Issue 5, 2013
From the journal:

Green Chemistry

Biocatalysis: fungi mediated novel and selective 12β- or 17β-hydroxylation on the basic limonoid skeleton†‡

Saikat Haldar,a   Swati P. Koleta  and  Hirekodathakallu V. Thulasiram*ab  

* Corresponding authors

a CSIR-National Chemical Laboratory, Department of Organic Chemistry, Pune-411008, India
E-mail: hv.thulasiram@ncl.res.in
Fax: +91 2025902636
Tel: +91 2025902478

b CSIR-Institute of Genomics and Integrative Biology, Mall Road, New Delhi-110007, India

Abstract

Basic limonoids carrying a 4,4,8-trimethyl-17-furanylsteroid skeleton are a class of triterpenoids and well-known for their insecticidal as well as a vast array of pharmacological activities. Rare and synthetically challenging 12β- and 17β-hydroxylation was achieved on the basic limonoid skeleton to produce a novel series of hydroxylated limonoids using fungi-mediated biocatalysis. The fungal system belonging to the genera of Mucor efficiently converted azadiradione, epoxyazadiradione, gedunin and their derivatives into corresponding 12β- and/or 17β-hydroxy derivatives. The position and stereochemistry of hydroxylation was determined by rigorous spectroscopic and crystallographic studies. This fungi-mediated stereo- and regio-selective hydroxylation process was highly efficient and mild enough to sustain chemically sensitive functional groups around the basic limonoid skeleton. Modifications of specific functional groups and variation in biocatalyst were shown to bring selectivity among 12β- or 17β-hydroxylation.

Graphical abstract: Biocatalysis: fungi mediated novel and selective 12β- or 17β-hydroxylation on the basic limonoid skeleton

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Article information

DOI
https://doi.org/10.1039/C3GC40193F
Article type
Paper
Submitted
24 Jan 2013
Accepted
05 Mar 2013
First published
06 Mar 2013

Green Chem., 2013,15, 1311-1317

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Biocatalysis: fungi mediated novel and selective 12β- or 17β-hydroxylation on the basic limonoid skeleton

S. Haldar, S. P. Kolet and H. V. Thulasiram, Green Chem., 2013, 15, 1311 DOI: 10.1039/C3GC40193F

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