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Chemical Compound Review

Isoleucine     (2S,3S)-2-amino-3-methyl- pentanoic acid

Synonyms: Isoleucina, Isoleucinum, Polyisoleucine, L-Ile, iso-leucine, ...
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Disease relevance of Isoleucine


Psychiatry related information on Isoleucine


High impact information on Isoleucine


Chemical compound and disease context of Isoleucine


Biological context of Isoleucine

  • Case I states that liganding of the activator sites must percede substrate-binding at the active site, and Case II states that the activator site liganding is required solely for reactivation of the L-isoleucine-inhibited enzyme [17].
  • Studies on the biosynthesis of paraherquamide: concerning the mechanism of the oxidative cyclization of L-isoleucine to beta-methylproline [18].
  • In the presence of L-leucine or L-isoleucine, however, which both inhibited L-NNA uptake, the IC50 of L-NNA was increased from 1.2 microM to 37 microM but the inhibitory actions of L-NMA remained unaffected [19].
  • Acylation of the (hydroxethyl)hydrazine dipeptide isostere with the L-tert-leucine derivative 29 increased the oral bioavailability significantly when compared to the corresponding L-valine or L-isoleucine derivatives [20].
  • In order to identify the system responsible for L-isoleucine export, we have used transposon mutagenesis to isolate mutants of C. glutamicum sensitive to the peptide isoleucyl-isoleucine [4].

