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Chemical Compound Review

deoxyhypusine     (2S)-2-amino-6-(4- aminobutylamino)hexanoic...

Synonyms: AG-H-30369, CHEBI:50038, HMDB11150, AC1L3TXV, CTK3E9603, ...
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Disease relevance of deoxyhypusine

  • The recombinant enzyme formed upon expression in Escherichia coli effectively catalyzed deoxyhypusine synthesis [1].
  • Hydralazine, one of the most frequently prescribed drugs for the treatment of moderate to severe hypertension, added to the culture, resulted in the accumulation of a protein(s) containing the precursor amino acid deoxyhypusine [N epsilon-(4-aminobutyl)lysine] [2].

High impact information on deoxyhypusine

  • Purified recombinant yeast and human DOHH enzymes effectively catalyzed hydroxylation of the deoxyhypusine residue in the eIF5A intermediate [3].
  • This first structure of a deoxyhypusine synthase.NAD.inhibitor ternary complex under physiological conditions now provides a structural context to discuss the results of previous biochemical investigations of the deoxyhypusine synthase reaction mechanism [4].
  • No reversal was observed with [3H]hypusine protein, suggesting that hydroxylation at the 4-aminobutyl side chain of the deoxyhypusine residue prevents deoxyhypusine synthase-mediated reversal of the modification [5].
  • The synthesis of deoxyhypusine catalyzed by this enzyme involves transfer of the 4-aminobutyl moiety of spermidine to a specific lysine residue in the eIF5A precursor protein to form a deoxyhypusine-containing eIF5A intermediate, eIF5A(Dhp) [5].
  • Deoxyhypusine synthase from tobacco. cDNA isolation, characterization, and bacterial expression of an enzyme with extended substrate specificity [6].

Biological context of deoxyhypusine


Anatomical context of deoxyhypusine


Associations of deoxyhypusine with other chemical compounds


Gene context of deoxyhypusine

  • The results obtained thus far define the minimum domain of the eIF-5A precursor protein required for enzymatic deoxyhypusine synthesis as Phe30-Asp80, which corresponds to a region of high amino acid conservation in this protein throughout the eukaryotic kingdom [20].
  • Higher activity of recombinant bovine deoxyhypusine synthase vs. human deoxyhypusine synthase [9].
  • Activities of the enzyme from both human and bovine have been measured by their ability to convert the eIF5A precursor protein to the intermediate, deoxyhypusine form of eIF5A [9].
  • DHS mediates the first of two enzymatic reactions that activate eIF-5A by converting a conserved lysine to the unusual amino acid, deoxyhypusine [21].
  • Purified deoxyhypusine synthase catalyzes the overall synthesis of deoxyhypusine and, in the absence of the eIF-5A precursor, catalyzes the cleavage of spermidine [22].

