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13C-1 phenol was converted to 13C-4 benzoic acid by an anaerobic phenol converting enrichment, which did not form p-hydroxybenzoate as a free intermediate but converted p-hydroxybenzoate first phenol and then, probably by another organism, to benzoate. No isotopic effect was observed using D5- and D6-phenol, suggesting that the breakage of the C-H bond on the C-4 position was not a rate limiting step in the conversion.
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Zhang et al. (1990) studied this question.
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