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Chemical Compound Review

Arginyllysine     (2S)-6-amino-2-[[(2S)-2- amino-5...

Synonyms: Arg-Lys, Arginyl-Lysine, L-Arg-L-Lys, CHEMBL380024, AG-F-45676, ...
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Disease relevance of Arg-Lys

  • The amino acid sequence in this region (Gly-29 Lys Lys Arg Ser Lys Ala) is similar to the nuclear location signal in simian virus 40 large T antigen (Pro-126 Lys Lys Lys Arg Lys Val) (D. Kalderon, B.L. Roberts, W.D. Richardson, and A.E. Smith, Cell 39:499-509, 1984) [1].
  • In this paper, we report a systematic comparison of the effects of positively (Arg, Lys, His) as well as negatively (Asp, Glu) charged residues on the membrane topology of a model Escherichia coli inner membrane protein [2].
  • An Arg/Lys-rich core peptide mimics TRBP binding to the HIV-1 TAR RNA upper-stem/loop [3].
  • The distinct Arg/Lys-rich and Met-rich region at positions 10-36 of the PLA2 homolog presumably are involved in its heparin-binding and the cell membrane-interference leading to edema and myotoxicity [4].
  • An Arg-Lys insertion at the hemagglutinin cleavage site of an H5N2 avian influenza isolate [5].

High impact information on Arg-Lys

  • The cDNA sequence reveals a long open reading frame (ORF) of 1773 nucleotides, with a putative nuclear targeting signal (Glu Arg Arg Lys Lys Lys Thr) at the extreme carboxyl terminus and an internal histidine (His)-rich region with a repeated conserved amino acid sequence between His pairs [6].
  • It was previously shown that the mRNA for the cat-1 Arg/Lys transporter is translated from an internal ribosome entry site (IRES) that is regulated by cellular stress [7].
  • Protein methylation plays a central role in both of these fields, as several different residues (Arg, Lys, Gln) are methylated in cells and methylation plays a central role in the "histone code" that regulates chromatin structure and impacts transcription [8].
  • The Sld2 protein has a cluster of 11 cyclin-dependent kinase (CDK) phosphorylation motifs (Ser/Thr-Pro), six of which match the canonical sequences Ser/Thr-Pro-X-Lys/Arg, Lys/Arg-Ser/Thr-Pro and Ser/Thr-Pro-Lys/Arg [9].
  • Sea urchin sperm-specific histones H1 and H2B have distinctive N-terminal, and in the case of H1 also C-terminal, domains containing repeats of a basic motif (-Ser-Pro-Lys/Arg-Lys/Arg- or a closely related sequence) [10].

Biological context of Arg-Lys

  • The DNA sequence of the mutant predicts the alteration of Lys 128----Thr within the sequence 127 Lys Lys Lys Arg Lys 131 of large T [11].
  • Semi-random cassette mutagenesis was used to generate mutants with replacements of residues 164-167 by Arg, Lys, Ser, or Asn [12].
  • The Arg-Lys sequence at positions 25-31, which resembles the binding site of apolipoprotein E, may mediate the high affinity binding of lactoferrin and block the binding of beta-VLDL to the remnant receptor with high efficiency [13].
  • The BD peptide also contains novel structural features such as a predicted Asx bend or "hook" at its amino-terminal end and laterally projecting cationic Arg/Lys side chains or "bristles" which may contribute to the binding properties of the HMG-I proteins [14].
  • We mutated His(73) in yeast actin to Arg, Lys, Ala, Gln, and Glu and detected no altered phenotypes associated with the mutations in vivo [15].

