The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.

wikigene or wiki gene protein drug chemical gene disease author authorship tracking collaborative publishing evolutionary knowledge reputation system wiki2.0 global collaboration genes proteins drugs chemicals diseases compound
Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

Cyclopropan     cyclopropane

Synonyms: Zyklopropan, CYCLOPROPANE, Trimethylene, ciclopropano, cyclopropanum, ...
Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of cyclopropane

  • A novel mycolic acid cyclopropane synthetase is required for cording, persistence, and virulence of Mycobacterium tuberculosis [1].
  • We identified a mycobacterial gene, pcaA, that we show is required for cording and mycolic acid cyclopropane ring synthesis in the cell wall of both BCG and M. tuberculosis [1].
  • This activity was localized to a single gene (cma1) encoding a protein that was 34% identical to the cyclopropane fatty acid synthase from Escherichia coli [2].
  • Calcipotriol (MC903) is a side chain analog of the vitamin D hormone calcitriol, containing a 22-23 double bond, a 24(S)-hydroxyl function, and carbons 25, 26, and 27 incorporated into a cyclopropane ring which has been developed for treating psoriasis [3].
  • Cyclopropane-derived peptidomimetics. Design, synthesis, evaluation, and structure of novel HIV-1 protease inhibitors [4].

High impact information on cyclopropane


Chemical compound and disease context of cyclopropane


Biological context of cyclopropane

  • The gene whose product cyclopropanates the proximal double bond was cloned by homology to a putative cyclopropane synthase identified from the Mycobacterium leprae genome sequencing project [14].
  • Independent confirmation of the SEs of a series of substituted cyclopropenes is provided by their dimerization/combination with cyclopropane to form a six-membered ring reference compound [15].
  • However, it is also likely that Ser-78 serves as the active site nucleophile that attacks the cyclopropane ring and initiates the fragmentation of ACC, while the conserved Lys-51 is the base required for beta-H abstraction [16].
  • A structure-activity relationship study of spirolactones. Contribution of the cyclopropane ring to antimineralocorticoid activity [17].
  • Catalytic hydrogenation of 1 leads to consecutive opening of the two cyclopropane rings to give C(2)-bisseco-octahedrane (pentacyclo[,6).0(3,11).0(4,9)]dodecane) 16 as the major product [18].

Anatomical context of cyclopropane

  • Purified TDM isolated from a cyclopropane-deficient pcaA mutant was hypoinflammatory for macrophages and induced less severe granulomatous inflammation in mice, demonstrating that the fine structure of this glycolipid was critical to its proinflammatory activity [19].
  • Accordingly, as demonstrated in gel filtration experiments, flavohemoglobin is able to bind liposomes obtained from lipid extracts of E. coli membranes and eventually abstract phospholipids containing cis double bonds and/or cyclopropane rings along the acyl chains [20].
  • The effects of the enantiomers of (+/-)-CAMP and (+/-)-TAMP [(+/-)-cis- and (+/-)-trans-2-aminomethylcyclopropanecarboxylic acids, respectively], which are cyclopropane analogues of GABA, were tested on GABA(A) and GABA(C) receptors expressed in Xenopus laevis oocytes using two-electrode voltage clamp methods [21].
  • We compared peripheral nerve regeneration in adult rats with sciatic nerve gaps of 16 mm after autologous transplantation of GFP-labeled SDSCs into two different types of guides: a synthetic guide, obtained by dip coating with a L-lactide and trimethylene carbonate (PLA-TMC) copolymer and a collagen-based guide [22].
  • In biological assays conducted in an AP1 cell line expressing the human NHE-1 isoform, the starting cyclopropane 3a (IC(50) = 3.5 microM) shows inhibitory activity comparable to cariporide (IC(50) = 3.4 microM) [23].

