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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
MeSH Review


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Disease relevance of Hydrogenation

  • Trans isomers of fatty acids, formed by the partial hydrogenation of vegetable oils to produce margarine and vegetable shortening, increase the ratio of plasma low-density-lipoprotein to high-density-lipoprotein cholesterol, so it is possible that they adversely influence risk of coronary heart disease (CHD) [1].
  • The primary signal in the biological perception of temperature: Pd-catalyzed hydrogenation of membrane lipids stimulated the expression of the desA gene in Synechocystis PCC6803 [2].
  • Hydrogenation of cis-9,trans-11-octadecadienoic acid to yield trans-11-octadecenoic acid by cell-free preparations of Butyrivibrio fibrisolvens has been obtained under strictly anaerobic conditions [3].
  • The formal dehydration of two vicinal phenol moieties of p-tert-butylcalix[6]arene was achieved in two steps by mild oxidation of the calixarene followed by treatment of the resulting monospirodienone derivative (9c) with an ionic hydrogenation mixture (Et(3)SiH/CF(3)COOH) [4].
  • Initial hydrogenation during catabolism of picric acid by Rhodococcus erythropolis HL 24-2 [5].

Psychiatry related information on Hydrogenation

  • The diastereoisomer of III (VII), obtained by hydrogenation of the methobromide of I (IV), extrusion of methyl bromide, and O-demethylation of the resultant free base (VIII), was almost inactive antinociceptively and did not suppress withdrawal symptoms in morphine-dependent monkeys [6].
  • Platinum-oxide hydrogenation of 5-m-methoxyphenyl-2-methyl-9-oxomorphan (I) gave the 9 alpha-hydroxy racemate (II) whose phenolic analogue (III) is a strong antinociceptive agent, fully supportive of morphine dependence in rhesus monkeys [6].

High impact information on Hydrogenation

  • Here we report direct observations of the structure of supported metal clusters consisting of four iridium atoms, and the identification of hydrocarbon ligands bound to them during propene hydrogenation [7].
  • We propose a reaction mechanism whereby TrmE actively participates in the formylation reaction of uridine and regulates the ensuing hydrogenation reaction of a Schiff's base intermediate [8].
  • Although catalytic hydrogenation has been practiced for over a century, use of hydrogen as a terminal reductant in catalytic C-C bond formation has been restricted to processes involving migratory insertion of carbon monoxide, e.g., alkene hydroformylation and related Fischer-Tropsch-type reactions [9].
  • These catalysts have demonstrated their utility in the enantioselective hydrogenation of the tetrasubstituted cyclopentenone "dehydrodione", which leads to the commercially important perfume component Paradisone (Firmenich) [10].
  • The selective hydrogenations of polyenes (such as 1,5,9-cyclododecatriene and 2,5-norbornadiene) are especially efficient [11].

Chemical compound and disease context of Hydrogenation


Biological context of Hydrogenation

  • Reductive alkylation of proteins using iridium catalyzed transfer hydrogenation [17].
  • Kinetics and mechanism of N2 hydrogenation in bis(cyclopentadienyl) zirconium complexes and dinitrogen functionalization by 1,2-addition of a saturated C-H bond [18].
  • Similar one-pot esterifications and hydrogenations by sol-gel entrapped lipase and heterogenized rhodium complexes were carried out successfully with the saturated nonoic, undecanoic, and lauric acids together with several saturated and unsaturated alcohols [19].
  • In the first phase metathesis-mediated dimerization of an aminodeoxymonosaccharide which was either allylated at the anomeric center or at C4 led to E/Z mixtures of C2-symmetric homodimers which were transformed into the corresponding 1,4-butanediol linked disaccharides by catalytic hydrogenation of the central olefinic double bond [20].
  • [reaction: see text] A one-pot tandem cross-metathesis/hydrogenation/cyclization procedure was achieved at room temperature, under 1 atm of hydrogen, in the presence of a ruthenium catalyst and PtO(2) showing the compatibility of the two catalysts [21].

Anatomical context of Hydrogenation


Associations of Hydrogenation with chemical compounds

  • Hydrogen atoms emerging from the bulk of Ni metal to the surface are observed to be the reactive species in the hydrogenation of adsorbed methyl radical, ethylene, and acetylene to gas-phase products [26].
  • Phase separation of the constituents of catalytic systems eliminated substrate inhibition (hydrogenation of aldehydes) and helped formation of catalytically active species ([RhH(PPh(3))(3)] from [RhCl(PPh(3))(3)] in hydrogenation of acetophenone) [27].
  • Intradendrimer hydrogenation and carbon-carbon coupling reactions in water, organic solvents, biphasic fluorous/organic solvents, and supercritical CO2 are also described [28].
  • The diphosphine ligand was found to be highly effective in the asymmetric hydrogenation of alpha- and beta-ketoesters, 2-(6'-methoxy-2'-naphthyl)propenoic acid, beta-(acylamino)acrylates, and enol acetates [29].
  • (ii) The koff for NADH from its GPDH complex is 60 sec-1 rather than 9.4 sec-1 in Tris.HCl buffer (pH 7.4) at 25 degrees C. With this value one can explain kcat = 50 sec-1 for LDH-catalyzed hydrogenation of pyruvate with GPDH-bound NADH as coenzyme [30].

