Efficiently enhancing regioselective acylation of 5‐azacytidine catalysed by Candida antarctica lipase B with co‐solvent mixtures as the reaction media
A comparative study of regioselective acylation of 5‐azacytidine catalysed by CAL‐B ( Candida antarctica lipase B) in co‐solvent mixtures and in pure organic solvents was performed, to our knowledge for the first time, and it was shown that a remarkable enhancement in the initial rate and substrate...
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crwiley:10.1042/ba20080178 2024-06-02T07:56:30+00:00 Efficiently enhancing regioselective acylation of 5‐azacytidine catalysed by Candida antarctica lipase B with co‐solvent mixtures as the reaction media Wu, Hong Zong, Minhua Chen, Xiyu 2009 http://dx.doi.org/10.1042/ba20080178 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1042%2FBA20080178 https://iubmb.onlinelibrary.wiley.com/doi/pdf/10.1042/BA20080178 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Biotechnology and Applied Biochemistry volume 53, issue 3, page 201-207 ISSN 0885-4513 1470-8744 journal-article 2009 crwiley https://doi.org/10.1042/ba20080178 2024-05-03T12:06:33Z A comparative study of regioselective acylation of 5‐azacytidine catalysed by CAL‐B ( Candida antarctica lipase B) in co‐solvent mixtures and in pure organic solvents was performed, to our knowledge for the first time, and it was shown that a remarkable enhancement in the initial rate and substrate conversion in the reaction could be achieved with co‐solvents as the reaction medium instead of pure organic solvents. For the CAL‐B‐catalysed regioselective synthesis of 5′‐ O ‐butyryl‐5‐azacytidine in co‐solvent mixtures, the optimal conditions were as follows: optimal co‐solvent mixture, hexane/pyridine (40/60, v/v); initial a w (water activity), 0.07; enzyme dosage, 50 units/ml; vinyl butyrate/5‐azacytidine molar ratio, 15:1; temperature, 60 °C. Under the optimal conditions, v 0 (the initial reaction rate), C (the substrate conversion) and the regioselectivity of the reaction were 0.75 mM/min, 99.0% and above 99% respectively. Similar phenomena were observed in the CAL‐B‐catalysed regioselective acylation of 5‐azacytidine with an extensive range of fatty acid vinyl esters (from C2 to C18). Compared with pure pyridine, the reactions were greatly accelerated in a hexane/pyridine (40/60, v/v) co‐solvent mixture and 5‐azacytidine could be biotransformed into its derivative 5′‐ O ‐acyl‐5‐azacytidine at a much higher conversion rate (91.4–99.0% as against 40.2–43.5%). Meanwhile, adoption of a co‐solvent mixture as the reaction medium could also greatly lower the enzyme dosage and the molar ratio of acyl donor to 5‐azacytidine. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library Biotechnology and Applied Biochemistry |
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A comparative study of regioselective acylation of 5‐azacytidine catalysed by CAL‐B ( Candida antarctica lipase B) in co‐solvent mixtures and in pure organic solvents was performed, to our knowledge for the first time, and it was shown that a remarkable enhancement in the initial rate and substrate conversion in the reaction could be achieved with co‐solvents as the reaction medium instead of pure organic solvents. For the CAL‐B‐catalysed regioselective synthesis of 5′‐ O ‐butyryl‐5‐azacytidine in co‐solvent mixtures, the optimal conditions were as follows: optimal co‐solvent mixture, hexane/pyridine (40/60, v/v); initial a w (water activity), 0.07; enzyme dosage, 50 units/ml; vinyl butyrate/5‐azacytidine molar ratio, 15:1; temperature, 60 °C. Under the optimal conditions, v 0 (the initial reaction rate), C (the substrate conversion) and the regioselectivity of the reaction were 0.75 mM/min, 99.0% and above 99% respectively. Similar phenomena were observed in the CAL‐B‐catalysed regioselective acylation of 5‐azacytidine with an extensive range of fatty acid vinyl esters (from C2 to C18). Compared with pure pyridine, the reactions were greatly accelerated in a hexane/pyridine (40/60, v/v) co‐solvent mixture and 5‐azacytidine could be biotransformed into its derivative 5′‐ O ‐acyl‐5‐azacytidine at a much higher conversion rate (91.4–99.0% as against 40.2–43.5%). Meanwhile, adoption of a co‐solvent mixture as the reaction medium could also greatly lower the enzyme dosage and the molar ratio of acyl donor to 5‐azacytidine. |
format |
Article in Journal/Newspaper |
author |
Wu, Hong Zong, Minhua Chen, Xiyu |
spellingShingle |
Wu, Hong Zong, Minhua Chen, Xiyu Efficiently enhancing regioselective acylation of 5‐azacytidine catalysed by Candida antarctica lipase B with co‐solvent mixtures as the reaction media |
author_facet |
Wu, Hong Zong, Minhua Chen, Xiyu |
author_sort |
Wu, Hong |
title |
Efficiently enhancing regioselective acylation of 5‐azacytidine catalysed by Candida antarctica lipase B with co‐solvent mixtures as the reaction media |
title_short |
Efficiently enhancing regioselective acylation of 5‐azacytidine catalysed by Candida antarctica lipase B with co‐solvent mixtures as the reaction media |
title_full |
Efficiently enhancing regioselective acylation of 5‐azacytidine catalysed by Candida antarctica lipase B with co‐solvent mixtures as the reaction media |
title_fullStr |
Efficiently enhancing regioselective acylation of 5‐azacytidine catalysed by Candida antarctica lipase B with co‐solvent mixtures as the reaction media |
title_full_unstemmed |
Efficiently enhancing regioselective acylation of 5‐azacytidine catalysed by Candida antarctica lipase B with co‐solvent mixtures as the reaction media |
title_sort |
efficiently enhancing regioselective acylation of 5‐azacytidine catalysed by candida antarctica lipase b with co‐solvent mixtures as the reaction media |
publisher |
Wiley |
publishDate |
2009 |
url |
http://dx.doi.org/10.1042/ba20080178 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1042%2FBA20080178 https://iubmb.onlinelibrary.wiley.com/doi/pdf/10.1042/BA20080178 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Biotechnology and Applied Biochemistry volume 53, issue 3, page 201-207 ISSN 0885-4513 1470-8744 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1042/ba20080178 |
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Biotechnology and Applied Biochemistry |
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