Associations of cyclopropane with other chemical compounds

  • Analysis by proton NMR indicates that the mycolic acids of the cmaA2 mutant lack trans-cyclopropane rings but are otherwise intact with respect to cyclopropane and methyl branch content [24].
  • The CH2I-I species readily reacts with ethylene to give the cyclopropane product and an I2 product via a one-step reaction with a barrier height of approximately 2.9 kcal/mol [25].
  • Oxidation-reduction chemistry of DL-alpha-lipoic acid, propanedithiol, and trimethylene disulfide in aprotic and in aqueous media [26].
  • The trimethylene- and biphenylene-bridged cations D(CH(2))(3)D*(+) and D(ph)(2)D*(+) with highly localized charge distributions are prototypical class II systems involving moderately coupled redox centers with H approximately equal to 400 cm(-1) [27].
  • These derivatives are characterized by having a fluorine atom at the 2-position on the cyclopropane ring as the N1 substituent and consist of both cis and trans stereoisomers [28].

Gene context of cyclopropane

  • It is demonstrated that introduction of appropriate hydrophobic groups at the phenyl ring and a gem-dimethyl group at the cyclopropane ring enhances the NHE-1 inhibitory activity by up to 3 orders of magnitude (compound 7f, IC(50) = 0.003 microM) [23].
  • The 3' end of the ribC gene is directly adjacent to the cfa gene, which codes for cyclopropane-fatty-acid synthase [29].
  • Our previous studies have shown that 1,1-dichloro-cis-2,3-diaryl cyclopropane (Analog II), a diarylcyclopropyl compound is devoid of estrogenic activity, has a weak binding affinity for the estrogen receptor in the mouse uterine tissue and inhibits the growth of breast cancer cells in culture [30].
  • Unlike the parent 1-phenylcyclopropylamine, which is a selective inhibitor of MAO B, both (E)- and (Z)-diastereomers of derivatives having fluorine at the 2-position of the cyclopropane ring were potent and selective irreversible inhibitors of MAO A [31].
  • A striking effect was observed for derivatives 3d and 3f, whose 5-HT1A affinity was reinforced by two orders of magnitude with a simultaneous decrease in 5-HT2A binding constants in comparison with trimethylene analogues [32].

