Intein-mediated cyclization of randomized peptides in the periplasm of Escherichia coli and their extracellular secretion

ACS Chemical Biology

Volumn 5, Issue 7, 2010, Pages 691-700

  Deschuyteneer, Geneviève ^a   Garcia, Stéphanie ^a   Michiels, Benjamin ^a   Baudoux, Bruno ^a   Degand, Hervé ^a   Morsomme, Pierre ^a   Soumillion, Patrice ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAMASE TEM 1; CYSTEINE; GLYCINE; INTEIN; OUTER MEMBRANE PROTEIN; PEPTIDE; SERINE; SIGNAL PEPTIDE;

AMINO ACID SEQUENCE; ARTICLE; BACTERIAL STRAIN; BACTERIOPHAGE; CYCLIZATION; CYTOPLASM; ESCHERICHIA COLI; MICROORGANISM; MUTANT; NONHUMAN; OUTER MEMBRANE; PATHOGENESIS; PRIORITY JOURNAL; PROTEIN SECRETION; SYNECHOCYSTIS;

BASE SEQUENCE; BETA-LACTAMASES; CYCLIZATION; CYSTEINE; ESCHERICHIA COLI; INTEINS; PEPTIDE LIBRARY; PEPTIDES, CYCLIC; PERIPLASM; PROTEIN ENGINEERING; PROTEIN FOLDING; PROTEIN SPLICING;

ESCHERICHIA COLI; SYNECHOCYSTIS SP.;

EID: 77955030266     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/cb100072u     Document Type: Article

References (33)

