Abstract
Occurrence, biosynthesis, and biodegradation of pivalic acid and other compounds, having a quaternary carbon atom by different bacteria, are described. We have summarized the relevant data that have so far been published, presenting them in a graphical form, i.e., as biodegradation pathways including B12-dependent isomerization and desaturation that lead to the degradation of pivalic acid and similar compounds to products with other than quaternary carbon atoms, i.e., compounds whose catabolism is well known.
Similar content being viewed by others
References
Bisel P, Al-Momani L, Müller M (2008) The tert-butyl group in chemistry and biology. Org Biomol Chem 6:2655–2665
Brass EP (2002) Pivalate-generating prodrugs and carnitine homeostasis in man. Pharm Rev 54:589–598
Cracan V, Banerjee R (2012) Novel coenzyme B12-dependent interconversion of isovaleryl-CoA and pivalyl-CoA. J Biol Chem 287:3723–3732
Czerkawski JW (1976) The use of pivalic acid as a reference substance in measurements of production of volatile fatty acids by rumen microorganisms in vitro. Br J Nutr 36:311–315
Dembitsky VM (2006) Natural neo acids and neo alkanes: their analogs and derivatives. Lipids 41:309–340
Ettwig KF, Butler MK, Le Paslier D, Pelletier E, Mangenot S, Kuypers MMM, Schreiber F, Dutilh BE, Zedelius J, De Beer D, Gloerich J, Wessels HJCT, Van Alen T, Luesken F, Wu ML, Van De Pas-Schoonen KT, Op Den Camp HJM, Janssen-Megens EM, Francoijs KJ, Stunnenberg H, Weissenbach J, Jetten MSM, Strous M (2010) Nitrite-driven anaerobic methane oxidation by oxygenic bacteria. Nature 464:543–548
Giner JL (1993) Biosynthesis of marine sterol side chains. Chem Rev 93:1735–1752
Gouda H, Kobayashi Y, Yamada T, Ideguchi T, Sugawara A, Hirose T, Omura S, Sunazuka T, Hirono S (2012) Three-dimensional solution structure of bottromycin A2: a potent antibiotic active against methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococci. Chem Pharm Bull 60:169–171
Irie K, Kajiyama IS, Funaki A, Koshimizu K, Hayashi H, Araia M (1990) Biosynthesis of indole alkaloid tumor promoters teleocidins (I) possible biosynthetic pathway of the monoterpenoid moieties of teleocidins. Tetrahedron 46:2773–2788
Kaneda T (1991) Iso- and anteiso-fatty acids in bacteria: biosynthesis, function, and taxonomic significance. Microbiol Rev 55:288–302
Kenig F, Simons DJ, Crich D, Cowen JP, Ventura GT, Rehbein-Khalily T, Brown TC, Anderson KB (2003) Branched aliphatic alkanes with quaternary substituted carbon atoms in modern and ancient geologic samples. Proc Natl Acad Sci U S A 100:12554–12558
Kniemeyer O, Probian C, Rossello-Mora R, Harder J (1999) Anaerobic mineralization of quaternary carbons atoms: isolation of denitrifying bacteria on dimethylmalonate. Appl Environ Microbiol 65:3319–3324
Moore BS, Eisenberg R, Weber C, Bridges A, Nanz D, Robinson JA (1995) On the stereospecificity of the coenzyme B12-dependent isobutyryl-CoA mutase reaction. J Am Chem Soc 117:11285–11291
Müller RH, Rohwerder T, Harms H (2008) Degradation of fuel oxygenates and their main intermediates by Aquincola tertiaricarbonis L108. Microbiology 154:1414–1421
Probian C, Wulfing A, Harder J (2003) Anaerobic mineralization of quaternary carbon atoms: isolation of denitrifying bacteria on pivalic acid (2,2-dimethylpropionic acid). Appl Environ Microbiol 69:1866–1870
Ratnatilleke A, Vrijbloed JW, Robinson JA (1999) Cloning and sequencing of the coenzyme B12-binding domain of isobutyryl-CoA mutase from Streptomyces cinnamonensis, reconstitution of mutase activity, and characterization of the recombinant enzyme produced in Escherichia coli. J Biol Chem 274:31679–31685
Reaxys (2012) Reaxys. https://www.reaxys.com. Accessed 5 May 2012
Rétey J, Smith EH, Zagalak B (1978) Investigation of the mechanism of the methylmalonyl-CoA mutase reaction with substrate analogue: ethylmalonyl-CoA. Eur J Biochem 83:437–451
Rezanka T, Siristova L, Schreiberova O, Rezanka M, Masak J, Melzoch K, Sigler K (2011) Pivalic acid acts as a starter unit in a fatty acid and antibiotic biosynthetic pathway in Alicyclobacillus, Rhodococcus and Streptomyces. Environ Microbiol 13:1577–1589
Schäfer F, Muzica L, Schuster J, Treuter N, Rosell M, Harms H, Müller RH, Rohwerder T (2011) Formation of alkenes via degradation of tert-alkyl ethers and alcohols by Aquincola tertiaricarbonis L108 and Methylibium spp. Appl Environ Microbiol 77:5981–5987
Shinichi T, Padmakumar R, Lai M, Liu H, Banerjee R (1994) Inhibition of the human methylmalonyl-CoA mutase by various CoA-esters. J Biol Chem 269:31630–31634
Sin SN, Chua H (2000) Degradation pathway of persistent branched fatty acids in natural anaerobic ecosystem. Chemosphere 41:149–153
Solano-Serena F, Marchal R, Casarégola S, Vasnier C, Lebeault JM, Vandecasteele JP (2000) A Mycobacterium strain with extended capacities for degradation of gasoline hydrocarbons. Appl Environ Microbiol 66:2392–2399
Solano-Serena F, Marchal R, Heiss S, Vandecasteele JP (2004) Degradation of isooctane by Mycobacterium austroafricanum IFP 2173: growth and catabolic pathway. J Appl Microbiol 97:629–639
Strømgaard K, Nakanishi K (2004) Chemistry and biology of terpene trilactones from Ginkgo biloba. Angew Chem Int Ed 43:1640–1658
Willecke K, Pardee AB (1971) Fatty acid-requiring mutant of Bacillus subtilis defective in branched chain alpha-keto acid dehydrogenase. J Biol Chem 246:5264–5272
Acknowledgments
The research was supported by the projects GACR P503/11/0215 and MSM6046137305 and by the Institutional Internal Project RVO61388971.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Řezanka, T., Kolouchová, I., Čejková, A. et al. Biosynthesis and metabolic pathways of pivalic acid. Appl Microbiol Biotechnol 95, 1371–1376 (2012). https://doi.org/10.1007/s00253-012-4267-x
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00253-012-4267-x