Analytical, diagnostic and therapeutic context of cyclopropane


  1. A novel mycolic acid cyclopropane synthetase is required for cording, persistence, and virulence of Mycobacterium tuberculosis. Glickman, M.S., Cox, J.S., Jacobs, W.R. Mol. Cell (2000) [Pubmed]
  2. Identification of a gene involved in the biosynthesis of cyclopropanated mycolic acids in Mycobacterium tuberculosis. Yuan, Y., Lee, R.E., Besra, G.S., Belisle, J.T., Barry, C.E. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  3. In vitro metabolism of the anti-psoriatic vitamin D analog, calcipotriol, in two cultured human keratinocyte models. Masuda, S., Strugnell, S., Calverley, M.J., Makin, H.L., Kremer, R., Jones, G. J. Biol. Chem. (1994) [Pubmed]
  4. Cyclopropane-derived peptidomimetics. Design, synthesis, evaluation, and structure of novel HIV-1 protease inhibitors. Martin, S.F., Dorsey, G.O., Gane, T., Hillier, M.C., Kessler, H., Baur, M., Mathä, B., Erickson, J.W., Bhat, T.N., Munshi, S., Gulnik, S.V., Topol, I.A. J. Med. Chem. (1998) [Pubmed]
  5. Carbocyclic fatty acids in plants: biochemical and molecular genetic characterization of cyclopropane fatty acid synthesis of Sterculiafoetida. Bao, X., Katz, S., Pollard, M., Ohlrogge, J. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  6. The mmaA2 gene of Mycobacterium tuberculosis encodes the distal cyclopropane synthase of the alpha-mycolic acid. Glickman, M.S. J. Biol. Chem. (2003) [Pubmed]
  7. Reaction intermediate structures of 1-aminocyclopropane-1-carboxylate deaminase: insight into PLP-dependent cyclopropane ring-opening reaction. Ose, T., Fujino, A., Yao, M., Watanabe, N., Honma, M., Tanaka, I. J. Biol. Chem. (2003) [Pubmed]
  8. Characterization of cyclopropane fatty-acid synthase from Sterculia foetida. Bao, X., Thelen, J.J., Bonaventure, G., Ohlrogge, J.B. J. Biol. Chem. (2003) [Pubmed]
  9. Cyclopropane-containing polyamine analogues are efficient growth inhibitors of a human prostate tumor xenograft in nude mice. Frydman, B., Blokhin, A.V., Brummel, S., Wilding, G., Maxuitenko, Y., Sarkar, A., Bhattacharya, S., Church, D., Reddy, V.K., Kink, J.A., Marton, L.J., Valasinas, A., Basu, H.S. J. Med. Chem. (2003) [Pubmed]
  10. Fluorine-19 nuclear magnetic resonance studies of lipid fatty acyl chain order and dynamics in Acholeplasma laidlawii B membranes. A direct comparison of the effects of cis and trans cyclopropane ring and double-bond substituents on orientational order. Macdonald, P.M., Sykes, B.D., McElhaney, R.N. Biochemistry (1985) [Pubmed]
  11. Differentiation of Campylobacter and Campylobacter-like organisms by cellular fatty acid composition. Lambert, M.A., Patton, C.M., Barrett, T.J., Moss, C.W. J. Clin. Microbiol. (1987) [Pubmed]
  12. Methyl sterol and cyclopropane fatty acid composition of Methylococcus capsulatus grown at low oxygen tensions. Jahnke, L.L., Nichols, P.D. J. Bacteriol. (1986) [Pubmed]
  13. Properties and biosynthesis of cyclopropane fatty acids in Escherichia coli. Cronan, J.E., Reed, R., Taylor, F.R., Jackson, M.B. J. Bacteriol. (1979) [Pubmed]
  14. The biosynthesis of cyclopropanated mycolic acids in Mycobacterium tuberculosis. Identification and functional analysis of CMAS-2. George, K.M., Yuan, Y., Sherman, D.R., Barry, C.E. J. Biol. Chem. (1995) [Pubmed]
  15. Strain energy of small ring hydrocarbons. Influence of C-h bond dissociation energies. Bach, R.D., Dmitrenko, O. J. Am. Chem. Soc. (2004) [Pubmed]
  16. Reaction of 1-amino-2-methylenecyclopropane-1-carboxylate with 1-aminocyclopropane-1-carboxylate deaminase: analysis and mechanistic implications. Zhao, Z., Chen, H., Li, K., Du, W., He, S., Liu, H.W. Biochemistry (2003) [Pubmed]
  17. A structure-activity relationship study of spirolactones. Contribution of the cyclopropane ring to antimineralocorticoid activity. Chinn, L.J., Salamon, K.W., Desai, B.N. J. Med. Chem. (1981) [Pubmed]
  18. Preparation and reactivity of [D3d]-octahedrane: the most stable (CH)12 hydrocarbon. de Meijere, A., Lee, C.H., Kuznetsov, M.A., Gusev, D.V., Kozhushkov, S.I., Fokin, A.A., Schreiner, P.R. Chemistry (Weinheim an der Bergstrasse, Germany) (2005) [Pubmed]
  19. Mycobacterium tuberculosis controls host innate immune activation through cyclopropane modification of a glycolipid effector molecule. Rao, V., Fujiwara, N., Porcelli, S.A., Glickman, M.S. J. Exp. Med. (2005) [Pubmed]
