Adenylation Enzyme Characterization Using γ -18O4-ATP Pyrophosphate Exchange

Chemistry and Biology

Volumn 16, Issue 5, 2009, Pages 473-478

  Phelan, Vanessa V ^a   Du, Yu ^a   McLean, John A ^a   Bachmann, Brian O ^a  

^a VANDERBILT UNIVERSITY   (United States)

Author keywords

CHEMBIO

Indexed keywords

3 HYDROXY 4 METHYLANTHRANILIC ACID; 4-METHYL-3-HYDROXYANTHRANILIC ACID; ADENOSINE TRIPHOSPHATE; AMINO ACID TRANSFER RNA LIGASE; ANTHRAMYCIN; ANTHRANILIC ACID DERIVATIVE; NON RIBOSOMAL PEPTIDE SYNTHASE; NON-RIBOSOMAL PEPTIDE SYNTHASE; OXYGEN; PEPTIDE SYNTHASE; PYROPHOSPHATE;

ARTICLE; BIOCATALYSIS; BIOSYNTHESIS; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KINETICS; MASS SPECTROMETRY; METABOLISM; MULTIGENE FAMILY; SYNTHESIS;

ADENOSINE TRIPHOSPHATE; AMINO ACYL-TRNA SYNTHETASES; ANTHRAMYCIN; ANTHRANILIC ACIDS; BIOCATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIPHOSPHATES; KINETICS; MULTIGENE FAMILY; OXYGEN RADIOISOTOPES; PEPTIDE SYNTHASES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 65749110688     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2009.04.007     Document Type: Article

References (30)

