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Chemical Compound Review

SureCN5547     cyclopropanamine

Synonyms: AGN-PC-0D4TKW, AG-K-49961, ACMC-209p4d, CHEBI:34660, ANW-36827, ...
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Disease relevance of cyclopropanamine

  • Cyclopropylamine is a mechanism-based inhibitor of the quinoprotein methylamine dehydrogenase (MADH) from Paracoccus denitrificans [1].
  • As part of an effort to understand the role of this enzyme in PGPR, the genes for ACC deaminase from two PGPR, Enterobacter cloacae CAL2 and UW4, have been isolated [2].
  • These genes are highly homologous to the ACC deaminase genes from Pseudomonas strains 6G5 and F17 and similar to the ACC deaminase gene from Pseudomonas sp. strain ACP [2].
  • In this research, to produce double-stranded (ds)RNA of tomato ACC oxidase, we linked the sense and antisense configurations of DNA fragments with 1,002-bp or 7-nt artificially synthesized fragments, respectively, and then placed these under the control of a modified cauliflower mosaic virus 35S promoter [3].
  • Carnation cuttings treated with non-transformed and 1-aminocyclopropane (ACC) deaminase-containing Azospirillum brasilense Cd1843 produced significantly more roots than untreated controls and fewer roots than cuttings treated with 0.1% indolebutyric acid (IBA) [4].

High impact information on cyclopropanamine

  • Cyclopropylamine, lacking the benzene moiety of TCP, inhibited lysyl oxidase irreversibly and competitively, and was not a substrate, pointing toward a defining role for the benzene moiety in the interaction of TCP with lysyl oxidase [5].
  • The synthetic and analytical methods developed in the course of these studies should facilitate the application of cyclopropylamine-containing probes to reactions catalyzed by cytochrome P450 enzymes [6].
  • Aminocyclopropane carboxylic Acid synthase is a regulated step in ethylene-dependent induced conifer defense. Full-length cDNA cloning of a multigene family, differential constitutive, and wound- and insect-induced expression, and cellular and subcellular localization in spruce and douglas fir [7].
  • Preincubation of DGD with ACC, like the exchange of Na+ for K+, shifts the conformational distribution, in agreement with the steady-state kinetics [8].
  • A possible explanation of drug resistance based on the observation of suicide inactivation of bacterial cytochrome P-450 by the cyclopropylamine moiety has also been proposed and is discussed in this report [9].

Biological context of cyclopropanamine


Anatomical context of cyclopropanamine


Associations of cyclopropanamine with other chemical compounds


Gene context of cyclopropanamine

  • The 2A6 protein shows three domains that are highly conserved among E8, ACC oxidases, and 2-ODDs [18].
  • The minimum onset energy of photoionization of cyclopropylamine was calculated to be 201.5 kcal/mol (CCSD(T)) compared to experimental values of between about 201 and 204 kcal/mol [19].