Gene context of Hydrogenation


Analytical, diagnostic and therapeutic context of Hydrogenation


  1. Intake of trans fatty acids and risk of coronary heart disease among women. Willett, W.C., Stampfer, M.J., Manson, J.E., Colditz, G.A., Speizer, F.E., Rosner, B.A., Sampson, L.A., Hennekens, C.H. Lancet (1993) [Pubmed]
  2. The primary signal in the biological perception of temperature: Pd-catalyzed hydrogenation of membrane lipids stimulated the expression of the desA gene in Synechocystis PCC6803. Vigh, L., Los, D.A., Horváth, I., Murata, N. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  3. Biohydrogenation of unsaturated fatty acids. Hydrogenation by cell-free preparations of Butyrivibrio fibrisolvens. Hunter, W.J., Baker, F.C., Rosenfeld, I.S., Keyser, J.B., Tove, S.B. J. Biol. Chem. (1976) [Pubmed]
  4. Intramolecular AR--O--AR bond formation in calixarenes. Agbaria, K., Biali, S.E. J. Org. Chem. (2001) [Pubmed]
  5. Initial hydrogenation during catabolism of picric acid by Rhodococcus erythropolis HL 24-2. Lenke, H., Knackmuss, H.J. Appl. Environ. Microbiol. (1992) [Pubmed]
  6. 9 alpha- and 9 beta-Hydroxyphenylmorphans. Awaya, H., May, E.L., Jacobson, A.E., Aceto, M.D. Journal of pharmaceutical sciences. (1984) [Pubmed]
  7. Observation of ligand effects during alkene hydrogenation catalysed by supported metal clusters. Argo, A.M., Odzak, J.F., Lai, F.S., Gates, B.C. Nature (2002) [Pubmed]
  8. The structure of the TrmE GTP-binding protein and its implications for tRNA modification. Scrima, A., Vetter, I.R., Armengod, M.E., Wittinghofer, A. EMBO J. (2005) [Pubmed]
  9. Catalytic C-C bond formation via capture of hydrogenation intermediates. Jang, H.Y., Krische, M.J. Acc. Chem. Res. (2004) [Pubmed]
  10. Asymmetric catalytic hydrogenation. Design of new Ru catalysts and chiral ligands: from laboratory to industrial applications. Genet, J.P. Acc. Chem. Res. (2003) [Pubmed]
  11. High-performance nanocatalysts for single-step hydrogenations. Thomas, J.M., Johnson, B.F., Raja, R., Sankar, G., Midgley, P.A. Acc. Chem. Res. (2003) [Pubmed]
  12. Synthesis of pregnenoic acid derivatives possessing structural elements of prostaglandins. Wicha, J., Bal, K. Steroids (1977) [Pubmed]
  13. Stimulation of the anaerobic growth of Salmonella typhimurium by reduction of L-carnitine, carnitine derivatives and structure-related trimethylammonium compounds. Seim, H., Löster, H., Claus, R., Kleber, H.P., Strack, E. Arch. Microbiol. (1982) [Pubmed]
  14. Enzymic glycosylation of (+/-)-(3,5/4,6)-3,6-diazido-4,5- dihydroxycyclohexene. A way to prepare stereochemically pure and enzyme resistant, basic pseudo-disaccharides as competitive enzyme inhibitors. Lehmann, J., Rob, B. Carbohydr. Res. (1995) [Pubmed]
  15. Properties of two Clostridia strains acting as catalysts for the preparative stereospecific hydrogenation of 2-enoic acids and 2-alken-1-ols with hydrogen gas. Bader, J., Günther, H., Rambeck, B., Simon, H. Hoppe-Seyler's Z. Physiol. Chem. (1978) [Pubmed]
  16. Substrate specificity of Streptomyces beta-xylanase toward glucoxylan. Yoshida, S., Satoh, T., Shimokawa, S., Oku, T., Ito, T., Kusakabe, I. Biosci. Biotechnol. Biochem. (1994) [Pubmed]
  17. Reductive alkylation of proteins using iridium catalyzed transfer hydrogenation. McFarland, J.M., Francis, M.B. J. Am. Chem. Soc. (2005) [Pubmed]
  18. Kinetics and mechanism of N2 hydrogenation in bis(cyclopentadienyl) zirconium complexes and dinitrogen functionalization by 1,2-addition of a saturated C-H bond. Bernskoetter, W.H., Lobkovsky, E., Chirik, P.J. J. Am. Chem. Soc. (2005) [Pubmed]
  19. One-pot sequences of reactions with sol-gel entrapped opposing reagents: an enzyme and metal-complex catalysts. Gelman, F., Blum, J., Avnir, D. J. Am. Chem. Soc. (2002) [Pubmed]
  20. First preparation of spacer-linked cyclic neooligoaminodeoxysaccharides. Chen, G.W., Kirschning, A. Chemistry (Weinheim an der Bergstrasse, Germany) (2002) [Pubmed]