Analytical, diagnostic and therapeutic context of deoxyhypusine


  1. Cloning and expression of human deoxyhypusine synthase cDNA. Structure-function studies with the recombinant enzyme and mutant proteins. Joe, Y.A., Wolff, E.C., Park, M.H. J. Biol. Chem. (1995) [Pubmed]
  2. Hydralazine inhibition of the post-translational hydroxylation of deoxyhypusine, a polyamine-derived amino acid. Paz, M.A., Torrelio, B.M., Gallop, P.M. Biochem. Pharmacol. (1984) [Pubmed]
  3. Molecular cloning, expression, and structural prediction of deoxyhypusine hydroxylase: a HEAT-repeat-containing metalloenzyme. Park, J.H., Aravind, L., Wolff, E.C., Kaevel, J., Kim, Y.S., Park, M.H. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  4. A new crystal structure of deoxyhypusine synthase reveals the configuration of the active enzyme and of an enzyme.NAD.inhibitor ternary complex. Umland, T.C., Wolff, E.C., Park, M.H., Davies, D.R. J. Biol. Chem. (2004) [Pubmed]
  5. Reversal of the deoxyhypusine synthesis reaction. Generation of spermidine or homospermidine from deoxyhypusine by deoxyhypusine synthase. Park, J.H., Wolff, E.C., Folk, J.E., Park, M.H. J. Biol. Chem. (2003) [Pubmed]
  6. Deoxyhypusine synthase from tobacco. cDNA isolation, characterization, and bacterial expression of an enzyme with extended substrate specificity. Ober, D., Hartmann, T. J. Biol. Chem. (1999) [Pubmed]
  7. Identification of YHR068w in Saccharomyces cerevisiae chromosome VIII as a gene for deoxyhypusine synthase. Expression and characterization of the enzyme. Kang, K.R., Wolff, E.C., Park, M.H., Folk, J.E., Chung, S.I. J. Biol. Chem. (1995) [Pubmed]
  8. Hypusine: its post-translational formation in eukaryotic initiation factor 5A and its potential role in cellular regulation. Park, M.H., Wolff, E.C., Folk, J.E. Biofactors (1993) [Pubmed]
  9. Higher activity of recombinant bovine deoxyhypusine synthase vs. human deoxyhypusine synthase. Huang, J.K., Tsai, S., Huang, G.H., Gowda, P.G., Walzer, A.M., Wen, L. Protein Expr. Purif. (2004) [Pubmed]
  10. Deoxyhypusine hydroxylase from rat testis. Partial purification and characterization. Abbruzzese, A., Park, M.H., Folk, J.E. J. Biol. Chem. (1986) [Pubmed]
  11. Antiproliferative effects of inhibitors of deoxyhypusine synthase. Inhibition of growth of Chinese hamster ovary cells by guanyl diamines. Park, M.H., Wolff, E.C., Lee, Y.B., Folk, J.E. J. Biol. Chem. (1994) [Pubmed]
  12. Evaluation of the metal ion requirement of the human deoxyhypusine hydroxylase from HeLa cells using a novel enzyme assay. Csonga, R., Ettmayer, P., Auer, M., Eckerskorn, C., Eder, J., Klier, H. FEBS Lett. (1996) [Pubmed]
  13. Deoxyhypusine synthase assay based on the use of polyhistidine-tagged substrate and metal chelate-affinity chromatography. Tao, Y., Skrenta, H.M., Chen, K.Y. Anal. Biochem. (1994) [Pubmed]
  14. Characterization and reconstitution of a cell free system for NAD(+)-dependent deoxyhypusine formation on the 18 kDa eIF-4D precursor. Dou, Q.P., Chen, K.Y. Biochim. Biophys. Acta (1990) [Pubmed]
  15. Comparison of the activities of variant forms of eIF-4D. The requirement for hypusine or deoxyhypusine. Park, M.H., Wolff, E.C., Smit-McBride, Z., Hershey, J.W., Folk, J.E. J. Biol. Chem. (1991) [Pubmed]
  16. Purification of deoxyhypusine synthase from Neurospora crassa to homogeneity by substrate elution affinity chromatography. Tao, Y., Chen, K.Y. J. Biol. Chem. (1995) [Pubmed]
  17. Enzyme-substrate intermediate at a specific lysine residue is required for deoxyhypusine synthesis. The role of Lys329 in human deoxyhypusine synthase. Joe, Y.A., Wolff, E.C., Lee, Y.B., Park, M.H. J. Biol. Chem. (1997) [Pubmed]
  18. Cell-free synthesis of deoxyhypusine. Separation of protein substrate and enzyme and identification of 1,3-diaminopropane as a product of spermidine cleavage. Park, M.H., Wolff, E.C. J. Biol. Chem. (1988) [Pubmed]
  19. Deoxyhypusine synthase generates and uses bound NADH in a transient hydride transfer mechanism. Wolff, E.C., Wolff, J., Park, M.H. J. Biol. Chem. (2000) [Pubmed]
  20. Structural features of the eIF-5A precursor required for posttranslational synthesis of deoxyhypusine. Joe, Y.A., Park, M.H. J. Biol. Chem. (1994) [Pubmed]
  21. Isolation and characterization of senescence-induced cDNAs encoding deoxyhypusine synthase and eucaryotic translation initiation factor 5A from tomato. Wang, T.W., Lu, L., Wang, D., Thompson, J.E. J. Biol. Chem. (2001) [Pubmed]
  22. Deoxyhypusine synthase from rat testis: purification and characterization. Wolff, E.C., Lee, Y.B., Chung, S.I., Folk, J.E., Park, M.H. J. Biol. Chem. (1995) [Pubmed]
  23. Interaction of eukaryotic initiation factor 5A with the human immunodeficiency virus type 1 Rev response element RNA and U6 snRNA requires deoxyhypusine or hypusine modification. Liu, Y.P., Nemeroff, M., Yan, Y.P., Chen, K.Y. Biol. Signals (1997) [Pubmed]
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