Anatomical context of Isoleucine


Associations of Isoleucine with other chemical compounds


Gene context of Isoleucine


Analytical, diagnostic and therapeutic context of Isoleucine


  1. Isoleucyl initiator tRNA does not initiate eucaryotic protein synthesis. Wagner, T., Gross, M., Sigler, P.B. J. Biol. Chem. (1984) [Pubmed]
  2. A controlled trial of amino acid therapy in amyotrophic lateral sclerosis: I. Clinical, functional, and maximum isometric torque data. Tandan, R., Bromberg, M.B., Forshew, D., Fries, T.J., Badger, G.J., Carpenter, J., Krusinski, P.B., Betts, E.F., Arciero, K., Nau, K. Neurology (1996) [Pubmed]
  3. Significance of L-alloisoleucine in plasma for diagnosis of maple syrup urine disease. Schadewaldt, P., Bodner-Leidecker, A., Hammen, H.W., Wendel, U. Clin. Chem. (1999) [Pubmed]
  4. Export of L-isoleucine from Corynebacterium glutamicum: a two-gene-encoded member of a new translocator family. Kennerknecht, N., Sahm, H., Yen, M.R., Pátek, M., Saier Jr, M.H., Eggeling, L. J. Bacteriol. (2002) [Pubmed]
  5. Frequency-pulsed electron capture gas-liquid chromatographic analysis of metabolites produced by Clostridium difficile in broth enriched with amino acids. Brooks, J.B., Nunez-Montiel, O.L., Wycoff, B.J., Moss, C.W. J. Clin. Microbiol. (1984) [Pubmed]
  6. Diagnosis of maple syrup urine disease by determination of L-valine, L-isoleucine, L-leucine and L-phenylalanine in neonatal blood spots by gas chromatography-mass spectrometry. Deng, C., Deng, Y. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. (2003) [Pubmed]
  7. Structural basis for double-sieve discrimination of L-valine from L-isoleucine and L-threonine by the complex of tRNA(Val) and valyl-tRNA synthetase. Fukai, S., Nureki, O., Sekine, S., Shimada, A., Tao, J., Vassylyev, D.G., Yokoyama, S. Cell (2000) [Pubmed]
  8. Enzyme structure with two catalytic sites for double-sieve selection of substrate. Nureki, O., Vassylyev, D.G., Tateno, M., Shimada, A., Nakama, T., Fukai, S., Konno, M., Hendrickson, T.L., Schimmel, P., Yokoyama, S. Science (1998) [Pubmed]
  9. Prevention of methotrexate cytotoxicity by asparaginase inhibition of methotrexate polyglutamate formation. Jolivet, J., Cole, D.E., Holcenberg, J.S., Poplack, D.G. Cancer Res. (1985) [Pubmed]
  10. Identification of a novel system L amino acid transporter structurally distinct from heterodimeric amino acid transporters. Babu, E., Kanai, Y., Chairoungdua, A., Kim, d.o. .K., Iribe, Y., Tangtrongsup, S., Jutabha, P., Li, Y., Ahmed, N., Sakamoto, S., Anzai, N., Nagamori, S., Endou, H. J. Biol. Chem. (2003) [Pubmed]
  11. Purification and characterization of NAD:Penicillamine ADP transferase from Bacillus sphaericus. A novel NAD-dependent enzyme catalyzing phosphoramide bond formation. Yanagidani, J., Tamura, T., Inagaki, K., Soda, K., Tanaka, H. J. Biol. Chem. (1999) [Pubmed]
  12. Nonprotein amino acid furanomycin, unlike isoleucine in chemical structure, is charged to isoleucine tRNA by isoleucyl-tRNA synthetase and incorporated into protein. Kohno, T., Kohda, D., Haruki, M., Yokoyama, S., Miyazawa, T. J. Biol. Chem. (1990) [Pubmed]
  13. NMR analyses of the conformations of L-isoleucine and L-valine bound to Escherichia coli isoleucyl-tRNA synthetase. Kohda, D., Kawai, G., Yokoyama, S., Kawakami, M., Mizushima, S., Miyazawa, T. Biochemistry (1987) [Pubmed]
  14. Labelling of L-isoleucine tRNA ligase from Escherichia coli with L-isoleucyl-bromomethyl ketone. Rainey, P., Holler, E., Kula, M.R. Eur. J. Biochem. (1976) [Pubmed]
  15. Construction of L-lysine-, L-threonine-, and L-isoleucine-overproducing strains of Corynebacterium glutamicum. Sahm, H., Eggeling, L., Eikmanns, B., Krämer, R. Ann. N. Y. Acad. Sci. (1996) [Pubmed]
  16. A comparative study of essential arginine residues in Gramicidin S synthetase 2 and isoleucyl tRNA synthetase. Kanda, M., Hori, K., Miura, S., Yamada, Y., Saito, Y. J. Biochem. (1982) [Pubmed]
  17. Threonine deaminase from Salmonella typhimurium. Relationship between regulatory sites. Decedue, C.J., Hofler, J.G., Burns, R.O. J. Biol. Chem. (1975) [Pubmed]
  18. Studies on the biosynthesis of paraherquamide: concerning the mechanism of the oxidative cyclization of L-isoleucine to beta-methylproline. Stocking, E.M., Martinez, R.A., Silks, L.A., Sanz-Cervera, J.F., Williams, R.M. J. Am. Chem. Soc. (2001) [Pubmed]
  19. Characterization of endothelial cell amino acid transport systems involved in the actions of nitric oxide synthase inhibitors. Schmidt, K., Klatt, P., Mayer, B. Mol. Pharmacol. (1993) [Pubmed]