Anatomical context of Arg-Lys

  • An Arg-Lys esteropeptidase that converts somatostatin-28 in vitro into somatostatin-14 was previously characterized in extracts of rat cerebral cortex [16].
  • A seven residue peptide containing residues 368-374, Val Tyr Tyr Val Gly Arg Lys, was demonstrated to be capable of inducing chemotactic migration of human peripheral blood neutrophils, monocytes, monocyte leukemia cell line THP-1, and infant foreskin fibroblasts [17].
  • Recent experiments have shown that Arg, Lys, and Leu can be incorporated posttranslationally into proteins of regenerating sciatic nerves of rats [18].
  • Basic charge motifs, such as the BBB, BXXBB, and BBXXB motifs in alpha-helical integral membrane proteins, are significantly more frequent near cytoplasmic membrane surface than expected from the Arg/Lys (B) frequency [19].
  • Protein phosphorylation in neutrophils was monitored with two phosphospecific antibodies (pAbs) [termed pPKC(S1) Ab and pPKC(S2) Ab] that recognize products of protein kinase C (PKC) and other Arg/Lys-directed Ser/Thr protein kinases [20].

Associations of Arg-Lys with other chemical compounds

  • Mutations of the invariant Tyr(10) with either hydrophobic (Ala), aromatic (Phe), or positively charged (Arg, Lys) residues yielded Ca(V)beta 3-responsive whole cell currents, whereas mutations with negatively charged residues (Asp, Glu) disrupted Ca(V)beta 3 binding and modulation [21].
  • We demonstrated previously that two type II metacaspases of Arabidopsis thaliana, AtMC4 and AtMC9 are Arg/Lys-specific cysteine-dependent proteases [22].
  • This architectural arrangement apparently couples directional A-form duplex binding, by a hydrogen-bonding Arg-Lys phosphate ruler motif, to substrate-discrimination, by a tyrosine finger motif, thereby providing substrate-specific catalytic activity [23].
  • Setting the stage for new catalytic functions in designed proteins--exploring the imine pathway in the efficient decarboxylation of oxaloacetate by an Arg-Lys site in a four-helix bundle protein scaffold [24].
  • Since then, seven PCs have so far been discovered that cleave at the carboxy-terminal of a basic amino acid characterized by the consensus sequence Arg/Lys/His-X-X/Lys/Arg-Arg downward arrow, where X denotes any amino acid other than Cys [25].

Gene context of Arg-Lys

  • The primary translation product consists of 178 amino acid residues containing a putative signal sequence, a transmembrane domain, the mature BTC domain and a cytoplasmic domain containing a highly hydrophilic Arg-Lys-rich region similar to that of mouse BTC and human BTC [26].
  • On the basis of microsomal enzyme activities from heterozygotes, CYP1A1*1/2A, CYP1A1*1/2B, CYP1A1*1/4, and AHR(554) Arg/Lys variants do not appear to significantly affect CYP1A1 activities in human lung, and we observed no association between CYP1A1 activity and the GSTM1-null polymorphism [27].
  • A distinct, Arg/Lys-rich N-terminal region targets CKA1 to the cell periphery [28].
  • These studies have revealed that the amino acid sequence of human cardiac alpha tropomyosin is identical to that of the rabbit skeletal alpha tropomyosin, but for a single conservative substitution of Arg/Lys at position 220 [29].
  • Comparison of their N-terminal sequences showed 30% nonidentity over the first 35 amino acids, and comparison of their amino acid compositions demonstrated a marked difference in their Arg/Lys ratios, which was approximately 1 for chymase and 10 for cathepsin G [30].

Analytical, diagnostic and therapeutic context of Arg-Lys

  • Peptide mapping provided additional proof that p17 is a fragment which comprises the entire FK506 binding domain I of chicken hsp56, terminating with an Arg-Lys which might represent a processing site [31].
  • HPLC analysis of peptide fragments produced, followed by their amino acid analysis, revealed that the enzyme preferentially hydrolyzed the Arg-Arg or Arg-Lys bonds in dynorphins A 1-10, 1-9, and 1-8, beta-neoendorphin, adenorphin, and neurotensin [32].


