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Applied and Environmental Microbiology, February 2007, p. 930-938, Vol. 73, No. 3
0099-2240/07/$08.00+0     doi:10.1128/AEM.02227-06
Copyright © 2007, American Society for Microbiology. All Rights Reserved.

Cyclohexane Carboxylate and Benzoate Formation from Crotonate in Syntrophus aciditrophicus{triangledown}

Housna Mouttaki,1 Mark A. Nanny,2 and Michael J. McInerney1*

Department of Botany and Microbiology,1 Department of Civil and Environmental Engineering, University of Oklahoma, Norman, Oklahoma2

Received 21 September 2006/ Accepted 29 November 2006

The anaerobic, syntrophic bacterium Syntrophus aciditrophicus grown in pure culture produced 1.4 ± 0.24 mol of acetate and 0.16 ± 0.02 mol of cyclohexane carboxylate per mole of crotonate metabolized. [U-13C]crotonate was metabolized to [1,2-13C]acetate and [1,2,3,4,5,7-13C]cyclohexane carboxylate. Cultures grown with unlabeled crotonate and [13C]sodium bicarbonate formed [6-13C]cyclohexane carboxylate. Trimethylsilyl (TMS) derivatives of cyclohexane carboxylate, cyclohex-1-ene carboxylate, benzoate, pimelate, glutarate, 3-hydroxybutyrate, and acetoacetate were detected as intermediates by comparison of retention times and mass spectral profiles to authentic standards. With [U-13C]crotonate, the m/z-15 ion of TMS-derivatized glutarate, 3-hydroxybutyrate, and acetoacetate each increased by +4 mass units, and the m/z-15 ion of TMS-derivatized pimelate, cyclohex-1-ene carboxylate, benzoate, and cyclohexane carboxylate each increased by +6 mass units. With [13C]sodium bicarbonate and unlabeled crotonate, the m/z-15 ion of TMS derivatives of glutarate, pimelate, cyclohex-1-ene carboxylate, benzoate, and cyclohexane carboxylate each increased by +1 mass unit, suggesting that carboxylation occurred after the synthesis of a four-carbon intermediate. With [1,2-13C]acetate and unlabeled crotonate, the m/z-15 ion of TMS-derivatized 3-hydroxybutyrate, acetoacetate, and glutarate each increased by +0, +2, and +4 mass units, respectively, and the m/z-15 ion of TMS-derivatized pimelate, cyclohex-1-ene carboxylate, benzoate, cyclohexane carboxylate, and 2-hydroxycyclohexane carboxylate each increased by +0, +2, +4, and +6 mass units. The data are consistent with a pathway for cyclohexane carboxylate formation involving the condensation of two-carbon units derived from crotonate degradation with CO2 addition, rather than the use of the intact four-carbon skeleton of crotonate.

* Corresponding author. Mailing address: Department of Botany and Microbiology, University of Oklahoma, 770 Van Vleet Oval, Norman, OK 73019. Phone: (405) 325-6050. Fax: (405) 325-7619. E-mail: mcinerney{at}ou.edu.

{triangledown} Published ahead of print on 8 December 2006.

Applied and Environmental Microbiology, February 2007, p. 930-938, Vol. 73, No. 3
0099-2240/07/$08.00+0     doi:10.1128/AEM.02227-06
Copyright © 2007, American Society for Microbiology. All Rights Reserved.



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