1. Falciani, C., Lozzi, L., Aless, Pini, R., and Bracci, L (2005) Bioactive peptides from libraries, Chem. Biol. 12, 417-426.
2. Boldt, G. E., Dickerson, T. J., and Janda, K. D. (2006) Emerging chemical and biological approaches forthe preparation of discovery libraries, Drug Discovery Today 11,143-148.
3. Mersich, C., and Jungbauer, A. (2008) Generation of bioactive peptides by biological libraries, J. Chromatogr., B 861,160-170.
4. Cane, D. E., Walsh, C. T., and Khosla, C. (1998) Harnessing the biosynthetic code: combinations, permutations, and mutations, Science 282, 63-68.
5. Boer, A. L D., and Schmidt-Dannert, C. (2003) Recent efforts in engineering microbial cells to produce new chemical compounds, Curr. Opin. Chem. Biol. 7, 273-278.
6. Du, L., and Shen, B. (2001) Biosynthesis of hybrid peptidepolyketide natural products, Curr. Opin. Drug Discovery Dev. 4, 215-228.
7. Scott, C. P., Abel-Santos, E., Jones, A. D., and Benkovic, S. J. (2001) Structural requirements forthe biosynthesis of backbone cyclic peptide libraries, Chem. Biol. 8, 801-815.
8. Scott, C. P., Abel-Santos, E., Wall, M., Wahnon, D. C., and Benkovic, S.J. (1999) Production of cyclic peptides and proteins in vivo, Proc. Natl. Acad. Sci. U.S.A. 96,13638-13643.
9. Evans, T. C., Benner, J., and Xu, M. (1999) The cyclization and polymerization of bacterially expressed proteins using modified self-splicing inteins, J. Biol. Chem. 274,18359-18363.
10. Tavassoli, A., and Benkovic, S.J. (2007) Split-intein mediated circular ligation used in the synthesis of cyclic peptide libraries in E. coli, Nat. Protoc. 2,1126-1133.
11. Horswill, A. R., and Benkovic, S.J. (2005) Cyclic peptides, a chemical genetics tool for biologists, Cell Cycle 4, 552-555.
12. Horswill, A. R., and Benkovic, S.J. (2006) Identifying small-molecule modulators of protein-protein interactions, Curr. Protoc. Protein Sci. Unit 19.15.
13. Tavassoli, A., and Benkovic, S.J. (2005) Genetically selected cyclicpeptide inhibitors of AICAR transformylase homodimerization, Angew. Chem., Int. Ed. 44, 2760-2763.
14. Tavassoli, A., Lu, Q., Gam, J., Pan, H., Benkovic, S. J., and Cohen, S. N. (2008) Inhibition of HIV budding by a genetically selected cyclic peptide targeting the Gag-TSG101 interaction, ACS Chem. Biol. 3, 757-764.
15. Cheng, L., Naumann, T. A., Horswill, A. R., Hong, S., Venters, B. J., Tomsho, J. W., Benkovic, S. J., and Keiler, K. C. (2007) Discovery of antibacterial cyclic peptides that inhibit the ClpXP protease, Protein Sci. 16, 1535-1542.
16. Naumann, T. A., Tavassoli, A., and Benkovic, S.J. (2008) Genetic selection of cyclic peptide Dam methyltransferase inhibitors, ChemBioChem 9, 194-197.
17. Kinsella, T. M., Ohashi, C. T., Harder, A. G., Yam, G. C., Li, W., Peelle, B., Pali, E. S., Bennett, M. K., Molineaux, S. M., Anderson, D. A., Masuda, E. S., and Payan, D. G. (2002) Retrovirally delivered random cyclic peptide libraries yield inhibitors of interleukin-4 signaling in human B cells, J. Biol. Chem. 277, 37512-37518.
18. Williams, N. K., Prosselkov, P., Liepinsh, E., Line, I., Sharipo, A., Littler, D. R., Curmi, P. M. G., Otting, G., and Dixon, N. E. (2002) In vivo protein cyclization promoted by a circularly permuted Synechocystis sp. PCC6803 DnaB mini-intein, J. Biol. Chem. 277, 7790-7798.
19. Iwai, H., and Plückthun, A. (1999) Circular β-lactamase: stability enhancement by cyclizing the backbone, FEBS Lett. 459,166-172.
20. Wu, H., Xu, M., and Liu, X. (1998) Protein trans-splicing and functional mini-inteins of a cyanobacterial dnaB intein, Biochim. Biophys. Acta 1387, 422-432.
21. Gogarten, J. P., Senejani, A. G., Zhaxybayeva, O., Olendzenski, L., and Hilario, E. (2002) Inteins: structure, function, and evolution, Annu. Rev. Microbiol. 56, 263-287.
22. Mathys, S., Evans, T. C., Chute, I. C., Wu, H., Chong, S., Benner, J., Liu, X. Q., and Xu, M. Q. (1999) Characterization of a self-splicing mini-intein and its conversion into autocatalytic N- and C-terminal cleavage elements: facile production of protein building blocks for protein ligation, Gene 231,1-13.
23. Ludwig, C., Schwarzer, D., and Mootz, H. D. (2008) Interaction studies and alanine scanning analysis of a semi-synthetic split intein reveal thiazoline ring formation from an intermediate of the protein splicing reaction, J. Biol. Chem. 283, 25264-25272.
24. Koshland, D., and Botstein, D. (1982) Evidence for posttranslational translocation of beta-lactamase across the bacterial inner membrane, Cell 30, 893-902.
25. Powers, T., and Walter, P. (1997) Co-translational protein targeting catalyzed by the Escherichia coli signal recognition particle and its receptor, EMBO J. 16,4880-4886.
26. Schierle, C. F., Berkmen, M., Huber, D., Kumamoto, C., Boyd, D., and Beckwith, J. (2003) The DsbA signal sequence directs efficient, cotranslational export of passenger proteins to the Escherichia coli periplasm via the signal recognition particle pathway, J. Bacteriol. 185, 5706-5713.
27. Luirink, J., and Sinning, I. (2004) SRP-mediated protein targeting: structure and function revisited, Biochim. Biophys. Acta 1694,17-35.
28. Nakae, T., and Nikaido, H. (1975) Outer membrane as a diffusion barrier in Salmonella typhimurium. Penetration of oligo- and polysaccharides into isolated outer membrane vesicles and cells with degraded peptidoglycan layer, J. Biol. Chem. 250, 7359-7365.
29. Decad, G. M., and Nikaido, H. (1976) Outer membrane of Gramnegative bacteria. XII. Molecular-sieving function of cell wall, J. Bacteriol. 128, 325-336.
30. Marciano, D. K., Russel, M., and Simon, S. M. (1999) An aqueous channel for filamentous phage export, Science 284,1516-1519.
31. Lee, S. K., and Keasling, J. D. (2005) A propionate-inducible expression system forenteric bacteria, Appl. Environ. Microbiol. 71,6856-6862.
32. Soumillion, P., and Fastrez, J. (1992) A large decrease in heat-shockinduced proteolysis after tryptophan starvation leads to increased expression of phage lambda lysozyme cloned in Escherichia coli, Biochem. J. 286, (Pt 1), 187-191.
33. Patrick, W. M., Firth, A. E., and Blackburn, J. M. (2003) User-friendly algorithms for estimating completeness and diversity in randomized protein-encoding libraries, Protein Eng. 16,451-457.