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Chemical Compound Review

CHEMBL49917     (E)-4-(6-aminopurin-9-yl)but- 2-en-1-ol

Synonyms: trans isomer, CHEBI:172587, AC1O5QS2, 9-(4-Hydroxy-2-buten-1-yl)adenine, 9-(trans-4-Hydroxy-2-buten-1-yl)adenine
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Disease relevance of trans isomer


High impact information on trans isomer

  • This EFE activity displays similar characteristics to EFE found in plant tissue: it converts the trans isomer of the ACC analogue 1-amino-2-ethylcyclopropane-1-carboxylic acid to 1-butene in preference to the cis isomer, and it is strongly inhibited by cobaltous ions and 1,10-phenanthroline [6].
  • The trans-isomer of tubulozole (tubulozole-T, R 48 265), which has no antitumor activity in vivo, did not affect the microtubule system of cells in vitro or their capacity for directional migration or for malignant invasion [7].
  • Modeling suggests steric hindrance at the active site as the determinant of the weak inhibiting potency of the trans isomer [8].
  • The major cisplatin-damaged DNA-binding proteins of 26.5 and 28 kDa recognized adducts of DNA modified with cisplatin but not with its trans-isomer or with UV radiation [9].
  • The bromo enol lactone trans isomer 2a was found to be a very effective inhibitor of HLE and chymotrypsin, as shown by the binding constants (KI), acylation rates (ka), inactivation rates, and partition ratios determined for each enzyme [10].

Chemical compound and disease context of trans isomer


Biological context of trans isomer


Anatomical context of trans isomer


Associations of trans isomer with other chemical compounds

  • X-ray analysis of the trans isomer showed an axial disposition of the phenyl ring; however, NMR studies suggest that this conformation is fixed in the trans isomer, but not in the cis [24].
  • It was found that N-(3-aminopropyl)-1,4-diamino-cis-but-2-ene [the cis isomer of the alkene analogue of spermidine] was a good substrate for spermine synthase, but that the trans isomer [N-(3-aminopropyl)-1,4-diamino-trans-but-2-ene] and the alkene analogue [N-(3-aminopropyl)-1,4-diaminobut-2-yne] were not substrates [25].
  • Carbonyl ene cyclization of aldehydes 4a-e catalyzed by MeAlCl(2) in refluxing chloroform afforded the trans piperidines 7a-e with diastereomeric ratios of up to 93:7, while aldehyde 4f afforded solely the cis product 6f, which was resistant to isomerization to the trans isomer [26].
  • We identified the zeatin isolated as the trans isomer by HPLC and by a radioimmunoassay in which monoclonal antibodies specific for trans-hydroxylated cytokinins were used [27].
  • BACKGROUND: Cis-urocanic acid (cis-UCA), formed from the naturally occurring trans-isomer in the epidermis on ultraviolet (UV) radiation, initiates some of the changes leading to UV-induced immunosuppression, but its role in cutaneous carcinogenesis has not been fully investigated [28].

Gene context of trans isomer

  • Despite trans isomer specificity of ERK2, a doubly phosphorylated RNase T1 was found as the final reaction product [29].
  • However, in the case of 1-(cyclopropylmethyl)-N-n-propyl analogs, the trans isomer has a slightly higher 5-HT1A affinity than its cis counterpart [30].
  • The trans isomer is able to form two good hydrogen bonds, with G13 on the same strand and A7 on the opposite strand [31].
  • Compared to liposomes, DMPC in the complexes has more acyl chain trans isomers at temperatures above 24 degrees C; at temperatures above ca. 30 degrees C, trans isomer content is about the same for complexes and liposomes [32].
  • The trans isomer was found to be more favorable than cis isomer by only 0.6 kcal/mol [33].

