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Chemical Compound Review

Dumasin     cyclopentanone

Synonyms: Adipinketon, cyclopentanon, CYCLOPENTANONE, cyclopentyloxy, CHEMBL18620, ...
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Disease relevance of cyclopentanone

  • Cyclopentanone 1,2-monooxygenase, a flavoprotein produced by Pseudomonas sp. strain NCIMB 9872 upon induction by cyclopentanol or cyclopentanone (M. Griffin and P. W. Trudgill, Biochem. J. 129:595-603, 1972), has been utilized as a biocatalyst in Baeyer-Villiger oxidations [1].
  • A heterobicyclic lactone obtained by stereoselective Baeyer-Villiger biooxidation with recombinant whole-cells expressing cyclopentanone monooxygenase from Comamonas sp. NCIMB 9872 was used for formal total syntheses of various natural products containing a tetrahydrofuran structural motif [2].
  • BVMO genes cloned from the first two strains could be expressed to high levels in Escherichia coli using standard expression vectors, and the recombinants converted cyclopentanone and cyclohexanone to the corresponding lactones [3].
  • Although frequently nonenantioselective, cyclopentanone 1,2-monooxygenase was found to exhibit a broader substrate range than the related cyclohexanone 1,2-monooxygenase from Acinetobacter sp. strain NCIMB 9871 [1].
  • This cyclopentanone, the dehydration end product of PGD2, differs from other prostaglandins in several respects [4].

High impact information on cyclopentanone


Chemical compound and disease context of cyclopentanone


Biological context of cyclopentanone


Associations of cyclopentanone with other chemical compounds


Gene context of cyclopentanone

  • We tested the hypothesis that the neuroprotective action of cyclopentanone could be caused partially by an induction of heme oxygenase 1 (HO-1) [15].


  1. Cloning and characterization of a gene cluster involved in cyclopentanol metabolism in Comamonas sp. strain NCIMB 9872 and biotransformations effected by Escherichia coli-expressed cyclopentanone 1,2-monooxygenase. Iwaki, H., Hasegawa, Y., Wang, S., Kayser, M.M., Lau, P.C. Appl. Environ. Microbiol. (2002) [Pubmed]
  2. Accessing tetrahydrofuran-based natural products by microbial Baeyer-Villiger biooxidation. Mihovilovic, M.D., Bianchi, D.A., Rudroff, F. Chem. Commun. (Camb.) (2006) [Pubmed]
  3. Cloning of Baeyer-Villiger monooxygenases from Comamonas, Xanthobacter and Rhodococcus using polymerase chain reaction with highly degenerate primers. Van Beilen, J.B., Mourlane, F., Seeger, M.A., Kovac, J., Li, Z., Smits, T.H., Fritsche, U., Witholt, B. Environ. Microbiol. (2003) [Pubmed]
  4. 15d-PGJ2: the anti-inflammatory prostaglandin? Scher, J.U., Pillinger, M.H. Clin. Immunol. (2005) [Pubmed]
  5. Activation of peroxisome proliferator-activated receptor gamma suppresses nuclear factor kappa B-mediated apoptosis induced by Helicobacter pylori in gastric epithelial cells. Gupta, R.A., Polk, D.B., Krishna, U., Israel, D.A., Yan, F., DuBois, R.N., Peek, R.M. J. Biol. Chem. (2001) [Pubmed]
  6. Asymmetric total synthesis of ent-(-)-roseophilin: assignment of absolute configuration. Boger, D.L., Hong, J. J. Am. Chem. Soc. (2001) [Pubmed]
  7. Structure-based design, synthesis, and memapsin 2 (BACE) inhibitory activity of carbocyclic and heterocyclic peptidomimetics. Hanessian, S., Yun, H., Hou, Y., Yang, G., Bayrakdarian, M., Therrien, E., Moitessier, N., Roggo, S., Veenstra, S., Tintelnot-Blomley, M., Rondeau, J.M., Ostermeier, C., Strauss, A., Ramage, P., Paganetti, P., Neumann, U., Betschart, C. J. Med. Chem. (2005) [Pubmed]
  8. Inhibition of prostaglandin synthesis by sodium 2-[4-(2-oxocyclopentylmethyl)phenyl] propionate dihydrate (CS-600), a new anti-inflammatory drug, and its active metabolite in vitro and in vivo. Matsuda, K., Tanaka, Y., Ushiyama, S., Ohnishi, K., Yamazaki, M. Biochem. Pharmacol. (1984) [Pubmed]
  9. Ligands of the peroxisome proliferator-activated receptors (PPAR-gamma and PPAR-alpha) reduce myocardial infarct size. Wayman, N.S., Hattori, Y., McDonald, M.C., Mota-Filipe, H., Cuzzocrea, S., Pisano, B., Chatterjee, P.K., Thiemermann, C. FASEB J. (2002) [Pubmed]
  10. Design and synthesis of antitumor compounds based on the cytotoxic diterpenoids from the genus Rabdosia. Fuji, K., Xu, H.J., Tatsumi, H., Imahori, H., Ito, N., Node, M., Inaba, M. Chem. Pharm. Bull. (1991) [Pubmed]
  11. Synthesis of [17,18-3H] trans-13-azaprostanoic acid. A labeled probe for the PGH2/TXA2 receptor. Ghali, N.I., Kattelman, E.J., Hung, S.C., Schnorf, K.E., Le Breton, G.C., Venton, D.L. Prostaglandins (1984) [Pubmed]
  12. Biochemical effects and decreased body burden of cyclopentanone by extended vapour inhalation. Elovaara, E., Pfäffli, P., Savolainen, H. Acta pharmacologica et toxicologica. (1984) [Pubmed]
  13. In vitro co-metabolism of ethanol and cyclic ketones. Buszewicz, G., Madro, R. Toxicology (2002) [Pubmed]
  14. Reduction of cycloalkanones by Aspergillus niger. Lemière, G.L., Alderweireldt, F.C. Z. Allg. Mikrobiol. (1975) [Pubmed]
  15. Regulation of heme oxygenase expression by cyclopentenone prostaglandins. Zhuang, H., Pin, S., Li, X., Doré, S. Exp. Biol. Med. (Maywood) (2003) [Pubmed]
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