1. Challis G.L., Ravel J., and Townsend C.A. Predictive, structure-based model of amino acid recognition by nonribosomal peptide synthetase adenylation domains. Chem. Biol. 7 (2000) 211-224
2. Cohn M., and Hu A. Isotopic (18O) shift in 31P nuclear magnetic resonance applied to a study of enzyme-catalyzed phosphate-phosphate exchange and phosphate (oxygen)-water exchange reactions. Proc. Natl. Acad. Sci. USA 75 (1978) 200-203
3. Cole F.X., and Schimmel P.R. On the rate law and mechanism of the adenosine triphosphate-pyrophosphate isotope exchange reaction of amino acyl transfer ribonucleic acid synthetases. Biochemistry 9 (1970) 480-489
4. Cornett D.S., Reyzer M.L., Chaurand P., and Caprioli R.M. MALDI imaging mass spectrometry: molecular snapshots of biochemical systems. Nat. Methods 4 (2007) 828-833
5. Dorrestein P.C., Bumpus S.B., Calderone C.T., Garneau-Tsodikova S., Aron Z.D., Straight P.D., Kolter R., Walsh C.T., and Kelleher N.L. Facile detection of acyl and peptidyl intermediates on thiotemplate carrier domains via phosphopantetheinyl elimination reactions during tandem mass spectrometry. Biochemistry 45 (2006) 12756-12766
6. Du L., and Shen B. Identification and characterization of a type II peptidyl carrier protein from the bleomycin producer Streptomyces verticillus ATCC 15003. Chem. Biol. 6 (1999) 507-517
7. Eigner E.A., and Loftfield R.B. Kinetic techniques for the investigation of amino acid: tRNA ligases (aminoacyl-tRNA synthetases, amino acid activating enzymes). Methods Enzymol. 29 (1974) 601-619
8. Fischbach M.A., and Walsh C.T. Assembly-line enzymology for polyketide and nonribosomal peptide antibiotics: Logic, machinery, and mechanisms. Chem. Rev. 106 (2006) 3468-3496
9. Fischbach M.A., Lai J.R., Roche E.D., Walsh C.T., and Liu D.R. Directed evolution can rapidly improve the activity of chimeric assembly-line enzymes. Proc. Natl. Acad. Sci. USA 104 (2007) 11951-11956
10. Francklyn C.S., First E.A., Perona J.J., and Hou Y.M. Methods for kinetic and thermodynamic analysis of aminoacyl-tRNA synthetases. Methods 44 (2008) 100-118
11. Hicks L.M., O'Connor S.E., Mazur M.T., Walsh C.T., and Kelleher N.L. Mass spectrometric interrogation of thioester-bound intermediates in the initial stages of epothilone biosynthesis. Chem. Biol. 11 (2004) 327-335
12. Hoard D.E., and Ott D.G. Conversion of mono- and oligodeoxyribonucleotides to 5-triphosphates. J. Am. Chem. Soc. 87 (1965) 1785-1788
13. Hu Y., Phelan V., Ntai I., Farnet C.M., Zazopoulos E., and Bachmann B.O. Benzodiazepine biosynthesis in Streptomyces refuineus. Chem. Biol. 14 (2007) 691-701
14. Joseph D.R., and Muench K.H. Tryptophanyl transfer ribonucleic acid synthetase of Escherichia coli. I. Purification of the enzyme and of tryptrophan transfer ribonucleic acid. J. Biol. Chem. 246 (1971) 7602-7609
15. La Clair J.J., Foley T.L., Schegg T.R., Regan C.M., and Burkart M.D. Manipulation of carrier proteins in antibiotic biosynthesis. Chem. Biol. 11 (2004) 195-201
16. Lee S.G., and Lipmann F. Tyrocidine synthetase system. Methods Enzymol. 43 (1975) 585-602
17. Linne U., and Marahiel M.A. Reactions catalyzed by mature and recombinant nonribosomal peptide synthetases. Protein Eng. 388 (2004) 293-315
18. Linne U., and Marahiel M.A. Reactions catalyzed by mature and recombinant nonribosomal peptide synthetases. Methods Enzymol. 388 (2004) 293-315
19. McLean J.A., Ridenour W.B., and Caprioli R.M. Profiling and imaging of tissues by imaging ion mobility-mass spectrometry. J. Mass Spectrom. 42 (2007) 1099-1105
20. Neres J., Wilson D.J., Celia L., Beck B.J., and Aldrich C.C. Aryl acid adenylating enzymes involved in siderophore biosynthesis: fluorescence polarization assay, ligand specificity, and discovery of non-nucleoside inhibitors via high-throughput screening. Biochemistry 47 (2008) 11735-11749
21. Otten L.G., Schaffer M.L., Villiers B.R., Stachelhaus T., and Hollfelder F. An optimized ATP/PP(i)-exchange assay in 96-well format for screening of adenylation domains for applications in combinatorial biosynthesis. Biotechnol. J. 2 (2007) 232-240
22. Pfeifer E., Pavela-Vrancic M., von Dohren H., and Kleinkauf H. Characterization of tyrocidine synthetase 1 (TY1): requirement of posttranslational modification for peptide biosynthesis. Biochemistry 34 (1995) 7450-7459
23. Pfennig F., Schauwecker F., and Keller U. Molecular characterization of the genes of actinomycin synthetase I and of a 4-methyl-3-hydroxyanthranilic acid carrier protein involved in the assembly of the acylpeptide chain of actinomycin in Streptomyces. J. Biol. Chem. 274 (1999) 12508-12516
24. Rausch C., Weber T., Kohlbacher O., Wohlleben W., and Huson D.H. Specificity prediction of adenylation domains in nonribosomal peptide synthetases (NRPS) using transductive support vector machines (TSVMs). Nucleic Acids Res. 33 (2005) 5799-5808
25. Sieber S.A., and Marahiel M.A. Molecular mechanisms underlying nonribosomal peptide synthesis: Approaches to new antibiotics. Chem. Rev. 105 (2005) 715-738
26. Stachelhaus T., Mootz H.D., and Marahiel M.A. The specificity-conferring code of adenylation domains in nonribosomal peptide synthetases. Chem. Biol. 6 (1999) 493-505
27. Stern R., DeLuca M., Mehler A.H., and McElroy W.D. Role of sulfhydryl groups in activating enzymes. Properties of Escherichia coli lysine-transfer ribonucleic acid synthetase. Biochemistry 5 (1966) 126-130
28. Sun G., Yang K., Zhao Z.D., Guan S.P., Han X.L., and Gross R.W. Shotgun metabolomics approach for the analysis of negatively charged water-soluble cellular metabolites from mouse heart tissue. Anal. Chem. 79 (2007) 6629-6640
29. Xing J., Apedo A., Tymiak A., and Zhao N. Liquid chromatographic analysis of nucleosides and their mono-, di- and triphosphates using porous graphitic carbon stationary phase coupled with electrospray mass spectrometry. Rapid Commun. Mass Spectrom. 18 (2004) 1599-1606
30. Zou Y., and Yin J. Alkyne-functionalized chemical probes for assaying the substrate specificities of the adenylation domains in nonribosomal peptide synthetases. Chem. Bio. Chem. 9 (2008) 2804-2810