Biocatalytic Synthesis of Novel Partial Esters of a Bioactive Dihydroxy 4-Methylcoumarin by Rhizopus oryzae Lipase (ROL).
Highly regioselective acylation has been observed in 7,8-dihydroxy-4-methylcoumarin (DHMC) by the lipase fromRhizopus oryzaesuspended 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.
Centre of Innovative and Applied Bioprocessing (CIAB), SAS Nagar, Mohali 160 071, Punjab, India. vinod_biodiesel@yahoo.co.in.|Department of Microbiology, University of Delhi South Campus, Benito Juarez Road, New Delhi 110 021, India. vinod_biodiesel@yahoo.co.in.
Vinod
V
Kumar
Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India. dmchem05@gmail.com.|Department of Chemistry, Daulat Ram College, University of Delhi, Delhi 110 007, India. dmchem05@gmail.com.
Divya
D
Mathur
Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India. smritichem10@gmail.com.
Smriti
S
Srivastava
Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India. shashwatmalhotra@gmail.com.|Department of Chemistry, Kirori Mal College, University of Delhi, Delhi 110 007, India. shashwatmalhotra@gmail.com.
Shashwat
S
Malhotra
Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India. neharana256@gmail.com.
Neha
N
Rana
Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India. surajsingh565656@gmail.com.
Suraj K
SK
Singh
Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India. chemquestbk@gmail.com.
Brajendra K
BK
Singh
Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India. ashokenzyme@gmail.com.
Ashok K
AK
Prasad
School of Chemical Sciences, Central University of Haryana, Mahendragarh, Haryana 123 029, India. anjanikumar@cuh.ac.in.
Anjani J
AJ
Varma
Sorbonne Universités, Université de Technologie de Compiègne, EA4297 Transformations Chimiques de la Matière Renouvelable, F-60203 Compiègne CEDEX, France. christophe.len@utc.fr.
Christophe
C
Len
Department of Microbiology, University of Delhi South Campus, Benito Juarez Road, New Delhi 110 021, India. Kuhad85@gmail.com.|School of Chemical Sciences, Central University of Haryana, Mahendragarh, Haryana 123 029, India. Kuhad85@gmail.com.
Ramesh C
RC
Kuhad
Department of Microbiology, University of Delhi South Campus, Benito Juarez Road, New Delhi 110 021, India. rksmicro@yahoo.co.in.
Rajendra K
RK
Saxena
Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India. parmar@cuh.ac.in.|School of Chemical Sciences, Central University of Haryana, Mahendragarh, Haryana 123 029, India. parmar@cuh.ac.in.|Institute of Advanced Sciences, 410 Faunce Corner Mall Road, Dartmouth, MA 02747, USA. parmar@cuh.ac.in.
Virinder S
VS
Parmar
D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D005656:Fungal Proteins / Q000737:chemistry*; D008049:Lipase / Q000737:chemistry*; D015394:Molecular Structure; D012233:Rhizopus / Q000201:enzymology*
D003374:Coumarins; D004952:Esters; D005656:Fungal Proteins; D008049:Lipase
7,8-Dihydroxy-4-methylcoumarin; Rhizopus oryzae; acylation; lipase; regioselectivity