  1. Amino acid sequences that determine the nuclear localization of yeast histone 2B. Moreland, R.B., Langevin, G.L., Singer, R.H., Garcea, R.L., Hereford, L.M. Mol. Cell. Biol. (1987) [Pubmed]
  2. Different positively charged amino acids have similar effects on the topology of a polytopic transmembrane protein in Escherichia coli. Andersson, H., Bakker, E., von Heijne, G. J. Biol. Chem. (1992) [Pubmed]
  3. An Arg/Lys-rich core peptide mimics TRBP binding to the HIV-1 TAR RNA upper-stem/loop. Erard, M., Barker, D.G., Amalric, F., Jeang, K.T., Gatignol, A. J. Mol. Biol. (1998) [Pubmed]
  4. Phospholipases A2 from Callosellasma rhodostoma venom gland cloning and sequencing of 10 of the cDNAs, three-dimensional modelling and chemical modification of the major isozyme. Tsai, I.H., Wang, Y.M., Au, L.C., Ko, T.P., Chen, Y.H., Chu, Y.F. Eur. J. Biochem. (2000) [Pubmed]
  5. An Arg-Lys insertion at the hemagglutinin cleavage site of an H5N2 avian influenza isolate. Perdue, M.L., Garcia, M., Beck, J., Brugh, M., Swayne, D.E. Virus Genes (1996) [Pubmed]
  6. xlgv7: a maternal gene product localized in nuclei of the central nervous system in Xenopus laevis. Miller, M., Kloc, M., Reddy, B., Eastman, E., Dreyer, C., Etkin, L. Genes Dev. (1989) [Pubmed]
  7. Ribosome stalling regulates IRES-mediated translation in eukaryotes, a parallel to prokaryotic attenuation. Fernandez, J., Yaman, I., Huang, C., Liu, H., Lopez, A.B., Komar, A.A., Caprara, M.G., Merrick, W.C., Snider, M.D., Kaufman, R.J., Lamers, W.H., Hatzoglou, M. Mol. Cell (2005) [Pubmed]
  8. Structural and sequence motifs of protein (histone) methylation enzymes. Cheng, X., Collins, R.E., Zhang, X. Annual review of biophysics and biomolecular structure. (2005) [Pubmed]
  9. A CDK-catalysed regulatory phosphorylation for formation of the DNA replication complex Sld2-Dpb11. Tak, Y.S., Tanaka, Y., Endo, S., Kamimura, Y., Araki, H. EMBO J. (2006) [Pubmed]
  10. Phosphorylation at clustered -Ser-Pro-X-Lys/Arg- motifs in sperm-specific histones H1 and H2B. Hill, C.S., Packman, L.C., Thomas, J.O. EMBO J. (1990) [Pubmed]
  11. The abnormal location of cytoplasmic SV40 large T is not caused by failure to bind to DNA or to p53. Paucha, E., Kalderon, D., Richardson, W.D., Harvey, R.W., Smith, A.E. EMBO J. (1985) [Pubmed]
  12. Anthrax toxin protective antigen is activated by a cell surface protease with the sequence specificity and catalytic properties of furin. Klimpel, K.R., Molloy, S.S., Thomas, G., Leppla, S.H. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  13. Removal of 14 N-terminal amino acids of lactoferrin enhances its affinity for parenchymal liver cells and potentiates the inhibition of beta- very low density lipoprotein binding. Ziere, G.J., Bijsterbosch, M.K., van Berkel, T.J. J. Biol. Chem. (1993) [Pubmed]
  14. The A.T-DNA-binding domain of mammalian high mobility group I chromosomal proteins. A novel peptide motif for recognizing DNA structure. Reeves, R., Nissen, M.S. J. Biol. Chem. (1990) [Pubmed]
  15. His(73), often methylated, is an important structural determinant for actin. A mutagenic analysis of HIS(73) of yeast actin. Yao, X., Grade, S., Wriggers, W., Rubenstein, P.A. J. Biol. Chem. (1999) [Pubmed]
  16. The somatostatin-28 convertase of rat brain cortex is associated with secretory granule membranes. Gomez, S., Gluschankof, P., Morel, A., Cohen, P. J. Biol. Chem. (1985) [Pubmed]
