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Applied and Environmental Microbiology, November 2009, p. 7135-7141, Vol. 75, No. 22
0099-2240/09/$08.00+0     doi:10.1128/AEM.01277-09
Copyright © 2009, American Society for Microbiology. All Rights Reserved.

Hydroxylation and Further Oxidation of {Delta}9-Tetrahydrocannabinol by Alkane-Degrading Bacteria{triangledown}

Hassan Rashidi,1,2 Muhammad T. Akhtar,1 Frank van der Kooy,1 Robert Verpoorte,1 and Wouter A. Duetz2*

Department of Pharmacognosy, IBL Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands,1 Enzyscreen BV, Biopartner Centre, Wassenaarseweg 72, 2333 AL Leiden, The Netherlands2

Received 3 June 2009/ Accepted 11 September 2009

The microbial biotransformation of {Delta}9-tetrahydrocannabinol was investigated using a collection of 206 alkane-degrading strains. Fifteen percent of these strains, mainly gram-positive strains from the genera Rhodococcus, Mycobacterium, Gordonia, and Dietzia, yielded more-polar derivatives. Eight derivatives were produced on a mg scale, isolated, and purified, and their chemical structures were elucidated with the use of liquid chromatography-mass spectrometry, 1H-nuclear magnetic resonance (1H-NMR), and two-dimensional NMR (1H-1H correlation spectroscopy and heteronuclear multiple bond coherence). All eight biotransformation products possessed modified alkyl chains, with hydroxy, carboxy, and ester functionalities. In a number of strains, β-oxidation of the initially formed C5 carboxylic acid led to the formation of a carboxylic acid lacking two methylene groups.

* Corresponding author. Mailing address: Enzyscreen BV, Biopartner Centre, Wassenaarseweg 72, 2333 AL, Leiden, The Netherlands. Phone: 31 71 3322117. Fax: 31 71 8900519. E-mail: duetz{at}enzyscreen.com

{triangledown} Published ahead of print on 18 September 2009.

Applied and Environmental Microbiology, November 2009, p. 7135-7141, Vol. 75, No. 22
0099-2240/09/$08.00+0     doi:10.1128/AEM.01277-09
Copyright © 2009, American Society for Microbiology. All Rights Reserved.





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