organic Solvents |
| title_full_unstemmed | Regioselective Esterification of Cardiac Glycosides Catalyzed by Novozym 435 and Lipase PS in Organic Solvents |
| title_short | Regioselective Esterification of Cardiac Glycosides Catalyzed by Novozym 435 and Lipase PS in Organic Solvents |
| title_sort | regioselective esterification of cardiac glycosides catalyzed by novozym 435 and lipase ps in organic solvents |
| topic | cardiac glycosides Novozym 435 Lipase ps biocatalysis regioselective esterification organic solvents |
| url | https://www.mdpi.com/2073-4344/13/5/819 |
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