  21. Tandem cross-metathesis/hydrogenation/cyclization reactions by using compatible catalysts. Cossy, J., Bargiggia, F., BouzBouz, S. Org. Lett. (2003) [Pubmed]
  22. Relationship between lipid saturation and lipid-protein interaction in liver mitochondria modified by catalytic hydrogenation with reference to cardiolipin molecular species. Schlame, M., Horvàth, L., Vìgh, L. Biochem. J. (1990) [Pubmed]
  23. Modulation of chloroplast membrane lipids by homogeneous catalytic hydrogenation. Vigh, L., Joó, F., Droppa, M., Horváth, L.I., Horváth, G. Eur. J. Biochem. (1985) [Pubmed]
  24. Regio- and stereoselective hydrogenation of 2'-demethoxy-2'-methyldehydrogriseofulvin, a symmetrical substrate, to (+)-2'-demethoxy-2'-methylgriseofulvin with a cell-free system of Streptomyces cinereocrocatus. Oda, T., Hashimoto, H., Sato, Y. Chem. Pharm. Bull. (1990) [Pubmed]
  25. The fatty acyl chain composition of human normal and leukaemic lymphocytes and its modulation by specialised hydrogenation. Peel, W.E., Thomson, A.E. Leuk. Res. (1983) [Pubmed]
  26. The unique chemistry of hydrogen beneath the surface: catalytic hydrogenation of hydrocarbons. Ceyer, S.T. Acc. Chem. Res. (2001) [Pubmed]
  27. Aqueous biphasic hydrogenations. Joó, F. Acc. Chem. Res. (2002) [Pubmed]
  28. Dendrimer-encapsulated metal nanoparticles: synthesis, characterization, and applications to catalysis. Crooks, R.M., Zhao, M., Sun, L., Chechik, V., Yeung, L.K. Acc. Chem. Res. (2001) [Pubmed]
  29. Remarkably diastereoselective synthesis of a chiral biphenyl diphosphine ligand and its application in asymmetric hydrogenation. Qiu, L., Wu, J., Chan, S., Au-Yeung, T.T., Ji, J.X., Guo, R., Pai, C.C., Zhou, Z., Li, X., Fan, Q.H., Chan, A.S. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  30. Reexamination of the kinetics of the transfer of NADH between its complexes with glycerol-3-phosphate dehydrogenase and with lactate dehydrogenase. Chock, P.B., Gutfreund, H. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  31. Cationic reduction of bastadin-4 to bastadin-5. Preparation of 5-[2h]-bastadin-5 by site-specific isotopic labeling. Masuno, M.N., Molinski, T.F. J. Nat. Prod. (2003) [Pubmed]
  32. Uric acid is a major antioxidant in human nasal airway secretions. Peden, D.B., Hohman, R., Brown, M.E., Mason, R.T., Berkebile, C., Fales, H.M., Kaliner, M.A. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  33. Heat of hydrogenation of 1,5-dehydroquadricyclane. A computational and experimental study of a highly pyramidalized alkene. Hoenigman, R.L., Kato, S., Bierbaum, V.M., Borden, W.T. J. Am. Chem. Soc. (2005) [Pubmed]
  34. Asymmetric hydrogenation of tert-alkyl ketones. Ohkuma, T., Sandoval, C.A., Srinivasan, R., Lin, Q., Wei, Y., Muñiz, K., Noyori, R. J. Am. Chem. Soc. (2005) [Pubmed]
  35. A succession of isomers of ruthenium dihydride complexes. Which one is the ketone hydrogenation catalyst? Abbel, R., Abdur-Rashid, K., Faatz, M., Hadzovic, A., Lough, A.J., Morris, R.H. J. Am. Chem. Soc. (2005) [Pubmed]
  36. Biosynthesis of the unsaturated 14-carbon fatty acids found on the N termini of photoreceptor-specific proteins. DeMar, J.C., Wensel, T.G., Anderson, R.E. J. Biol. Chem. (1996) [Pubmed]
  37. NMR imaging of the distribution of the liquid phase in a catalyst pellet during alpha-methylstyrene evaporation accompanied by its vapor-phase hydrogenation. Koptyug, I.V., Kulikov, A.V., Lysova, A.A., Kirillov, V.A., Parmon, V.N., Sagdeev, R.Z. J. Am. Chem. Soc. (2002) [Pubmed]
  38. Abnormal ligand binding and reversible ring hydrogenation in the reaction of imidazolium salts with IrH(5)(PPh(3))(2). Gründemann, S., Kovacevic, A., Albrecht, M., Faller, J.W., Crabtree, R.H. J. Am. Chem. Soc. (2002) [Pubmed]
  39. Identification of novel nonmethylene-interrupted fatty acids, 7E,13E-20:2, 7E,13E,17Z-20:3, 9E,15E,19Z-22:3, and 4Z,9E,15E,19Z-22:4, in Ophiuroidea (brittle star) lipids. Sato, D., Ando, Y., Tsujimoto, R., Kawasaki, K. Lipids (2001) [Pubmed]
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