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Chemical Compound Review

lysinate     2,6-diaminohexanoate

Synonyms: AC1NUTWT, lysine anion, lys(-), CHEBI:32563
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Disease relevance of lysine

  • Each of 23 EBV isolates analyzed from this population were also mutated in the EBNA4 416-424 epitope, the mutations selectively involving one of the two anchor residues in positions 2 (417 val-leu) or 9 (424 lys-asp, -arg or -thr) that are critical for A11-peptide interaction [1].
  • A model for the structure and expression of the colicin E1 operon is proposed in which the cea and lys genes are expressed from a single inducible promoter that is controlled by the lexA repressor in response to the SOS system of Escherichia coli [2].
  • To test the mutagenic and lethal effects of mate infusion, caffeine, hyperthermia, and their combinations, we used Saccharomyces cerevisiae as an eucaryotic model system measuring lys to LYS reversions [3].
  • Various types of plaque-forming or defective phages which transduce hisA or lys marker at considerably high frequencies were thus obtained [4].
  • A chromosomal segment containing several genetic markers, from metB to thyA, near the replication terminus is associated with the membranous structure of Bacillus subtilis, but markers adjacent to this region, lys, ura, and metC, are not [5].

High impact information on lysine

  • The mutation resulted in a single amino acid substitution of glu to lys at residue 227 of the alpha 3 domain [6].
  • Replacement of lys 622 in the ATP binding domain of P100gag-mil abolishes the in vitro autophosphorylation of the protein and the biological properties of the v-mil oncogene of MH2 virus [7].
  • The results suggest that a serine protease with lys and arg ester bond specificity is involved in the control of sperm motility [8].
  • We analyzed the structural and functional relationships among independently cloned segments of the plasmid ColE1 region that regulates and codes for colicin E1 (cea), immunity (imm), and the mitomycin C-induced lethality function (lys) [2].
  • On the basis of physiological properties, restriction endonuclease mapping, and DNA sequence analysis, the following recombinant plasmids were determined to represent three major functional classes: pNP12 (cea+, imm+, lys+), pNP4 (cea+, imm+, lys-), and pNP6 (cea+, imm-, lys-) [2].

Chemical compound and disease context of lysine


Biological context of lysine

  • Our results have established the order, boundaries, and relative orientation of the three structural genes, the location of the promoter region for imm gene transcription, and the predicted amino acid sequences of the imm and lys gene products [2].
  • Red cell survival was measured in ten subjects with S-C disease and one with S-O Arab (alpha 2 beta 2-121 glu yields lys) disease using both DF32p and 51Cr as tags [13].
  • Exogenous lysine is the regulatory signal for lys gene expression and specifically serves as a ligand for LysM by altering its DNA binding affinity [14].
  • Nucleotide sequence of the structural genes for the mitochondrial asp, lys, ser-tRNAs from chicken [15].
  • This new gene of Mu has been named 'lig'. A 5 kb fragment responsible for the reported effects and localized between genes gam and lys of Mu genome has been cloned in pBR322 [16].

Anatomical context of lysine


Associations of lysine with other chemical compounds

  • ATP-driven proton pumping activity is lost with the substitution of lys, ile, val, or glu for arginine 210 [21].
  • Both of the genes from Blackhawk contained length polymorphisms that result in omission of some of the repeat units (pro pro val tyr lys) from the proteins [22].
  • Most H1 histones contain repeated motifs in their C-terminal domain, and these form part of an octapeptide (ser pro lys lys ala lys lys pro) that is highly conserved in many H1 histone proteins [23].
  • Analysis of each point mutation by marker rescue demonstrated that mutations gly to asp at residue 80, pro to phe at 458, lys to asn at 484, and ile to val at 485 conferred the resistance phenotype, while the mutation changing ser to leu at 176 did not affect the rifampicin phenotype [24].
  • Bioavailability of racemic ibuprofen and its lysinate from suppositories in rabbits [25].

Gene context of lysine

  • An asn to lys polymorphism in the third intracellular loop of the human alpha 2A-adrenergic receptor imparts enhanced agonist-promoted Gi coupling [26].
  • We have purified peptides matching the highly conserved motif Pro-X-(Asp/glu)-X-X-(Lys/Arg)-X-(Arg/lys) (X is an unspecified amino acid) of the triplicate gene structure sequence of the beef heart PTP [27].
  • Nucleotide sequencing of a 1,735-bp DNA fragment revealed two adjacent coding regions of 342 bp (hol) and 951 bp (lys) in the same reading frame which appear to belong to a common transcriptional unit [28].
  • We find that one substitution mutation (lys 61 to glu) alters the selectivity of VDAC [29].
  • Based on the comparison of the B. subtilis lysA sequence with a sequence of the DAP-decarboxylase gene cloned into pUB110 (Yamamoto et al., Nucleic Acids Res., 17, 10105 (1989], it was found that the lys gene in the plasmid was fused with the dnaN gene in its COOH-terminal region [30].

