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Chemical Compound Review

pentaglycine     2-[2-[2-[2-(2- aminoethanoylamino) ethanoyla...

Synonyms: CHEMBL14390, AG-G-77396, G5755_SIGMA, NSC-96353, CHEBI:114248, ...
 
 
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Disease relevance of pentaglycine

 

High impact information on pentaglycine

 

Chemical compound and disease context of pentaglycine

 

Biological context of pentaglycine

 

Anatomical context of pentaglycine

 

Associations of pentaglycine with other chemical compounds

 

Gene context of pentaglycine

  • To explore Arg(19) and the midregion (residues 10-15), we designed the novel PTH scaffold peptide, PG5, which has the PTH(1-9) domain linked to the PTH(15-31) segment via a pentaglycine spacer [16].
  • Lysostaphin is an endopeptidase that cleaves the pentaglycine cross-bridges of the staphylococcal cell wall rapidly lysing the bacteria [17].
  • Sortase B of S. aureus recognizes a motif NPQTN, cleaves the polypeptide after the Thr residue, and attaches the protein to pentaglycine cross-bridges [18].
  • The apparent activation energy of hydrolysis of pentaglycine bridges in Staphylococcus peptidoglycan is 77.9 kJ/mol [19].

References

  1. Dynamic structure of whole cells probed by nuclear Overhauser enhanced nitrogen-15 nuclear magnetic resonance spectroscopy. Lapidot, A., Irving, C.S. Proc. Natl. Acad. Sci. U.S.A. (1977) [Pubmed]
  2. Antibodies to staphylococcal peptidoglycan and its peptide epitopes, teichoic acid, and lipoteichoic acid in sera from blood donors and patients with staphylococcal infections. Wergeland, H.I., Haaheim, L.R., Natås, O.B., Wesenberg, F., Oeding, P. J. Clin. Microbiol. (1989) [Pubmed]
  3. The essential Staphylococcus aureus gene fmhB is involved in the first step of peptidoglycan pentaglycine interpeptide formation. Rohrer, S., Ehlert, K., Tschierske, M., Labischinski, H., Berger-Bächi, B. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  4. Cell wall-targeting domain of glycylglycine endopeptidase distinguishes among peptidoglycan cross-bridges. Lu, J.Z., Fujiwara, T., Komatsuzawa, H., Sugai, M., Sakon, J. J. Biol. Chem. (2006) [Pubmed]
  5. In vitro assembly of a complete, pentaglycine interpeptide bridge containing cell wall precursor (lipid II-Gly5) of Staphylococcus aureus. Schneider, T., Senn, M.M., Berger-Bächi, B., Tossi, A., Sahl, H.G., Wiedemann, I. Mol. Microbiol. (2004) [Pubmed]
  6. Identification of Staphylococcus aureus virulence genes in a murine model of bacteraemia using signature-tagged mutagenesis. Mei, J.M., Nourbakhsh, F., Ford, C.W., Holden, D.W. Mol. Microbiol. (1997) [Pubmed]
  7. Selection of chymotrypsin inhibitors from a conformationally-constrained combinatorial peptide library. McBride, J.D., Freeman, N., Domingo, G.J., Leatherbarrow, R.J. J. Mol. Biol. (1996) [Pubmed]
  8. Nitrogen-15 and carbon-13 dynamic nuclear magnetic resonance study of chain segmental motion of the peptidoglycan pentaglycine chain of 15N-Gly- and 13C2-Gly-labeled Staphylococcus aureus cells and isolated cell walls. Lapidot, A., Irving, C.S. Biochemistry (1979) [Pubmed]
  9. Cell wall monoglycine cross-bridges and methicillin hypersusceptibility in a femAB null mutant of methicillin-resistant Staphylococcus aureus. Strandén, A.M., Ehlert, K., Labischinski, H., Berger-Bächi, B. J. Bacteriol. (1997) [Pubmed]
  10. Hydrolysis of glycine-containing elastin pentapeptides by LasA, a metalloelastase from Pseudomonas aeruginosa. Vessillier, S., Delolme, F., Bernillon, J., Saulnier, J., Wallach, J. Eur. J. Biochem. (2001) [Pubmed]
  11. Specific effects of synthetic oligopeptides on cultured animal cells. Franek, F., Katinger, H. Biotechnol. Prog. (2002) [Pubmed]
  12. Studies on the immunochemistry of Staphylococcus aureus cell wall: antigenicity of pentaglycine bridges. Ranu, R.S. Med. Microbiol. Immunol. (Berl.) (1975) [Pubmed]
  13. Induction of release of tumor necrosis factor from human monocytes by staphylococci and staphylococcal peptidoglycans. Timmerman, C.P., Mattsson, E., Martinez-Martinez, L., De Graaf, L., Van Strijp, J.A., Verbrugh, H.A., Verhoef, J., Fleer, A. Infect. Immun. (1993) [Pubmed]
  14. Lysostaphin cream eradicates Staphylococcus aureus nasal colonization in a cotton rat model. Kokai-Kun, J.F., Walsh, S.M., Chanturiya, T., Mond, J.J. Antimicrob. Agents Chemother. (2003) [Pubmed]
  15. Rotating ring-disk electrode study of copper(II) complexes of the model peptides triglycine, tetraglycine, and pentaglycine. Woltman, S.J., Alward, M.R., Weber, S.G. Anal. Chem. (1995) [Pubmed]
  16. Cooperative interaction of arginine-19 and the N-terminal signaling domain in the affinity and potency of parathyroid hormone. Tsomaia, N., Shimizu, M., Shimizu, N., Gardella, T.J., Mierke, D.F. Biochemistry (2004) [Pubmed]
  17. Comparison of four methods for determining lysostaphin susceptibility of various strains of Staphylococcus aureus. Kusuma, C.M., Kokai-Kun, J.F. Antimicrob. Agents Chemother. (2005) [Pubmed]
  18. Structures of sortase B from Staphylococcus aureus and Bacillus anthracis reveal catalytic amino acid triad in the active site. Zhang, R., Wu, R., Joachimiak, G., Mazmanian, S.K., Missiakas, D.M., Gornicki, P., Schneewind, O., Joachimiak, A. Structure (2004) [Pubmed]
  19. Michaelis-menten kinetics for determining enzymatic activity of lysostaphin. Surovtsev, V.I., Fedorov, T.V., Borozdina, M.A. Biochemistry Mosc. (2004) [Pubmed]
 
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