Analytical, diagnostic and therapeutic context of trans isomer


  1. The substrate-binding site in Escherichia coli cyclophilin A preferably recognizes a cis-proline isomer or a highly distorted form of the trans isomer. Konno, M., Ito, M., Hayano, T., Takahashi, N. J. Mol. Biol. (1996) [Pubmed]
  2. Regulation of platinum-compound cytotoxicity by the c-Jun N-terminal kinase and c-Jun signaling pathway in small-cell lung cancer cells. Levresse, V., Marek, L., Blumberg, D., Heasley, L.E. Mol. Pharmacol. (2002) [Pubmed]
  3. Synthesis and antimetastatic properties of stereoisomeric tricyclic bis(dioxopiperazines) in the Lewis lung carcinoma model. Witiak, D.T., Nair, R.V., Schmid, F.A. J. Med. Chem. (1985) [Pubmed]
  4. Cytotoxicity, DNA strand breakage and DNA-protein crosslinking by a novel transplatinum compound in human A2780 ovarian and MCF-7 breast carcinoma cells. Farrell, N., Povirk, L.F., Dange, Y., DeMasters, G., Gupta, M.S., Kohlhagen, G., Khan, Q.A., Pommier, Y., Gewirtz, D.A. Biochem. Pharmacol. (2004) [Pubmed]
  5. Pharmacokinetics of high-dose oral CCNU in bone marrow transplant patients. Kastrissios, H., Chao, N.J., Blaschke, T.F. Cancer Chemother. Pharmacol. (1996) [Pubmed]
  6. Identification of a tomato gene for the ethylene-forming enzyme by expression in yeast. Hamilton, A.J., Bouzayen, M., Grierson, D. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  7. Effects of tubulozole on the microtubule system of cells in culture and in vivo. Geuens, G.M., Nuydens, R.M., Willebrords, R.E., Van de Veire, R.M., Goossens, F., Dragonetti, C.H., Mareel, M.M., De Brabander, M.J. Cancer Res. (1985) [Pubmed]
  8. Structural basis for the inhibition of the biosynthesis of biotin by the antibiotic amiclenomycin. Sandmark, J., Mann, S., Marquet, A., Schneider, G. J. Biol. Chem. (2002) [Pubmed]
  9. Purification of nuclear proteins that bind to cisplatin-damaged DNA. Identity with high mobility group proteins 1 and 2. Hughes, E.N., Engelsberg, B.N., Billings, P.C. J. Biol. Chem. (1992) [Pubmed]
  10. Proline-valine pseudo peptide enol lactones. Effective and selective inhibitors of chymotrypsin and human leukocyte elastase. Reed, P.E., Katzenellenbogen, J.A. J. Biol. Chem. (1991) [Pubmed]
  11. G2/M cell cycle arrest and induction of apoptosis by a stilbenoid, 3,4,5-trimethoxy-4'-bromo-cis-stilbene, in human lung cancer cells. Lee, E.J., Min, H.Y., Joo Park, H., Chung, H.J., Kim, S., Nam Han, Y., Lee, S.K. Life Sci. (2004) [Pubmed]
  12. A subchronic study of the toxicity of an orally administered benzoquinolizinyl derivative in the rat and dog. Hartnagel, R.E., Phillips, B.M., Kraus, P.J., Kowalski, R.L., Fonseca, E.H. Toxicology (1975) [Pubmed]
  13. Solid and solution NMR studies of the complexation of Ag(+) with the trans isomer of captopril: Biological activities of this high blood pressure drug along with its Ag(+) complex. Isab, A.A., Wazeer, M.I. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. (2006) [Pubmed]
  14. Direct NMR evidence that prolidase is specific for the trans isomer of imidodipeptide substrates. King, G.F., Middlehurst, C.R., Kuchel, P.W. Biochemistry (1986) [Pubmed]
  15. The mechanism of activation of 4-hydroxycyclophosphamide. Borch, R.F., Millard, J.A. J. Med. Chem. (1987) [Pubmed]
  16. Light-induced anticancer activity of [RuCl2(DMSO)4] complexes. Brindell, M., Kuliś, E., Elmroth, S.K., Urbańska, K., Stochel, G. J. Med. Chem. (2005) [Pubmed]
  17. G-G base-pairing in nucleobase adducts of the anticancer drug cis-[PtCl2(NH3)(2-picoline)] and its trans isomer. McGowan, G., Parsons, S., Sadler, P.J. Chemistry (Weinheim an der Bergstrasse, Germany) (2005) [Pubmed]
  18. Effects of a trans isomer of arachidonic acid on rat platelet aggregation and eicosanoid production. Berdeaux, O., Chardigny, J.M., Sébédio, J.L., Mairot, T., Poullain, D., Vatèle, J.M., Noël, J.P. J. Lipid Res. (1996) [Pubmed]
  19. Excretion of cefprozil into human breast milk. Shyu, W.C., Shah, V.R., Campbell, D.A., Venitz, J., Jaganathan, V., Pittman, K.A., Wilber, R.B., Barbhaiya, R.H. Antimicrob. Agents Chemother. (1992) [Pubmed]
  20. Modification of DNA dynamics by platinum drug binding: a time-dependent fluorescence depolarization study of the interaction of cis- and trans-diamminedichloroplatinum(II) with DNA. Millar, D.P., Ho, K.M., Aroney, M.J. Biochemistry (1988) [Pubmed]
