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8703259 
Journal Article 
Formation of (+)-cis-2,3-Dihydroxy-1-methylcyclohexa-4,6-diene from Toluene by Pseudomonas putida 
Gibson, DT; Hensley, M; Yoshioka, H; Mabry, TJ 
1970 
Yes 
Biochemistry
ISSN: 0006-2960
EISSN: 1520-4995 
9 
7 
1626-1630 
English 
Toluene is oxidized by a mutant strain of Pseudomonas putida (strain 39/D) to (+)-cis-2,3-dihydroxy-1-methylcyclohexa-4,6-diene. Acetylation of this product followed by condensation with maleic anhydride results in the formation of 1-methyl-2,3-diacetoxybicyclo(2,2,2)-7-hexene-5,6-dicarboxylic anhydride. The nuclear magnetic resonance spectrum of the condensation product establishes the cis configuration of the hydroxyl groups in the toluene oxidation product. Washed cells of P. putida (parent strain) and cell extracts prepared from the same organism rapidly oxidize toluene, 3-methylcatechol, and (+)-cis-2,3-dihydroxy-l-methylcyclohexa-4,6-diene. The latter compound is enzymatically dehydrogenated by cell extracts, prepared from the parent organism, to form 3-methylcatechol. This reaction occurs under anaerobic conditions and oxidized nicotinamide-adenine dinucleotide is an essential cofactor for the reaction. The data presented provide evidence that (+)-cis-2,3-dihydroxy-1-methylcyclohexa-4,6-diene is an intermediate in the degradation of toluene by P. putida. 1970, American Chemical Society. All rights reserved.