Biological synthesis of circular polypeptides

Journal of Biological Chemistry

Volumn 287, Issue 32, 2012, Pages 27026-27032

  Aboye, Teshome L ^a   Camarero, Julio A ^a  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL PRODUCTION; BIOLOGICAL SYNTHESIS; CYCLIC POLYPEPTIDES; FOLDED PROTEINS; IN-VITRO; IN-VIVO; MOLECULAR LIBRARIES; POLYMER THEORY; PROTEIN ENGINEERING; PROTEIN FOLDING KINETICS; PROTEIN STRUCTURES; RECOMBINANT DNA; SYNTHETIC CHEMISTS; THERMODYNAMIC STABILIZATION;

BIOSYNTHESIS; GENETIC ENGINEERING; LIBRARIES; POLYPEPTIDES; PROTEIN FOLDING;

PROTEINS;

CICULAR POLYPEPTIDE; CYCLOPEPTIDE; CYCLOTIDE; POLYPEPTIDE; TRYPSIN INHIBITOR; UNCLASSIFIED DRUG;

CATALYSIS; CYCLIZATION; ENTROPY; EXPRESSED PROTEIN LIGATION; GENE EXPRESSION SYSTEM; GENETIC CODE; GENETIC CODE REPROGRAMMING; NUCLEAR MAGNETIC RESONANCE; PEPTIDE LIBRARY; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEASE CATALYZED TRANSPEPTIDATION; PROTEIN ENGINEERING; PROTEIN FOLDING; PROTEIN STRUCTURE; RECOMBINANT DNA TECHNOLOGY; RIBOSOME; SHORT SURVEY; THERMODYNAMICS; TRANS SPLICING;

PEPTIDES, CYCLIC; PROTEIN SPLICING; THERMODYNAMICS;

EID: 84864538298     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.R111.305508     Document Type: Short Survey

References (50)