  1. Inter-subunit cross-linking of methylamine dehydrogenase by cyclopropylamine requires residue alphaPhe55. Sun, D., Davidson, V.L. FEBS Lett. (2002) [Pubmed]
  2. Isolation and characterization of ACC deaminase genes from two different plant growth-promoting rhizobacteria. Shah, S., Li, J., Moffatt, B.A., Glick, B.R. Can. J. Microbiol. (1998) [Pubmed]
  3. Different effects on ACC oxidase gene silencing triggered by RNA interference in transgenic tomato. Xiong, A.S., Yao, Q.H., Peng, R.H., Li, X., Han, P.L., Fan, H.Q. Plant Cell Rep. (2005) [Pubmed]
  4. The effect of native and ACC deaminase-containing Azospirillum brasilense Cd1843 on the rooting of carnation cuttings. Li, Q., Saleh-Lakha, S., Glick, B.R. Can. J. Microbiol. (2005) [Pubmed]
  5. Reaction of lysyl oxidase with trans-2-phenylcyclopropylamine. Shah, M.A., Trackman, P.C., Gallop, P.M., Kagan, H.M. J. Biol. Chem. (1993) [Pubmed]
  6. N-dealkylation of an N-cyclopropylamine by horseradish peroxidase. Fate of the cyclopropyl group. Shaffer, C.L., Morton, M.D., Hanzlik, R.P. J. Am. Chem. Soc. (2001) [Pubmed]
  7. Aminocyclopropane carboxylic Acid synthase is a regulated step in ethylene-dependent induced conifer defense. Full-length cDNA cloning of a multigene family, differential constitutive, and wound- and insect-induced expression, and cellular and subcellular localization in spruce and douglas fir. Ralph, S.G., Hudgins, J.W., Jancsik, S., Franceschi, V.R., Bohlmann, J. Plant Physiol. (2007) [Pubmed]
  8. Coexisting kinetically distinguishable forms of dialkylglycine decarboxylase engendered by alkali metal ions. Zhou, X., Kay, S., Toney, M.D. Biochemistry (1998) [Pubmed]
  9. In vitro anti-Mycobacterium avium activities of quinolones: predicted active structures and mechanistic considerations. Klopman, G., Li, J.Y., Wang, S., Pearson, A.J., Chang, K., Jacobs, M.R., Bajaksouzian, S., Ellner, J.J. Antimicrob. Agents Chemother. (1994) [Pubmed]
  10. Use of a tomato mutant constructed with reverse genetics to study fruit ripening, a complex developmental process. Theologis, A., Oeller, P.W., Wong, L.M., Rottmann, W.H., Gantz, D.M. Dev. Genet. (1993) [Pubmed]
  11. Changes in gene expression in canola roots induced by ACC-deaminase-containing plant-growth-promoting bacteria. Hontzeas, N., Saleh, S.S., Glick, B.R. Mol. Plant Microbe Interact. (2004) [Pubmed]
  12. Expression and internal feedback regulation of ACC synthase and ACC oxidase genes in ripening tomato fruit. Nakatsuka, A., Shiomi, S., Kubo, Y., Inaba, A. Plant Cell Physiol. (1997) [Pubmed]
  13. The influence of inverted repeats on the production of small antisense RNAs involved in gene silencing. Han, Y., Grierson, D. Mol. Genet. Genomics (2002) [Pubmed]
  14. 1-aminocyclopropane-1-carboxylate (ACC) deaminase induced by ACC synthesized and accumulated in Penicillium citrinum intracellular spaces. Jia, Y.J., Ito, H., Matsui, H., Honma, M. Biosci. Biotechnol. Biochem. (2000) [Pubmed]
  15. Inhibition by cyclopropylamine of the quinoprotein methylamine dehydrogenase is mechanism-based and causes covalent cross-linking of alpha and beta subunits. Davidson, V.L., Jones, L.H. Biochemistry (1991) [Pubmed]
  16. Electron paramagnetic resonance study of the mononuclear Al species formed in the reaction of Al atoms and cyclopropylamine at 77 k in an adamantane matrix. Joly, H.A., Ashley, J., Levesque, M.Y., Rank, J.P. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2006) [Pubmed]
  17. Wound-induced ethylene synthesis and expression and formation of 1-aminocyclopropane-1-carboxylate (ACC) synthase, ACC oxidase, phenylalanine ammonia-lyase, and peroxidase in wounded mesocarp tissue of Cucurbita maxima. Kato, M., Hayakawa, Y., Hyodo, H., Ikoma, Y., Yano, M. Plant Cell Physiol. (2000) [Pubmed]
  18. Analysis of Arabidopsis cDNA that shows homology to the tomato E8 cDNA. Trentmann, S.M., Kende, H. Plant Mol. Biol. (1995) [Pubmed]
  19. Molecular orbital calculations of ring opening of the isoelectronic cyclopropylcarbinyl radical, cyclopropoxy radical, and cyclopropylaminium radical cation series of radical clocks. Cooksy, A.L., King, H.F., Richardson, W.H. J. Org. Chem. (2003) [Pubmed]
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