New chromogenic dipeptide substrate for continuous assay of the D-alanyl-D-alanine dipeptidase VanX required for high-level vancomycin resistance

Journal of Peptide Research

Volumn 62, Issue 2, 2003, Pages 88-95

  Anissimova, M ^a   Yaouancq, L ^a   Badet Denisot, M A ^a   Badet, Bernard ^a  

^a CNRS   (France)

Author keywords

alkylthioglycine substrate; Continuous assay; Ellman's reagent; VanX dipeptidase

Indexed keywords

5,5' DITHIOBIS(2 NITROBENZOIC ACID); ALANINE DERIVATIVE; DEXTRO ALANINE ALPHA 4 DIFLUOROMETHYLPHENYLTHIOGLYCINE HYDROXIDE; DEXTRO ALANINE ALPHA PHENYLTHIOGLYCINE DEXTRO ALANINE DEXTRO GLYCINE(S PHENYL)HYDROXIDE; DEXTRO ALANINE DEXTRO ALANINE; DEXTRO ALANINE DEXTRO ALANINE AMINOPEPTIDASE; DIPEPTIDE DERIVATIVE; ENZYME INHIBITOR; GLYCINE DERIVATIVE; PHENYLTHIOGLYCINE; PROTEIN DERIVATIVE; PROTEIN VANX; THIOPHENOL; UNCLASSIFIED DRUG; VANCOMYCIN;

ARTICLE; DRUG EFFECT; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME INHIBITION; HYDROLYSIS; KINETICS; MICHAELIS CONSTANT; PRIORITY JOURNAL; PROTEIN SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY;

BACTERIAL PROTEINS; CHROMOGENIC COMPOUNDS; DIPEPTIDASES; DIPEPTIDES; ENZYME INHIBITORS; KINETICS; PHENOLS; SERINE-TYPE D-ALA-D-ALA CARBOXYPEPTIDASE; SPECTROPHOTOMETRY, ULTRAVIOLET; SULFHYDRYL COMPOUNDS; VANCOMYCIN; VANCOMYCIN RESISTANCE;

EID: 0038684091     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1034/j.1399-3011.2003.00072.x     Document Type: Article

References (16)

1. Arthur, M., Reynolds, P. & Courvalin, P. (1996) Glycopeptide resistance in Enterococci. Trends Microb. 41, 401-407.
2. Reynolds, P.E., Depardieu, F., Dutka-Malen, S., Arthur, M. & Courvalin, P. (1994) Glycopeptide resistance mediated by Enterococcal transposon Tn1546 requires production of VanX for hydrolysis of D-alanyl-D-alanine. Mol. Microbiol. 13, 1065-1070.
3. Wu, Z., Wright, G.D. & Walsh, C.T. (1995) Overexpression, purification, and characterization of VanX, a D-,D-dipeptidase which is essential for vancomycin resistance in Enterococcus faecium BM4147. Biochemistry 34, 2455-2463.
4. Yang, K.-W., Brandt, J.J., Chatwood, L.L. & Crowder, M.W. (2000) Phosphonamidate and phosphothioate dipeptides as potential inhibitors of VanX. Bioorg. Med. Chem. Lett. 10, 1085-1087.
5. Araoz, R., Anhalt, E., René, L., Badet-Denisot, M.-A., Courvalin, P. & Badet, B. (2000) Mechanism-based inactivation of VanX, a D-alanyl-D-alanine dipeptidase necessary for vancomycin resistance. Biochemistry 39, 15971-15979.
6. McCafferty, D.G., Lessard, I.A. & Walsh, C.T. (1997) Mutational analysis of potential zinc-binding residues in the active site of the Enterococcal D-Ala-D-Ala dipeptidase VanX. Biochemistry 36, 10498-10505.
7. Doi, E., Shibata, D. & Matoba, T. (1981) Modified colorimetric ninhydrin methods for peptidase assay. Anal. Biochem. 118, 173-184.
8. Tu, J. & Chu, Y.H. (1998) Vancomycin resistance in Enterococcus faecium: a capillary electrophoresis-based assay for VanX enzyme. Anal. Biochem. 264, 293-296.
9. Brandt, J.J., Chatwood, L.L. & Crowder, M.W. (1999) Continuous assay for VanX, the D-alanyl-D-alanine dipeptidase required for high-level vancomycin resistance. Anal. Biochem. 272, 94-99.
10. Kingsbury, W.D. & Boehm, J.C. (1986) Synthesis of α-thiophenylglycine peptides. Int. J. Peptide Protein Res. 27, 659-665.
11. Ellman, G.L. (1959) Tissue sulfhydryl groups. Arch. Biochem. Biophys. 82, 70-77.
12. 8. Int. J. Peptide Res. 37, 331-340.
13. Kraus, J.L. & Attardo, G. (1992) Synthesis and biological activities of new N-formylated methionyl peptides containing an -substituted glycine residue. Eur. J. Med. Chem. 27, 19-26.
14. Segel, I.H. (1993) Enzyme Kinetics. Wiley, New York.
15. Guo, X.-C., Rajagopalan, P.T.R. & Pei, D. (1999) A direct spectrometric assay for peptide deformylase. Anal. Biochem. 273, 298-304.
16. Zhou, Y., Guo, X.-C., Yi, T., Yoshimoto, T. & Per, D. (2000) Two continuous spectrophotometric assays for methionine aminopeptidase. Anal. Biochem. 280, 159-165.