Please use this identifier to cite or link to this item: https://doi.org/10.1002/adsc.200900210
Title: Regio- and stereoselective allylic hydroxylation of D-limonene to (+)-trans-carveol with cellulosimicrobium cellulans EB-8-4
Authors: Wang, Z. 
Lie, F. 
Lim, E.
Li, K.
Li, Z. 
Keywords: Biotransformations
D-limonene
Enzyme catalysis
Hydroxylation
Terpenoids
Trans-carveol
Issue Date: Aug-2009
Source: Wang, Z., Lie, F., Lim, E., Li, K., Li, Z. (2009-08). Regio- and stereoselective allylic hydroxylation of D-limonene to (+)-trans-carveol with cellulosimicrobium cellulans EB-8-4. Advanced Synthesis and Catalysis 351 (11-12) : 1849-1856. ScholarBank@NUS Repository. https://doi.org/10.1002/adsc.200900210
Abstract: Cellulosimicrobium cellulans EB-8-4 was discovered by screening of microorganisms as a pow-erful catalyst for the regio- and stereoselective allylic hydroxylation of D-limonene to (+)-trans-carveol that is a useful and valuable fragrance and flavour compound. Cells of strain EB-8-4 were easily obtained, demonstrated more than 99% regio- and stereoselectivity, showed a specific hydroxylation activity of 4.0 U/g cdw (cell dry weight), and accepted 62 mM D-limonene without inhibition. The hydroxylation was possibly catalyzed by an nicotinamide adenine dinucleotide (NADH)-dependent oxygenase involved in the degradation of aromatic ring during cell growth. 13.4 mM of (+)-trans-carveol were obtained by biohydroxylation of D-limonene with resting cells of C. cellulans EB-8-4, thus being 11 times higher than that obtained with the best biocatalyst known thus far. High conversion and high yield were obtained in the biohydroxylation of 11.6 mM of D-limonene with the resting cells as catalyst in a closed shaking flask, giving 10 mM of (+)-irans-carveol, and 0.30 mM of carvone as the only by-product. Thus, a unique biocatalyst for the regio- and stereoselective allylic hydroxylation of D-limonene and an efficient synthesis of natural identical (.+)-trans-carveol by biohydroxylation have been developed. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
Source Title: Advanced Synthesis and Catalysis
URI: http://scholarbank.nus.edu.sg/handle/10635/64502
ISSN: 16154150
DOI: 10.1002/adsc.200900210
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