Analytical, diagnostic and therapeutic context of lysine

  • The glu80 to lys mutation results in a transport-defective phenotype and a mature protein that migrates abnormally slowly on nonreduced SDS-PAGE, but normally under reducing conditions; this was confirmed by site-directed mutagenesis and expression in vitro [31].
  • Northern blot analysis of total RNA isolated 30 min after heat induction of Mu cts lysogens demonstrated that the full-length lys and P transcripts were approximately 7.6 and 6.3 kb long, respectively [32].
  • Only non-O-glycosylated N-POMC1-77 and O-glycosylated N-POMC1-77 with truncated oligosaccharide sidechains were sensitive to cleavage and generated predominantly lys-gamma 3-melanotropin, identified by high-performance liquid chromatography [33].
  • The lysin-encoding lys gene was verified by PCR amplification from the total phage DNA and subcloned [34].
  • It is shown here by functional studies and by immunoblotting with anti-PLP antibodies that transmembrane gradients of anions determine the availability of a 35-kD fragment lys residue to surface labeling by PLP, in analogy with their effects on labeling of 65-kD fragment by DS [35].


  1. T cell responses and virus evolution: loss of HLA A11-restricted CTL epitopes in Epstein-Barr virus isolates from highly A11-positive populations by selective mutation of anchor residues. de Campos-Lima, P.O., Levitsky, V., Brooks, J., Lee, S.P., Hu, L.F., Rickinson, A.B., Masucci, M.G. J. Exp. Med. (1994) [Pubmed]
  2. Structural and functional organization of the colicin E1 operon. Waleh, N.S., Johnson, P.H. Proc. Natl. Acad. Sci. U.S.A. (1985) [Pubmed]
  3. Mutagenicity induced by hyperthermia, hot mate infusion, and hot caffeine in Saccharomyces cerevisiae. Candreva, E.C., Keszenman, D.J., Barrios, E., Gelós, U., Nunes, E. Cancer Res. (1993) [Pubmed]
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  6. The Lyt-2 molecule recognizes residues in the class I alpha 3 domain in allogeneic cytotoxic T cell responses. Connolly, J.M., Potter, T.A., Wormstall, E.M., Hansen, T.H. J. Exp. Med. (1988) [Pubmed]
  7. Replacement of lys 622 in the ATP binding domain of P100gag-mil abolishes the in vitro autophosphorylation of the protein and the biological properties of the v-mil oncogene of MH2 virus. Denhez, F., Heimann, B., d'Auriol, L., Graf, T., Coquillaud, M., Coll, J., Galibert, F., Moelling, K., Stehelin, D., Ghysdael, J. EMBO J. (1988) [Pubmed]
  8. Effects of protease inhibitors and substrates on motility of mammalian spermatozoa. de Lamirande, E., Gagnon, C. J. Cell Biol. (1986) [Pubmed]
  9. Microbiology, safety, and pharmacokinetics of aztreonam lysinate for inhalation in patients with cystic fibrosis. Gibson, R.L., Retsch-Bogart, G.Z., Oermann, C., Milla, C., Pilewski, J., Daines, C., Ahrens, R., Leon, K., Cohen, M., McNamara, S., Callahan, T.L., Markus, R., Burns, J.L. Pediatr. Pulmonol. (2006) [Pubmed]
  10. Construction of a novel gene bank of Bacillus subtilis using a low copy number vector in Escherichia coli. Hasnain, S., Thomas, C.M. J. Gen. Microbiol. (1986) [Pubmed]
  11. Effect of a single dose of ibuprofen lysinate before embryo transfer on pregnancy rates in cows. Elli, M., Gaffuri, B., Frigerio, A., Zanardelli, M., Covini, D., Candiani, M., Vignali, M. Reproduction (2001) [Pubmed]
  12. Study of an artificial endoassociation between Saccharomyces cerevisiae and Escherichia coli. González, M.T., Martin, I., Guerra, I., Montoya, E. Microbios (1987) [Pubmed]
  13. Red cell life span in sickle cell-hemoglobin C disease with a note about sickle cell-hemoglobin O ARAB. McCurdy, P.R., Mahmood, L., Sherman, A.S. Blood (1975) [Pubmed]
  14. The Sulfolobus solfataricus Lrp-like protein LysM regulates lysine biosynthesis in response to lysine availability. Brinkman, A.B., Bell, S.D., Lebbink, R.J., de Vos, W.M., van der Oost, J. J. Biol. Chem. (2002) [Pubmed]
  15. Nucleotide sequence of the structural genes for the mitochondrial asp, lys, ser-tRNAs from chicken. Lee, Y.H., Liaw, L.L., Yung, T.T., Lo, S.J. Nucleic Acids Res. (1989) [Pubmed]