  21. Investigation of 4-(3-hydroxyphenyl)-4-methylpipecolic acid as a conformationally restricted mimic of the tyrosyl residue of leucine-enkephalinamide. Sugg, E.E., Portoghese, P.S. J. Med. Chem. (1986) [Pubmed]
  22. Effect of doxepin on uptake and efflux of serotonin human blood patelets in vitro. Lingjaerde, O. Psychopharmacologia. (1976) [Pubmed]
  23. Trans-2-en-valproic acid limits action potential firing frequency in mouse central neurons in cell culture. Wamil, A.W., Loscher, W., McLean, M.J. J. Pharmacol. Exp. Ther. (1997) [Pubmed]
  24. Synthesis, conformation, and dopaminergic activity of 5,6-ethano-bridged derivatives of selective dopaminergic 3-benzazepines. Weinstock, J., Oh, H.J., DeBrosse, C.W., Eggleston, D.S., Wise, M., Flaim, K.E., Gessner, G.W., Sawyer, J.L., Kaiser, C. J. Med. Chem. (1987) [Pubmed]
  25. Role of unsaturated derivatives of spermidine as substrates for spermine synthase and in supporting growth of SV-3T3 cells. Pegg, A.E., Nagarajan, S., Naficy, S., Ganem, B. Biochem. J. (1991) [Pubmed]
  26. Synthesis of 3,4-disubstituted piperidines by carbonyl ene and prins cyclizations: switching between kinetic and thermodynamic control with Brønsted and Lewis acid catalysts. Williams, J.T., Bahia, P.S., Kariuki, B.M., Spencer, N., Philp, D., Snaith, J.S. J. Org. Chem. (2006) [Pubmed]
  27. tRNA is the source of low-level trans-zeatin production in Methylobacterium spp. Koenig, R.L., Morris, R.O., Polacco, J.C. J. Bacteriol. (2002) [Pubmed]
  28. Urocanic acid isomers in patients with non-melanoma skin cancer. De Simone, C., Masini, C., Cattaruzza, M.S., Guerriero, C., Cerimele, D., Norval, M. Br. J. Dermatol. (2001) [Pubmed]
  29. Catalysis of proline-directed protein phosphorylation by peptidyl-prolyl cis/trans isomerases. Weiwad, M., Werner, A., Rücknagel, P., Schierhorn, A., Küllertz, G., Fischer, G. J. Mol. Biol. (2004) [Pubmed]
  30. Centrally acting serotonergic agents. Synthesis and structure-activity relationships of C-1- or C-3-substituted derivatives of 8-hydroxy-2-(di-n-propylamino)tetralin. Lin, C.H., Haadsma-Svensson, S.R., Lahti, R.A., McCall, R.B., Piercey, M.F., Schreur, P.J., VonVoigtlander, P.F., Chidester, C.G. J. Med. Chem. (1993) [Pubmed]
  31. Solution structure of N-(2-deoxy-D-erythro-pentofuranosyl)urea frameshifts, one intrahelical and the other extrahelical, by nuclear magnetic resonance and molecular dynamics. Gervais, V., Cognet, J.A., Guy, A., Cadet, J., Téoule, R., Fazakerley, G.V. Biochemistry (1998) [Pubmed]
  32. Raman spectroscopy of the thermal properties of reassembled high-density lipoprotein: apolipoprotein A-I complexes of dimyristoylphosphatidylcholine. Gilman, T., Kauffman, J.W., Pownall, H.J. Biochemistry (1981) [Pubmed]
  33. Ab initio study of the structures and stabilities of the dimer of ethyl cation, (C(2)H(+)(5))(2) and related C(4)H(10)(2+) isomers. Olah, G.A., Prakash, G.K., Rasul, G. J. Org. Chem. (2001) [Pubmed]
  34. Pharmacokinetics and tissue penetration of ceftibuten. Wise, R., Nye, K., O'Neill, P., Wostenholme, M., Andrews, J.M. Antimicrob. Agents Chemother. (1990) [Pubmed]
  35. Location of double bonds in monounsaturated fatty acids of Campylobacter cryaerophila with dimethyl disulfide derivatives and combined gas chromatography-mass spectrometry. Moss, C.W., Lambert-Fair, M.A. J. Clin. Microbiol. (1989) [Pubmed]
  36. Practical synthesis of a neuropeptide Y antagonist via stereoselective addition to a ketene. Iida, T., Satoh, H., Maeda, K., Yamamoto, Y., Asakawa, K., Sawada, N., Wada, T., Kadowaki, C., Itoh, T., Mase, T., Weissman, S.A., Tschaen, D., Krska, S., Volante, R.P. J. Org. Chem. (2005) [Pubmed]
  37. Specific synthesis and stereochemical assignment of the diastereomeric 3,5-O-benzylidene-1,2-O-isopropylidene-alpha-D-glucofuranose isomers. Akerfeldt, K., Bartlett, P.A. Carbohydr. Res. (1986) [Pubmed]
  38. Simultaneous monitoring of dopamine, its metabolites and trans-isomer of atypical neuroleptic drug carbidine concentrations in striatal dialysates of conscious rats. Gainetdinov, R.R., Sotnikova, T.D., Grekhova, T.V., Rayevsky, K.S. Prog. Neuropsychopharmacol. Biol. Psychiatry (1996) [Pubmed]
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