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Microbiology and Molecular Biology Reviews, September 2008, p. 445-456, Vol. 72, No. 3
1092-2172/08/$08.00+0     doi:10.1128/MMBR.00005-08
Copyright © 2008, American Society for Microbiology. All Rights Reserved.

Getting a Handle on the Role of Coenzyme M in Alkene Metabolism

Arathi M. Krishnakumar,1 Darius Sliwa,1 James A. Endrizzi,1 Eric S. Boyd,1 Scott A. Ensign,2 and John W. Peters1*

Department of Chemistry and Biochemistry, Montana State University, Bozeman, Montana 59717,1 Department of Chemistry and Biochemistry, Utah State University, Logan, Utah 843222

Summary: Coenzyme M (2-mercaptoethanesulfonate; CoM) is one of several atypical cofactors discovered in methanogenic archaea which participate in the biological reduction of CO2 to methane. Elegantly simple, CoM, so named for its role as a methyl carrier in all methanogenic archaea, is the smallest known organic cofactor. It was thought that this cofactor was used exclusively in methanogenesis until it was recently discovered that CoM is a key cofactor in the pathway of propylene metabolism in the gram-negative soil microorganism Xanthobacter autotrophicus Py2. A four-step pathway requiring CoM converts propylene and CO2 to acetoacetate, which feeds into central metabolism. In this process, CoM is used to activate and convert highly electrophilic epoxypropane, formed from propylene epoxidation, into a nucleophilic species that undergoes carboxylation. The unique properties of CoM provide a chemical handle for orienting compounds for site-specific redox chemistry and stereospecific catalysis. The three-dimensional structures of several of the enzymes in the pathway of propylene metabolism in defined states have been determined, providing significant insights into both the enzyme mechanisms and the role of CoM in this pathway. These studies provide the structural basis for understanding the efficacy of CoM as a handle to direct organic substrate transformations at the active sites of enzymes.

* Corresponding author. Mailing address: Chemistry and Biochemistry Building, Montana State University, Bozeman, MT 59717. Phone: (406) 994-7211. Fax: (406) 994-7470. E-mail: john.peters{at}chemistry.montana.edu

Microbiology and Molecular Biology Reviews, September 2008, p. 445-456, Vol. 72, No. 3
1092-2172/08/$08.00+0     doi:10.1128/MMBR.00005-08
Copyright © 2008, American Society for Microbiology. All Rights Reserved.





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