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Chemical Compound Review

pimelic acid     heptanedioic acid

Synonyms: Pilerate, pimelate, Heptandioate, PubChem20083, Pileric acid, ...
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Disease relevance of pimelic acid


High impact information on pimelic acid

  • Cyclo-3beta-(4-aminophenyl)-2beta-tropanemethanol pimelic acid ester/amide (5b) had an IC50 of 3.8 nM at the DAT [3].
  • The purified enzyme had a pH optimum of approximately 8.0, Km values of 0.49 mM for pimelic acid, 0.18 mM for CoA and 0.72 mM for ATP, a subunit Mr of approximately 80000 as determined by SDS/PAGE, and was found to be a tetramer by gel-filtration chromatography [4].
  • An oligonucleotide gene probe corresponding to one of the amino acid sequences was synthesized and used to isolate the gene (pauA, pimelic acid-utilizing A) coding for pimeloyl-CoA synthetase [4].
  • This acid-CoA ligase exhibited a very sharp substrate specificity, e.g. neither GTP nor pimelate analogues (di- or mono-carboxylic acids) were processed [5].
  • The asymmetric synthesis of both enantiomers of cis-lauthisan (3) is achieved in only six steps from diethyl pimelate (4), the key steps being the diastereodivergent reduction of beta-ketosulfoxide 7 and the highly cis-stereoselective Et(3)SiH/TMSOTf-promoted reductive cyclization of enantiopure hydroxy sulfinyl ketones (S)-14 and (R)-14 [6].

Chemical compound and disease context of pimelic acid

  • Using 8.8 kb of genetic information from Bacillus sphaericus, it was possible to confer to Escherichia coli bio- strains, including delta bioA-D, bioC-, bioH-, the ability to convert exogenous pimelate into biotin [7].

Biological context of pimelic acid

  • The bradytroph phenotype of bioI mutants was overcome by pimelic acid, suggesting that the product of bioI functions at a step prior to pimelic acid synthesis [8].
  • These results suggest that the beta-oxidation enzymes encoded by the pim gene cluster are active with medium-chain-length dicarboxylic acids, including pimelate [9].

Associations of pimelic acid with other chemical compounds


Gene context of pimelic acid

  • In this system, BioI cleaves a carbon-carbon bond of an acyl-ACP to generate a pimeloyl-ACP equivalent, from which pimelic acid is isolated after base-catalyzed saponification [2].

Analytical, diagnostic and therapeutic context of pimelic acid

  • Crystallization of 5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile (1), previously found to produce six conformational polymorphs from solution, on single-crystal pimelic acid (PA) substrates results in selective and oriented growth of the metastable "YN" (yellow needle) polymorph on the (101)(PA) faces of the substrate [14].


  1. To be free or not: the fate of pimelate in Bacillus sphaericus and in Escherichia coli. Lemoine, Y., Wach, A., Jeltsch, J.M. Mol. Microbiol. (1996) [Pubmed]
  2. Expression, purification, and characterization of BioI: a carbon-carbon bond cleaving cytochrome P450 involved in biotin biosynthesis in Bacillus subtilis. Stok, J.E., De Voss, J. Arch. Biochem. Biophys. (2000) [Pubmed]
  3. Synthesis and monoamine transporter binding properties of 2,3-cyclo analogues of 3beta-(4'-aminophenyl)-2beta-tropanemethanol. Carroll, F.I., Blough, B.E., Huang, X., Nie, Z., Mascarella, S.W., Deschamps, J., Navarro, H.A. J. Med. Chem. (2006) [Pubmed]
  4. Purification, characterization, DNA sequence and cloning of a pimeloyl-CoA synthetase from Pseudomonas mendocina 35. Binieda, A., Fuhrmann, M., Lehner, B., Rey-Berthod, C., Frutiger-Hughes, S., Hughes, G., Shaw, N.M. Biochem. J. (1999) [Pubmed]
  5. Investigation of the first step of biotin biosynthesis in Bacillus sphaericus. Purification and characterization of the pimeloyl-CoA synthase, and uptake of pimelate. Ploux, O., Soularue, P., Marquet, A., Gloeckler, R., Lemoine, Y. Biochem. J. (1992) [Pubmed]
  6. Short asymmetric synthesis of (-)- and (+)-cis-lauthisan. Carreño, M.C., Des Mazery, R., Urbano, A., Colobert, F., Solladié, G. Org. Lett. (2005) [Pubmed]
  7. Cloning and characterization of the Bacillus sphaericus genes controlling the bioconversion of pimelate into dethiobiotin. Gloeckler, R., Ohsawa, I., Speck, D., Ledoux, C., Bernard, S., Zinsius, M., Villeval, D., Kisou, T., Kamogawa, K., Lemoine, Y. Gene (1990) [Pubmed]
  8. Cloning, sequencing, and characterization of the Bacillus subtilis biotin biosynthetic operon. Bower, S., Perkins, J.B., Yocum, R.R., Howitt, C.L., Rahaim, P., Pero, J. J. Bacteriol. (1996) [Pubmed]
  9. The pimFABCDE operon from Rhodopseudomonas palustris mediates dicarboxylic acid degradation and participates in anaerobic benzoate degradation. Harrison, F.H., Harwood, C.S. Microbiology (Reading, Engl.) (2005) [Pubmed]
  10. 2-Ketocyclohexanecarboxyl coenzyme A hydrolase, the ring cleavage enzyme required for anaerobic benzoate degradation by Rhodopseudomonas palustris. Pelletier, D.A., Harwood, C.S. J. Bacteriol. (1998) [Pubmed]
  11. Viscosity B-coefficients and activation parameters for viscous flow of a solution of heptanedioic acid in aqueous sucrose solution. Bai, T.C., Yan, G.B. Carbohydr. Res. (2003) [Pubmed]
  12. X-ray studies on crystalline complexes involving amino acids and peptides. XLI. Commonalities in aggregation and conformation revealed by the crystal structures of the pimelic acid complexes of L-arginine and DL-lysine. Saraswathi, N.T., Roy, S., Vijayan, M. Acta Crystallogr., B (2003) [Pubmed]
  13. Formation of a biotin precursor, pimelic acid, in yeasts from C18 fatty acids. Ohsugi, M., Miyauchi, K., Tachibana, K., Nakao, S. J. Nutr. Sci. Vitaminol. (1988) [Pubmed]
  14. Selective nucleation and discovery of organic polymorphs through epitaxy with single crystal substrates. Mitchell, C.A., Yu, L., Ward, M.D. J. Am. Chem. Soc. (2001) [Pubmed]
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