  17. Identification of a chemotactic epitope in human transforming growth factor-beta 1 spanning amino acid residues 368-374. Postlethwaite, A.E., Seyer, J.M. J. Cell. Physiol. (1995) [Pubmed]
  18. Amino acid modification of proteins in regenerating sciatic nerves of rats. Chakraborty, G., Yu, M., Luo, D., Sturman, J.A., Ingoglia, N.A. J. Neurosci. Res. (1990) [Pubmed]
  19. Basic charge clusters and predictions of membrane protein topology. Juretić, D., Zoranić, L., Zucić, D. Journal of chemical information and computer sciences. (2002) [Pubmed]
  20. Protein phosphorylation in neutrophils monitored with phosphospecific antibodies. Ohira, T., Zhan, Q., Ge, Q., VanDyke, T., Badwey, J.A. J. Immunol. Methods (2003) [Pubmed]
  21. The C-terminal residues in the alpha-interacting domain (AID) helix anchor CaV beta subunit interaction and modulation of CaV2.3 channels. Berrou, L., Dodier, Y., Raybaud, A., Tousignant, A., Dafi, O., Pelletier, J.N., Parent, L. J. Biol. Chem. (2005) [Pubmed]
  22. Serpin1 of Arabidopsis thaliana is a Suicide Inhibitor for Metacaspase 9. Vercammen, D., Belenghi, B., van de Cotte, B., Beunens, T., Gavigan, J.A., De Rycke, R., Brackenier, A., Inz??, D., Harris, J.L., Van Breusegem, F. J. Mol. Biol. (2006) [Pubmed]
  23. Structural biochemistry of a type 2 RNase H: RNA primer recognition and removal during DNA replication. Chapados, B.R., Chai, Q., Hosfield, D.J., Qiu, J., Shen, B., Tainer, J.A. J. Mol. Biol. (2001) [Pubmed]
  24. Setting the stage for new catalytic functions in designed proteins--exploring the imine pathway in the efficient decarboxylation of oxaloacetate by an Arg-Lys site in a four-helix bundle protein scaffold. Allert, M., Baltzer, L. Chemistry (Weinheim an der Bergstrasse, Germany) (2002) [Pubmed]
  25. Inhibitors of proprotein convertases. Basak, A. J. Mol. Med. (2005) [Pubmed]
  26. Identification of betacellulin as a major peptide growth factor in milk: purification, characterization and molecular cloning of bovine betacellulin. Dunbar, A.J., Priebe, I.K., Belford, D.A., Goddard, C. Biochem. J. (1999) [Pubmed]
  27. Human lung microsomal cytochrome P4501A1 (CYP1A1) activities: impact of smoking status and CYP1A1, aryl hydrocarbon receptor, and glutathione S-transferase M1 genetic polymorphisms. Smith, G.B., Harper, P.A., Wong, J.M., Lam, M.S., Reid, K.R., Petsikas, D., Massey, T.E. Cancer Epidemiol. Biomarkers Prev. (2001) [Pubmed]
  28. Structural properties and mechanisms that govern association of C kinase adapter 1 with protein kinase C3 and the cell periphery. Zhang, L., Wu, S.L., Rubin, C.S. J. Biol. Chem. (2001) [Pubmed]
  29. Relation of streptococcal M protein with human and rabbit tropomyosin: the complete amino acid sequence of human cardiac alpha tropomyosin, a highly conserved contractile protein. Mische, S.M., Manjula, B.N., Fischetti, V.A. Biochem. Biophys. Res. Commun. (1987) [Pubmed]
  30. Identification of a cathepsin G-like proteinase in the MCTC type of human mast cell. Schechter, N.M., Irani, A.M., Sprows, J.L., Abernethy, J., Wintroub, B., Schwartz, L.B. J. Immunol. (1990) [Pubmed]
  31. An active FK506-binding domain of 17,000 daltons is isolated following limited proteolysis of chicken thymus hsp56. Yem, A.W., Reardon, I.M., Leone, J.W., Heinrikson, R.L., Deibel, M.R. Biochemistry (1993) [Pubmed]
  32. Nonkallikrein arginine endopeptidase in the human submaxillary gland: purification and characterization of the enzyme. Watanabe, Y., Suzuki, M., Fujimoto, Y. Biochem. Med. Metab. Biol. (1994) [Pubmed]
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