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

Molecules

卷:21

Brajendra K. Singh¹  Smriti Srivastava¹  Shashwat Malhotra¹  Divya Mathur¹  Virinder S. Parmar¹  Neha Rana¹  Ashok K. Prasad¹  Suraj K. Singh¹  Vinod Kumar²  Rajendra K. Saxena³  Ramesh C. Kuhad³  Anjani J. Varma⁴  Christophe Len⁵ 

[1] Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India;

[2] Centre of Innovative and Applied Bioprocessing (CIAB), SAS Nagar, Mohali 160 071, Punjab, India;

[3] Department of Microbiology, University of Delhi South Campus, Benito Juarez Road, New Delhi 110 021, India;

[4] School of Chemical Sciences, Central University of Haryana, Mahendragarh, Haryana 123 029, India;

[5] Sorbonne Universités, Université de Technologie de Compiègne, EA4297 Transformations Chimiques de la Matière Renouvelable, F-60203 Compiègne CEDEX, France;

关键词: Rhizopus oryzae;    lipase;    7,8-Dihydroxy-4-methylcoumarin;    regioselectivity;    acylation;   

DOI  :  10.3390/molecules21111499

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown