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Chemical Compound Review

Phe-Trp     (2R)-2-[[(2R)-2-amino-3- phenyl...

Synonyms: AG-B-61279, SureCN11853752, AC1MIC1Z, CTK7D0935, LS-158160, ...
 
 
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Disease relevance of Phe-Trp

  • Previously we reported that the N-terminal Tyr residue of nsP4 of Sindbis virus, the type species of the genus Alphavirus, can be substituted with Phe, Trp, or His without altering the wild-type phenotype in cultured cells but that other substitutions tested, except for Met, were lethal or quasilethal [1].
  • Ultraviolet resonance Raman (UVRR) spectra of H2O and D2O solutions of the nucleoside (dA, dG, dC, dT) and aromatic amino acid (Phe, Trp, Tyr) constituents of DNA viruses have been obtained with laser excitation wavelengths of 257, 244, 238, and 229 nm [2].
  • All the typical metalloendopeptidases tested, such as thermolysin, Pseudomonas aeruginosa (Ps.) elastase, Streptomyces griseus metalloendopeptidases I and II (SGMPI and SGMPII), and alkinonase A, a metalloendopeptidase from Streptomyces violaceorectus, cleaved this substrate strictly at a Phe-Trp bond, leading to a marked increase in fluorescence [3].
 

High impact information on Phe-Trp

  • The optimal P4 to P2 substrate specificity for plasmin was P4-Lys/Nle (norleucine)/Val/Ile/Phe, P3-Xaa, and P2-Tyr/Phe/Trp [4].
  • Novel cationic antimicrobial peptides typified by structures such as KKKKKKAAXAAWAAXAA-NH2, where X = Phe/Trp, and several of their analogues display high activity against a variety of bacteria but exhibit no hemolytic activity even at high dose levels in mammalian erythrocytes [5].
  • In EP2, the ability to stimulate cAMP formation was lost by mutation of Tyr(143) into Ala but retained by mutations into Phe, Trp, and Leu [6].
  • Exchanging the amino acid of Phe, Trp, or Tyr in this newly identified signature motif cluster may influence these peptides to interact with AR [7].
  • MCT8 did not transport Leu, Phe, Trp, or Tyr [8].
 

Biological context of Phe-Trp

 

Associations of Phe-Trp with other chemical compounds

  • The heat capacity change for transfer from water into octanol was -45, -73, -81, and -88 cal/mol K for Ala, Phe, Trp, and Pro peptides, respectively [12].
  • For Phe, Trp, Asn, His, and Ser, the isoelectric point (IEP) of TiO2 shifted to a lower pH with increasing decomposition rates upon adsorption on TiO2, suggesting that the effective adsorption and photocatalytic sites for these amino acids should be the basic terminal OH on the solid surface [13].
 

Gene context of Phe-Trp

  • A few EH domains, such as the third EH domain (EH(3)) of human Eps15, prefer to bind Phe-Trp (FW) sequences [11].
  • The in vitro "immune response" to the hapten NIP was dominated by the 9-1 segment (VH3 family), and that to phOx by the VH26 segment (VH3 family) with an invariant aromatic residue (Tyr, Phe, Trp) at residue 97 of CDR3 [14].
  • The antigen binding fragment analogs labeled with 15N of the main chain amide group of the aromatic residues (His, Phe, Trp, and Tyr) were used [15].
  • Circular dichroism measurements show that the secondary/tertiary structure organization of each subunit is unaffected by the SDS concentration, while the mutation Phe/Trp causes weakening in quaternary structure [16].
  • In contrast to P1 Leu, Met, Phe, Trp, and Tyr appearing in other chymotrypsin inhibitors, a P1 Asn in the novel inhibitor may cause a weak binding (Ki = 3.52 microM) with chymotrypsin [17].

