Crosslinking Studies of Protein-Protein Interactions in Nonribosomal Peptide Biosynthesis

Chemistry and Biology

Volumn 16, Issue 4, 2009, Pages 372-381

  Hur, Gene H ^a   Meier, Jordan L ^a   Baskin, Jeremy ^b   Codelli, Julian A ^b   Bertozzi, Carolyn R ^b   Marahiel, Mohamed A ^c   Burkart, Michael D ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

CHEMBIO; PROTEINS

Indexed keywords

ALKYNE; AZIDE; BACTERIAL PROTEIN; COPPER; CROSS LINKING REAGENT; DRUG DERIVATIVE; PANTETHEINE; PEPTIDE SYNTHASE;

ARTICLE; CATALYSIS; CHEMISTRY; METABOLISM; METHODOLOGY; NONRIBOSOMAL PEPTIDE SYNTHESIS; PROTEIN ANALYSIS; PROTEIN DOMAIN; SYNTHESIS;

ALKYNES; AZIDES; BACTERIAL PROTEINS; CATALYSIS; COPPER; CROSS-LINKING REAGENTS; PANTETHEINE; PEPTIDE BIOSYNTHESIS, NUCLEIC ACID-INDEPENDENT; PEPTIDE SYNTHASES; PROTEIN INTERACTION DOMAINS AND MOTIFS; PROTEIN INTERACTION MAPPING;

EID: 64749111406     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2009.02.009     Document Type: Article

References (41)

