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Molecules 2016, 21(11), 1499; doi:10.3390/molecules21111499

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

1
Centre of Innovative and Applied Bioprocessing (CIAB), SAS Nagar, Mohali 160 071, Punjab, India
2
Department of Microbiology, University of Delhi South Campus, Benito Juarez Road, New Delhi 110 021, India
3
Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India
4
Department of Chemistry, Daulat Ram College, University of Delhi, Delhi 110 007, India
5
Department of Chemistry, Kirori Mal College, University of Delhi, Delhi 110 007, India
6
School of Chemical Sciences, Central University of Haryana, Mahendragarh, Haryana 123 029, India
7
Sorbonne Universités, Université de Technologie de Compiègne, EA4297 Transformations Chimiques de la Matière Renouvelable, F-60203 Compiègne CEDEX, France
8
Institute of Advanced Sciences, 410 Faunce Corner Mall Road, Dartmouth, MA 02747, USA
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 31 July 2016 / Revised: 24 October 2016 / Accepted: 2 November 2016 / Published: 9 November 2016
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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. View Full-Text
Keywords: Rhizopus oryzae; lipase; 7,8-Dihydroxy-4-methylcoumarin; regioselectivity; acylation Rhizopus oryzae; lipase; 7,8-Dihydroxy-4-methylcoumarin; regioselectivity; acylation
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MDPI and ACS Style

Kumar, V.; Mathur, D.; Srivastava, S.; Malhotra, S.; Rana, N.; Singh, S.K.; Singh, B.K.; Prasad, A.K.; Varma, A.J.; Len, C.; Kuhad, R.C.; Saxena, R.K.; Parmar, V.S. Biocatalytic Synthesis of Novel Partial Esters of a Bioactive Dihydroxy 4-Methylcoumarin by Rhizopus oryzae Lipase (ROL). Molecules 2016, 21, 1499.

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