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Appl Environ Microbiol. 1994 November; 60(11): 4111-4115

Regiospecificity of Chlorophenol Reductive Dechlorination by Vitamin B_12s

Mark H. Smith and Sandra L. Woods^*

¹ Environmental and Water Resources Engineering Program, Department of Civil Engineering, Oregon State University, Corvallis, Oregon 97331-2302

ABSTRACT

Vitamin B₁₂, reduced by titanium (III) citrate to vitamin B_12s, catalyzes the reductive dechlorination of chlorophenols. Reductive dechlorination of pentachlorophenol and of all tetrachlorophenol and trichlorophenol isomers was observed. Reaction of various chlorophenols with vitamin B₁₂ favored reductive dechlorination at positions adjacent to another chlorinated carbon, but chlorines ortho to the hydroxyl group of a phenol were particularly resistant to reductive dechlorination, even if they were also ortho to a chlorine. This resulted in a reductive dechlorination pattern favoring removal of para and meta chlorines, which differs substantially from the pattern exhibited by anaerobic microbial consortia.

^* Corresponding author. Mailing address: Environmental and Water Resources Engineering Program, Department of Civil Engineering, Apperson 202, Oregon State University, Corvallis, OR 97331-2302. Phone: (503) 737-6837. Fax: (503) 737-3099.

Present address: Armstrong Laboratory, AL/EQW, Tyndall AFB, FL 32403-5323.