Biocatalytic Synthesis of Novel Partial Esters of a Bioactive Dihydroxy 4-Methylcoumarin by Rhizopus oryzae Lipase (ROL)
Vinod Kumar,
Divya Mathur,
Smriti Srivastava,
Shashwat Malhotra,
Neha Rana,
Suraj K. Singh,
Brajendra K. Singh,
Ashok K. Prasad,
Anjani J. Varma,
Christophe Len,
Ramesh C. Kuhad,
Rajendra K. Saxena,
Virinder S. Parmar
Affiliations
Vinod Kumar
Centre of Innovative and Applied Bioprocessing (CIAB), SAS Nagar, Mohali 160 071, Punjab, India
Divya Mathur
Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India
Smriti Srivastava
Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India
Shashwat Malhotra
Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India
Neha Rana
Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India
Suraj K. Singh
Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India
Brajendra K. Singh
Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India
Ashok K. Prasad
Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India
Anjani J. Varma
School of Chemical Sciences, Central University of Haryana, Mahendragarh, Haryana 123 029, India
Christophe Len
Sorbonne Universités, Université de Technologie de Compiègne, EA4297 Transformations Chimiques de la Matière Renouvelable, F-60203 Compiègne CEDEX, France
Ramesh C. Kuhad
Department of Microbiology, University of Delhi South Campus, Benito Juarez Road, New Delhi 110 021, India
Rajendra K. Saxena
Department of Microbiology, University of Delhi South Campus, Benito Juarez Road, New Delhi 110 021, India
Virinder S. Parmar
Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India
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.