1. Agard N.J., Prescher J.A., and Bertozzi C.R. A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems. J. Am. Chem. Soc. 126 (2004) 15046-15047
2. Alexander J.P., and Cravatt B.F. Mechanism of carbamate inactivation of FAAH: implications for the design of covalent inhibitors and in vivo functional probes for enzymes. Chem. Biol. 12 (2005) 1179-1187
3. Baskin J.M., Prescher J.A., Laughlin S.T., Agard N.J., Chang P.V., Miller I.A., Lo A., Codelli J.A., and Bertozzi C.R. Copper-free click chemistry for dynamic in vivo imaging. Proc. Natl. Acad. Sci. USA 104 (2007) 16793-16797
4. Belshaw P.J., Walsh C.T., and Stachelhaus T. Aminoacyl-CoAs as probes of condensation domain selectivity in nonribosomal peptide synthesis. Science 284 (1999) 486-489
5. I-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective. Eur. J. Org. Chem. 1 (2006) 51-68
6. Broadhurst R.W., Nietlispach D., Wheatcroft M.P., Leadlay P.F., and Weissman K.J. The structure of docking domains in modular polyketide synthases. Chem. Biol. 10 (2003) 723-731
7. Codelli J.A., Baskin J.M., Agard N.J., and Bertozzi C.R. Second-generation difluorinated cyclooctynes for copper-free click chemistry. J. Am. Chem. Soc. 130 (2008) 11486-11493
8. Chiocchini C., Linne U., and Stachelhaus T. In vivo biocombinatorial synthesis of lipopeptides by COM domain-mediated reprogramming of the surfactin biosynthetic complex. Chem. Biol. 13 (2006) 899-908
9. de Ferra F., Rodriguez F., Tortora O., Tosi C., and Grandi G. Engineering of peptide synthetases. Key role of the thioesterase-like domain for efficient production of recombinant peptides. J. Biol. Chem. 272 (1997) 25304-25309
10. Eppelmann K., Stachelhaus T., and Marahiel M.A. Exploitation of the selectivity-conferring code of nonribosomal peptide synthetases for the rational design of novel peptide antibiotics. Biochemistry 41 (2002) 9718-9726
11. Hahn M., and Stachelhaus T. Selective interaction between nonribosomal peptide synthetases is facilitated by short communication-mediating domains. Proc. Natl. Acad. Sci. USA 101 (2004) 15585-15590
12. Hahn M., and Stachelhaus T. Harnessing the potential of communication-mediating domains for the biocombinatorial synthesis of nonribosomal peptides. Proc. Natl. Acad. Sci. USA 103 (2006) 275-280
13. Keating T.A., Marshall C.G., Walsh C.T., and Keating A.E. The structure of VibH represents nonribosomal peptide synthetase condensation domain, cyclization and epimerization domains. Nat. Struct. Biol. 9 (2002) 522-526
14. Krasinski A., Radic Z., Manetsch R., Raushel J., Taylor P., Sharpless K.B., and Kolb H.C. In situ selection of lead compounds by click chemistry: target-guided optimization of acetylcholinesterase inhibitors. J. Am. Chem. Soc. 127 (2005) 6686-6692
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. Laughlin S.T., Baskin J.M., Amacher S.L., and Bertozzi C.R. In vivo imaging of membrane-associated glycans in developing zebrafish. Science 320 (2008) 664-667
17. Lewis W.G., Green L.G., Grynszpan F., Radic Z., Carlier P.R., Taylor P., Finn M.G., and Sharpless K.B. Click chemistry in situ: acetylcholinesterase as a reaction vessel for the selective assembly of a femtomolar inhibitor from an array of building blocks. Angew. Chem. Int. Ed. Engl. 41 (2002) 1053-1057
18. Lundquist IV J.T., and Pelletier J.C. Improved solid-phase peptide synthesis method utilizing alpha-azide-protected amino acids. Org. Lett. 3 (2001) 781-783
19. Marahiel M.A., Stachelhaus T., and Mootz H.D. Modular peptide synthetases involved in nonribosomal peptide synthesis. Chem. Rev. 97 (1997) 2651-2674
20. Mercer A.C., and Burkart M.D. The ubiquitous carrier protein-a window to metabolite biosynthesis. Nat. Prod. Rep. 24 (2007) 750-773
21. Mittenhuber G., Weckermann R., and Marahiel M.A. Gene cluster containing the genes for tyrocidine synthetases 1 and 2 from Bacillus brevis: evidence for an operon. J. Bacteriol. 171 (1989) 4881-4887
22. Mocharla V.P., Colasson B., Lee L.V., Roper S., Sharpless K.B., Wong C.H., and Kolb H.C. In situ click chemistry: enzyme-generated inhibitors of carbonic anhydrase II. Angew. Chem. Int. Ed. Engl. 44 (2004) 116-120
23. Mock W.L., Irra T.A., Wepsiec J.P., and Manimaran T.L. Cycloaddition induced by cucurbituril. A case of pauling principle catalysis. J. Org. Chem. 48 (1983) 3619-3620
24. Mock W.L., Irra T.A., Wepsiec J.P., and Adhya M. Catalysis by cucurbituril. The significance of bound-substrate destabilization for induced triazole formation. J. Org. Chem. 54 (1989) 5302-5308
25. Mootz H.D., and Marahiel M.A. The tyrocidine biosynthesis operon of Bacillus brevis: complete nucleotide sequence and biochemical characterization of functional internal adenylation domains. J. Bacteriol. 179 (1997) 6843-6850
26. Mootz H.D., Kessler N., Linne U., Eppelmann K., Schwarzer D., and Marahiel M.A. Decreasing the ring size of a cyclic nonribosomal peptide antibiotic by in-frame module deletion in the biosynthetic genes. J. Am. Chem. Soc. 124 (2002) 10980-10981
27. Ning X., Guo J., Wolfert M.A., and Boons G.J. Visualizing metabolically labeled glycoconjugates of living cells by copper-free and fast huisgen cycloadditions. Angew. Chem. Int. Ed. Engl. 47 (2008) 2253-2255
28. Quadri L.E., Weinreb P.H., Lei M., Nakano M.M., Zuber P., and Walsh C.T. Characterization of Sfp, a Bacillus subtilis phosphopantetheinyl transferase for peptidyl carrier protein domains in peptide synthetases. Biochemistry 37 (1998) 1585-1595
29. Schneider A., Stachelhaus T., and Marahiel M.A. Targeted alteration of the substrate specificity of peptide synthetases by rational module swapping. Mol. Gen. Genet. 257 (1998) 308-318
30. Shen B., Du L., Sanchez C., Edwards D.J., Chen M., and Murrell J.M. Cloning and characterization of the bleomycin biosynthetic gene cluster from Streptomyces verticillus ATCC15003. J. Nat. Prod. 65 (2002) 422-431
31. Sieber S.A., and Marahiel M.A. Molecular mechanisms underlying nonribosomal peptide synthesis: approaches to new antibiotics. Chem. Rev. 105 (2005) 715-738
32. Sieber S.A., Linne U., Hillson N.J., Roche E., Walsh C.T., and Marahiel M.A. Evidence for a monomeric structure of nonribosomal peptide synthetases. Chem. Biol. 9 (2002) 997-1008
33. Speers A.E., Adam G.C., and Cravatt B.F. Activity-based protein profiling in vivo using a copper(i)-catalyzed azide-alkyne [3+2] cycloaddition. J. Am. Chem. Soc. 125 (2003) 4686-4687
34. Stachelhaus T., Mootz H.D., Bergendahl V., and Marahiel M.A. Peptide bond formation in nonribosomal peptide biosynthesis. Catalytic role of the condensation domain. J. Biol. Chem. 273 (1998) 22773-22781
35. Tanovic A., Samel S.A., Essen L.O., and Marahiel M.A. Crystal structure of the termination module of a nonribosomal peptide synthetase. Science 321 (2008) 659-663
36. Tsuji S.Y., Cane D.E., and Khosla C. Selective protein-protein interactions direct channeling of intermediates between polyketide synthase modules. Biochemistry 40 (2001) 2326-2331
37. Wang Q., Chan T.R., Hilgraf R., Fokin V.V., Sharpless K.B., and Finn M.G. Bioconjugation by copper(I)-catalyzed azide-alkyne [3+2] cycloaddition. J. Am. Chem. Soc. 125 (2003) 3192-3193
38. Weissman K.J., and Muller R. Protein-protein interactions in multienzyme megasynthetases. ChemBioChem 9 (2008) 826-848
39. Whiting M., Muldoon J., Lin Y.C., Silverman S.M., Lindstrom W., Olson A.J., Kolb H.C., Finn M.G., Sharpless K.B., Elder J.H., and Fokin V.V. Inhibitors of HIV-1 protease by using in situ click chemistry. Angew. Chem. Int. Ed. Engl. 45 (2006) 1435-1439
40. Worthington A.S., and Burkart M.D. One-pot chemo-enzymatic synthesis of reporter-modified proteins. Org. Biomol. Chem. 4 (2006) 44-46
41. Worthington A.S., Rivera H., Torpey J.W., Alexander M.D., and Burkart M.D. Mechanism-based protein crosslinking probes to investigate carrier protein-mediated biosynthesis. ACS Chem. Biol. 1 (2006) 687-691