Pivalic acid is produced in large quantities by the pharmaceutical industry, and is thought to have minimal toxicity. However, the compound has been found to reduce the fertility of male hamsters (Lewin et al., 1997), and maternal consumption of pivalate in rats has been linked to a predisposition of adult offspring to develop insulin-resistance and obesity (Ricciolini et al., 2001).
Numerous bacterial strains able to degrade pivalic acid have been isolated, including members of families Rhodocyclaceae, Comamonadaceae, and Oxalobacteraceae, , and two pathways were proposed (Probian et al., 2003). After activation with a CoA forming ligase, a pivalyl-CoA mutase is considered to isomerize the quarternary compound. In contrast to the originally proposed pathway, recent studies showed that 3-methylbutyryl-CoA is the product (Katja Zerbe and Jens Harder, personal communication, 2004). In an alternative pathway, strain PIV-34-1, a member of Oxalobacteraceae which is closely related to genus Herbaspirillum, is proposed to degrade pivalate via an anaerobic oxidation of the methyl group, with dimethylmalonate as the initial product (Probian et al., 2003).
The following is a text-format pivalic acid pathway map. Organisms which can initiate the pathway are given, but other organisms may also carry out later steps. Follow the links for more information on compounds or reactions. This map is also available in graphic (5k) format.
Pivalate Pivalate
Strain PIV-34-1 Thauera sp. PIV-1
| Zoogloea resiniphila PIV-3A2w,
| PIV-3A2y, PIV-3C2w, and PIV-3C2y
| |
| |
A v | pivalate-CoA ligase
| |
| |
v v
Dimethylmalonate Pivalyl-CoA
| |
dimethylmalonate | |
decarboxylase | | pivalyl-CoA mutase
| |
| |
v v
Isobutyrate 3-Methylbutyryl-CoA
|
|
|
V
Intermediary
Metabolism
(KEGG)
Page Author(s): Matthew Smith and Carla Essenberg
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