References

  1. Suppressor mutations that allow sindbis virus RNA polymerase to function with nonaromatic amino acids at the N-terminus: evidence for interaction between nsP1 and nsP4 in minus-strand RNA synthesis. Shirako, Y., Strauss, E.G., Strauss, J.H. Virology (2000) [Pubmed]
  2. UV resonance Raman spectroscopy of DNA and protein constituents of viruses: assignments and cross sections for excitations at 257, 244, 238, and 229 nm. Wen, Z.Q., Thomas, G.J. Biopolymers (1998) [Pubmed]
  3. Application of bimane-peptide substrates to spectrofluorometric assays of metalloendopeptidases. Kajiwara, K., Kumazaki, T., Sato, E., Kanaoka, Y., Ishii, S. J. Biochem. (1991) [Pubmed]
  4. Synthesis of positional-scanning libraries of fluorogenic peptide substrates to define the extended substrate specificity of plasmin and thrombin. Backes, B.J., Harris, J.L., Leonetti, F., Craik, C.S., Ellman, J.A. Nat. Biotechnol. (2000) [Pubmed]
  5. Basis for selectivity of cationic antimicrobial peptides for bacterial versus mammalian membranes. Glukhov, E., Stark, M., Burrows, L.L., Deber, C.M. J. Biol. Chem. (2005) [Pubmed]
  6. A cluster of aromatic amino acids in the i2 loop plays a key role for Gs coupling in prostaglandin EP2 and EP3 receptors. Sugimoto, Y., Nakato, T., Kita, A., Takahashi, Y., Hatae, N., Tabata, H., Tanaka, S., Ichikawa, A. J. Biol. Chem. (2004) [Pubmed]
  7. The use of phage display technique for the isolation of androgen receptor interacting peptides with (F/W)XXL(F/W) and FXXLY new signature motifs. Hsu, C.L., Chen, Y.L., Yeh, S., Ting, H.J., Hu, Y.C., Lin, H., Wang, X., Chang, C. J. Biol. Chem. (2003) [Pubmed]
  8. Identification of monocarboxylate transporter 8 as a specific thyroid hormone transporter. Friesema, E.C., Ganguly, S., Abdalla, A., Manning Fox, J.E., Halestrap, A.P., Visser, T.J. J. Biol. Chem. (2003) [Pubmed]
  9. Differential role of the carboxyl-terminal tyrosine in down-regulation and sequestration of the m2 muscarinic acetylcholine receptor. Goldman, P.S., Nathanson, N.M. J. Biol. Chem. (1994) [Pubmed]
  10. Substitution of Cys-560 by Phe, Trp, Tyr, and Ser in the first zinc finger of human androgen receptor affects hormonal sensitivity and transcriptional activation. Warriar, N., Yu, C., Pagé, N., Govindan, M.V. J. Biol. Chem. (1994) [Pubmed]
  11. Solution structure of Eps15's third EH domain reveals coincident Phe-Trp and Asn-Pro-Phe binding sites. Enmon, J.L., de Beer, T., Overduin, M. Biochemistry (2000) [Pubmed]
  12. Amino acid side-chain contributions to free energy of transfer of tripeptides from water to octanol. Kim, A., Szoka, F.C. Pharm. Res. (1992) [Pubmed]
  13. Adsorption and Photocatalytic Decomposition of Amino Acids in TiO(2) Photocatalytic Systems. Tran, T.H., Nosaka, A.Y., Nosaka, Y. The journal of physical chemistry. B, Condensed matter, materials, surfaces, interfaces & biophysical (2006) [Pubmed]
  14. By-passing immunisation. Human antibodies from synthetic repertoires of germline VH gene segments rearranged in vitro. Hoogenboom, H.R., Winter, G. J. Mol. Biol. (1992) [Pubmed]
  15. Role of the domain-domain interaction in the construction of the antigen combining site. A comparative study by 1H-15N shift correlation NMR spectroscopy of the Fv and Fab fragments of anti-dansyl mouse monoclonal antibody. Takahashi, H., Tamura, H., Shimba, N., Shimada, I., Arata, Y. J. Mol. Biol. (1994) [Pubmed]
  16. Functional properties of subunit interactions in human cytidine deaminase. Vincenzetti, S., De Sanctis, G., Costanzi, S., Cristalli, G., Mariani, P., Mei, G., Neuhard, J., Natalini, P., Polzonetti, V., Vita, A. Protein Eng. (2003) [Pubmed]
  17. Purification and characterization of a chymotrypsin inhibitor from the venom of Ophiophagus hannah (King Cobra). Chang , L., Chung, C., Huang, H.B., Lin, S. Biochem. Biophys. Res. Commun. (2001) [Pubmed]
 
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