  16. Restoration of ligase activity in E. coli K12 lig ts7 strain by bacteriophage Mu and cloning of a DNA fragment harbouring the Mu 'lig' gene. Ghelardini, P., Paolozzi, L., Liebart, J.C. Nucleic Acids Res. (1980) [Pubmed]
  17. A chimera of the cytoplasmic tail of the mannose 6-phosphate/IGF-II receptor and lysozyme localizes to the TGN rather than prelysosomes where the bulk of the endogenous receptor is found. Conibear, E., Pearse, B.M. J. Cell. Sci. (1994) [Pubmed]
  18. Isolation and characterization of the lysozyme-encoding gene from the silkworm Bombyx mori. Lee, W.J., Brey, P.T. Gene (1995) [Pubmed]
  19. Cloning, sequence analysis, and expression of the genes encoding lytic functions of Bacteriophage phi g1e. Oki, M., Kakikawa, M., Yamada, K., Taketo, A., Kodaira, K.I. Gene (1996) [Pubmed]
  20. Transcriptional regulation of the lysozyme gene in airway gland serous cells. Kai, H., Takeuchi, K., Ohmori, H., Li, J.D., Gallup, M., Basbaum, C. J. Cell. Biochem. (1996) [Pubmed]
  21. Proton translocation by the F1F0ATPase of Escherichia coli. Mutagenic analysis of the a subunit. Cain, B.D., Simoni, R.D. J. Biol. Chem. (1989) [Pubmed]
  22. Genetic length polymorphisms create size variation in proline-rich proteins of the cell wall. Schmidt, J.S., Lindstrom, J.T., Vodkin, L.O. Plant J. (1994) [Pubmed]
  23. A highly conserved sequence in H1 histone genes as an oligonucleotide hybridization probe: isolation and sequence of a duck H1 gene. Tönjes, R., Doenecke, D. J. Mol. Evol. (1987) [Pubmed]
  24. Mutations in ORF D13L and other genetic loci alter the rifampicin phenotype of vaccinia virus. McNulty-Kowalczyk, A., Paoletti, E. Virology (1993) [Pubmed]
  25. Bioavailability of racemic ibuprofen and its lysinate from suppositories in rabbits. Hermann, T.W., Gtówka, F.K., Garrett, E.R. Journal of pharmaceutical sciences. (1993) [Pubmed]
  26. An asn to lys polymorphism in the third intracellular loop of the human alpha 2A-adrenergic receptor imparts enhanced agonist-promoted Gi coupling. Small, K.M., Forbes, S.L., Brown, K.M., Liggett, S.B. J. Biol. Chem. (2000) [Pubmed]
  27. Mitochondrial phosphate transport. N-ethylmaleimide insensitivity correlates with absence of beef heart-like Cys42 from the Saccharomyces cerevisiae phosphate transport protein. Guérin, B., Bukusoglu, C., Rakotomanana, F., Wohlrab, H. J. Biol. Chem. (1990) [Pubmed]
  28. Primary structure and functional analysis of the lysis genes of Lactobacillus gasseri bacteriophage phi adh. Henrich, B., Binishofer, B., Bläsi, U. J. Bacteriol. (1995) [Pubmed]
  29. Probing the structure of the mitochondrial channel, VDAC, by site-directed mutagenesis: a progress report. Blachly-Dyson, E., Peng, S.Z., Colombini, M., Forte, M. J. Bioenerg. Biomembr. (1989) [Pubmed]
  30. Molecular cloning and analysis of nucleotide sequence of the Bacillus subtilis lysA gene region using B. subtilis phage vectors and a multi-copy plasmid, pUB110. Yamamoto, J., Shimizu, M., Yamane, K. Agric. Biol. Chem. (1991) [Pubmed]
  31. Characterization of two new point mutations in the low density lipoprotein receptor genes of an English patient with homozygous familial hypercholesterolemia. Webb, J.C., Sun, X.M., Patel, D.D., McCarthy, S.N., Knight, B.L., Soutar, A.K. J. Lipid Res. (1992) [Pubmed]
  32. Identification and characterization of the terminators of the lys and P transcripts of bacteriophage Mu. Zha, J., Zhao, Z., Howe, M.M. J. Bacteriol. (1994) [Pubmed]
  33. Differential glycosylation of N-POMC1-77 regulates the production of gamma 3-MSH by purified pro-opiomelanocortin converting enzyme. A possible mechanism for tissue-specific processing. Birch, N.P., Estivariz, F.E., Bennett, H.P., Loh, Y.P. FEBS Lett. (1991) [Pubmed]
  34. Mur-LH, the broad-spectrum endolysin of Lactobacillus helveticus temperate bacteriophage phi-0303. Deutsch, S.M., Guezenec, S., Piot, M., Foster, S., Lortal, S. Appl. Environ. Microbiol. (2004) [Pubmed]
  35. Transport domain of the erythrocyte anion exchange protein. Bar-Noy, S., Cabantchik, Z.I. J. Membr. Biol. (1990) [Pubmed]
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