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Biocatalytic Synthesis of Novel Partial Esters of a Bioactive Dihydroxy 4-Methylcoumarin by Rhizopus oryzae Lipase (ROL).


ABSTRACT: Highly regioselective acylation has been observed in 7,8-dihydroxy-4-methylcoumarin (DHMC) by the lipase from Rhizopus oryzae suspended in tetrahydrofuran (THF) at 45 °C using six different acid anhydrides as acylating agents. The acylation occurred regioselectively at one of the two hydroxy groups of the coumarin moiety resulting in the formation of 8-acyloxy-7-hydroxy-4-methylcoumarins, which are important bioactive molecules for studying biotansformations in animals, and are otherwise very difficult to obtain by only chemical steps. Six monoacylated, monohydroxy 4-methylcoumarins have been biocatalytically synthesised and identified on the basis of their spectral data and X-ray crystal analysis.

SUBMITTER: Kumar V 

PROVIDER: S-EPMC6273029 | biostudies-literature | 2016 Nov

REPOSITORIES: biostudies-literature

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Biocatalytic Synthesis of Novel Partial Esters of a Bioactive Dihydroxy 4-Methylcoumarin by Rhizopus oryzae Lipase (ROL).

Kumar Vinod V   Mathur Divya D   Srivastava Smriti S   Malhotra Shashwat S   Rana Neha N   Singh Suraj K SK   Singh Brajendra K BK   Prasad Ashok K AK   Varma Anjani J AJ   Len Christophe C   Kuhad Ramesh C RC   Saxena Rajendra K RK   Parmar Virinder S VS  

Molecules (Basel, Switzerland) 20161109 11


Highly regioselective acylation has been observed in 7,8-dihydroxy-4-methylcoumarin (DHMC) by the lipase from <i>Rhizopus oryzae</i> suspended in tetrahydrofuran (THF) at 45 °C using six different acid anhydrides as acylating agents. The acylation occurred regioselectively at one of the two hydroxy groups of the coumarin moiety resulting in the formation of 8-acyloxy-7-hydroxy-4-methylcoumarins, which are important bioactive molecules for studying biotansformations in animals, and are otherwise  ...[more]

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