  20. Interaction with membrane lipids and heme ligand binding properties of Escherichia coli flavohemoglobin. Bonamore, A., Farina, A., Gattoni, M., Schininà, M.E., Bellelli, A., Boffi, A. Biochemistry (2003) [Pubmed]
  21. (+)- and (-)-cis-2-aminomethylcyclopropanecarboxylic acids show opposite pharmacology at recombinant rho(1) and rho(2) GABA(C) receptors. Duke, R.K., Chebib, M., Balcar, V.J., Allan, R.D., Mewett, K.N., Johnston, G.A. J. Neurochem. (2000) [Pubmed]
  22. Skin-derived stem cells transplanted into resorbable guides provide functional nerve regeneration after sciatic nerve resection. Marchesi, C., Pluderi, M., Colleoni, F., Belicchi, M., Meregalli, M., Farini, A., Parolini, D., Draghi, L., Fruguglietti, M.E., Gavina, M., Porretti, L., Cattaneo, A., Battistelli, M., Prelle, A., Moggio, M., Borsa, S., Bello, L., Spagnoli, D., Gaini, S.M., Tanzi, M.C., Bresolin, N., Grimoldi, N., Torrente, Y. Glia (2007) [Pubmed]
  23. Arylcyclopropanecarboxyl guanidines as novel, potent, and selective inhibitors of the sodium hydrogen exchanger isoform-1. Ahmad, S., Doweyko, L.M., Dugar, S., Grazier, N., Ngu, K., Wu, S.C., Yost, K.J., Chen, B.C., Gougoutas, J.Z., DiMarco, J.D., Lan, S.J., Gavin, B.J., Chen, A.Y., Dorso, C.R., Serafino, R., Kirby, M., Atwal, K.S. J. Med. Chem. (2001) [Pubmed]
  24. The Mycobacterium tuberculosis cmaA2 gene encodes a mycolic acid trans-cyclopropane synthetase. Glickman, M.S., Cahill, S.M., Jacobs, W.R. J. Biol. Chem. (2001) [Pubmed]
  25. Isodiiodomethane is the methylene transfer agent in cyclopropanation reactions with olefins using ultraviolet photolysis of diiodomethane in solutions: a density functional theory investigation of the reactions of isodiiodomethane, iodomethyl radical, and iodomethyl cation with ethylene. Phillips, D.L., Fang, W.H., Zheng, X. J. Am. Chem. Soc. (2001) [Pubmed]
  26. Oxidation-reduction chemistry of DL-alpha-lipoic acid, propanedithiol, and trimethylene disulfide in aprotic and in aqueous media. Howie, J.K., Houts, J.J., Sawyer, D.T. J. Am. Chem. Soc. (1977) [Pubmed]
  27. X-ray structure analysis and the intervalent electron transfer in organic mixed-valence crystals with bridged aromatic cation radicals. Lindeman, S.V., Rosokha, S.V., Sun, D., Kochi, J.K. J. Am. Chem. Soc. (2002) [Pubmed]
  28. Fluorocyclopropyl quinolones. 1. Synthesis and structure-activity relationships of 1-(2-fluorocyclopropyl)-3-pyridonecarboxylic acid antibacterial agents. Atarashi, S., Imamura, M., Kimura, Y., Yoshida, A., Hayakawa, I. J. Med. Chem. (1993) [Pubmed]
  29. Cloning, sequencing, mapping and hyperexpression of the ribC gene coding for riboflavin synthase of Escherichia coli. Eberhardt, S., Richter, G., Gimbel, W., Werner, T., Bacher, A. Eur. J. Biochem. (1996) [Pubmed]
  30. The influence of antiestrogens on pS2 and cathepsin D mRNA induction in MCF-7 breast cancer cells. Rajah, T.T., Dunn, S.T., Pento, J.T. Anticancer Res. (1996) [Pubmed]
  31. Fluorinated phenylcyclopropylamines. Part 4: effects of aryl substituents and stereochemistry on the inhibition of monoamine oxidases by 1-aryl-2-fluoro-cyclopropylamines. Ye, S., Yoshida, S., Fröhlich, R., Haufe, G., Kirk, K.L. Bioorg. Med. Chem. (2005) [Pubmed]
  32. Structure-activity relationship studies of CNS agents. Part 38. Novel 1,4-benzoxazin-3(4H)-one, 1,2-benzoxazolin-3-one and 1,3-benzoxazolin-2,4-dione arylpiperazine derivatives with different 5-HT1A and antagonistic 5-HT2A activities. Mokrosz, M.J., Kowalski, P., Kowalska, T., Majka, Z., Duszyńska, B., Bojarski, A.J., Fruziński, A., Karolak-Wojciechowska, J., Wesołowska, A., Kłodzińska, A., Tatarczyńska, E., Chojnacka-Wójcik, E. Arch. Pharm. (Weinheim) (1999) [Pubmed]
  33. Malignant hyperthermia triggered by cyclopropane during cesarean section. Lips, F.J., Newland, M., Dutton, G. Anesthesiology (1982) [Pubmed]
  34. Involvement of cyclopropane fatty acids in the response of Pseudomonas putida KT2440 to freeze-drying. Muñoz-Rojas, J., Bernal, P., Duque, E., Godoy, P., Segura, A., Ramos, J.L. Appl. Environ. Microbiol. (2006) [Pubmed]
  35. Letter: Deposits in cyclopropane flowmeter tubes. Bracken, A. British journal of anaesthesia. (1976) [Pubmed]
WikiGenes - Universities