  20. New aza-dipeptide analogues as potent and orally absorbed HIV-1 protease inhibitors: candidates for clinical development. Bold, G., Fässler, A., Capraro, H.G., Cozens, R., Klimkait, T., Lazdins, J., Mestan, J., Poncioni, B., Rösel, J., Stover, D., Tintelnot-Blomley, M., Acemoglu, F., Beck, W., Boss, E., Eschbach, M., Hürlimann, T., Masso, E., Roussel, S., Ucci-Stoll, K., Wyss, D., Lang, M. J. Med. Chem. (1998) [Pubmed]
  21. Interaction of branched chain amino acids and keto acids upon pancreatic islet metabolism and insulin secretion. Hutton, J.C., Sener, A., Malaisse, W.J. J. Biol. Chem. (1980) [Pubmed]
  22. Piperine-mediated changes in the permeability of rat intestinal epithelial cells. The status of gamma-glutamyl transpeptidase activity, uptake of amino acids and lipid peroxidation. Johri, R.K., Thusu, N., Khajuria, A., Zutshi, U. Biochem. Pharmacol. (1992) [Pubmed]
  23. Interrelation between the metabolism of L-isoleucine and L-allo-isoleucine in patients with maple syrup urine disease. Wendel, U., Langenbeck, U., Seakins, J.W. Pediatr. Res. (1989) [Pubmed]
  24. Incorporation of 15N from L-leucine into isoleucine by rat brain cerebral cortex slices. Gheorvassaki, E., Papadakis, D., Alikaridis, F., Kephalas, T., Larsen, C., Palaiologos, G. J. Neurosci. Res. (1992) [Pubmed]
  25. Effect of taurine on alteration in adrenal functions induced by stress. Nakagawa, K., Kuriyama, K. Jpn. J. Pharmacol. (1975) [Pubmed]
  26. Leucine transport in Escherichia coli. The resolution of multiple transport systems and their coupling to metabolic energy. Wood, J.M. J. Biol. Chem. (1975) [Pubmed]
  27. In vitro activity and in vivo efficacy of icofungipen (PLD-118), a novel oral antifungal agent, against the pathogenic yeast Candida albicans. Hasenoehrl, A., Galic, T., Ergovic, G., Marsic, N., Skerlev, M., Mittendorf, J., Geschke, U., Schmidt, A., Schoenfeld, W. Antimicrob. Agents Chemother. (2006) [Pubmed]
  28. Response of rainbow trout (Oncorhynchus mykiss) to supplements of individual essential amino acids in a semipurified diet, including an estimate of the maintenance requirement for essential amino acids. Rodehutscord, M., Becker, A., Pack, M., Pfeffer, E. J. Nutr. (1997) [Pubmed]
  29. 2-Methylbutyryl-coenzyme A dehydrogenase deficiency: a new inborn error of L-isoleucine metabolism. Gibson, K.M., Burlingame, T.G., Hogema, B., Jakobs, C., Schutgens, R.B., Millington, D., Roe, C.R., Roe, D.S., Sweetman, L., Steiner, R.D., Linck, L., Pohowalla, P., Sacks, M., Kiss, D., Rinaldo, P., Vockley, J. Pediatr. Res. (2000) [Pubmed]
  30. Calcium triggers beta-defensin (hBD-2 and hBD-3) and chemokine macrophage inflammatory protein-3 alpha (MIP-3alpha/CCL20) expression in monolayers of activated human keratinocytes. Pernet, I., Reymermier, C., Guezennec, A., Branka, J.E., Guesnet, J., Perrier, E., Dezutter-Dambuyant, C., Schmitt, D., Viac, J. Exp. Dermatol. (2003) [Pubmed]
  31. Linking central metabolism with increased pathway flux: L-valine accumulation by Corynebacterium glutamicum. Radmacher, E., Vaitsikova, A., Burger, U., Krumbach, K., Sahm, H., Eggeling, L. Appl. Environ. Microbiol. (2002) [Pubmed]
  32. Effects of an Escherichia coli ilvA mutant gene encoding feedback-resistant threonine deaminase on L-isoleucine production by Brevibacterium flavum. Hashiguchi, K., Kojima, H., Sato, K., Sano, K. Biosci. Biotechnol. Biochem. (1997) [Pubmed]
  33. Identification and sequence determination of the acetohydroxy acid isomeroreductase gene from Brevibacterium flavum MJ233. Inui, M., Vertès, A.A., Kobayashi, M., Kurusu, Y., Yukawa, H. DNA Seq. (1993) [Pubmed]
  34. L-Leucine-induced secretion of glucagon and insulin, and the "off-response" to L-leucine in vitro. I. Characterization of the dynamics of secretion. Pek, S., Santiago, J.C., Tai, T.Y. Endocrinology (1978) [Pubmed]
  35. The random coil goes to beta transition of copolymers of L-lysine and L-isoleucine: potentiometric titration and circular dischroism studies. Walter, B., Fasman, G.D. Biopolymers (1977) [Pubmed]
  36. Effect of intravenous L-isoleucine infusion upon concentration of free isoleucine in milk. Popescu, O., Allison, M.J., Brown, R.W. J. Dairy Sci. (1976) [Pubmed]
  37. E.S.R. of spin-trapped radicals in gamma-irradiated polycrystalline amino acids. Chromatographic separation of radicals. Makino, K., Riesz, P. Int. J. Radiat. Biol. Relat. Stud. Phys. Chem. Med. (1982) [Pubmed]
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