1. Thornton, J. M., and Sibanda, B. L. (1983) Amino- and carboxyl-terminal regions in globular proteins. J. Mol. Biol. 167, 443-460 (Pubitemid 13004690)
2. Clark, R. J., Fischer, H., Dempster, L., Daly, N. L., Rosengren, K. J., Nevin, S. T., Meunier, F. A., Adams, D. J., and Craik, D. J. (2005) Engineering stable peptide toxins by means of backbone cyclization: stabilization of the α-conotoxin MII. Proc. Natl. Acad. Sci. U.S.A. 102, 13767-13772 (Pubitemid 41377653)
3. Clark, R. J., Akcan, M., Kaas, Q., Daly, N. L., and Craik, D. J. (2012) Cyclization of conotoxins to improve their biopharmaceutical properties. Toxicon 59, 446-455
4. Plaxco, K. W., Simons, K. T., Ruczinski, I., and Baker, D. (2000) Topology, stability, sequence, and length: defining the determinants of two-state protein folding kinetics. Biochemistry 39, 11177-11183
5. Craik, D. J. (2006) Chemistry. Seamless proteins tie up their loose ends. Science 311, 1563-1564
6. Daly, N. L., Rosengren, K. J., and Craik, D. J. (2009) Discovery, structure, and biological activities of cyclotides. Adv. Drug Deliv. Rev. 61, 918-930
7. Garcia, A. E., and Camarero, J. A. (2010) Biological activities of natural and engineered cyclotides, a novel molecular scaffold for peptide-based therapeutics. Curr. Mol. Pharmacol. 3, 153-163
8. Contreras, J., Elnagar, A. Y., Hamm-Alvarez, S. F., and Camarero, J. A. (2011) Cellular uptake of cyclotide MCoTI-I follows multiple endocytic pathways. J. Controlled Release 155, 134-143
9. Cascales, L., Henriques, S. T., Kerr, M. C., Huang, Y. H., Sweet, M. J., Daly, N. L., and Craik, D. J. (2011) Identification and characterization of a new family of cell-penetrating peptides. Cyclic cell-penetrating peptides. J. Biol. Chem. 286, 36932-36943
10. Henriques, S. T., and Craik, D. J. (2010) Cyclotides as templates in drug design. Drug Discov. Today 15, 57-64
11. Jagadish, K., and Camarero, J. A. (2010) Cyclotides, a promising molecular scaffold for peptide-based therapeutics. Biopolymers 94, 611-616
12. White, C. J., and Yudin, A. K. (2011) Contemporary strategies for peptide macrocyclization. Nat. Chem. 3, 509-524
13. Sancheti, H., and Camarero, J. A. (2009) "Splicing up" drug discovery. Cell-based expression and screening of genetically encoded libraries of backbone-cyclized polypeptides. Adv. Drug Deliv. Rev. 61, 908-917
14. Suter, B., Kittanakom, S., and Stagljar, I. (2008) Two-hybrid technologies in proteomics research. Curr. Opin Biotechnol. 19, 316-323
15. Kimura, R., and Camarero, J. A. (2005) Expressed protein ligation: a new tool for the biosynthesis of cyclic polypeptides. Protein Pept. Lett. 12, 789-794 (Pubitemid 41634859)
16. 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 (Pubitemid 46908238)
17. Ohta, A., Yamagishi, Y., and Suga, H. (2008) Synthesis of biopolymers using genetic code reprogramming. Curr. Opin. Chem. Biol. 12, 159-167
18. Muir, T. W. (2003) Semisynthesis of proteins by expressed protein ligation. Annu. Rev. Biochem. 72, 249-289
19. Dawson, P. E., and Kent, S. B. (2000) Synthesis of native proteins by chemical ligation. Annu. Rev. Biochem. 69, 923-960
20. Berrade, L., and Camarero, J. A. (2009) Expressed protein ligation: a resourceful tool to study protein structure and function. Cell. Mol. Life Sci. 66, 3909-3922
21. Camarero, J. A., and Muir, T. W. (1999) Biosynthesis of a head-to-tail cyclized protein with improved biological activity. J. Am. Chem. Soc. 121, 5597-5598 (Pubitemid 29292991)
22. Camarero, J. A., Pavel, J., and Muir, T. W. (1998) Angew. Chem. Int. Ed. Engl. 37, 347-349
23. Camarero, J. A., Cotton, G. J., Adeva, A., and Muir, T. W. (1998) Chemical ligation of unprotected peptides directly from a solid support. J. Pept. Res. 51, 303-316 (Pubitemid 28136044)
24. Iwai, H., and Plückthun, A. (1999) Circular β-lactamase: stability enhancement by cyclizing the backbone. FEBS Lett. 459, 166-172 (Pubitemid 29475024)
25. Iwai, H., Lingel, A., and Plückthun, A. (2001) Cyclic green fluorescent protein produced in vivo using an artificially split PI-PfuI intein from Pyrococcus furiosus. J. Biol. Chem. 276, 16548-16554
26. Camarero, J. A., Fushman, D., Cowburn, D., and Muir, T. W. (2001) Peptide chemical ligation inside living cells: in vivo generation of a circular protein domain. Bioorg. Med. Chem. 9, 2479-2484 (Pubitemid 32834634)
27. Kimura, R. H., Tran, A. T., and Camarero, J. A. (2006) Biosynthesis of the cyclotide kalata B1 by using protein splicing. Angew. Chem. Int. Ed. Engl. 45, 973-976 (Pubitemid 43198489)
28. Camarero, J. A., Kimura, R. H., Woo, Y. H., Shekhtman, A., and Cantor, J. (2007) Biosynthesis of a fully functional cyclotide inside living bacterial cells. ChemBioChem 8, 1363-1366 (Pubitemid 47300326)
29. Austin, J., Wang, W., Puttamadappa, S., Shekhtman, A., and Camarero, J. A. (2009) Biosynthesis and biological screening of a genetically encoded library based on the cyclotide MCoTI-I. ChemBioChem 10, 2663-2670
30. Austin, J., Kimura, R. H., Woo, Y. H., and Camarero, J. A. (2010) In vivo biosynthesis of an Ala scan library based on the cyclic peptide SFTI-1. Amino Acids 38, 1313-1322
31. Garcia, A. E., Tai, K. P., Puttamadappa, S. S., Shekhtman, A., Ouellette, A. J., and Camarero, J. A. (2011) Biosynthesis and antimicrobial evaluation of backbone-cyclized α-defensins. Biochemistry 50, 10508-10519
32. 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
33. Young, T. S., Young, D. D., Ahmad, I., Louis, J. M., Benkovic, S. J., and Schultz, P. G. (2011) Evolution of cyclic peptide protease inhibitors. Proc. Natl. Acad. Sci. U.S.A. 108, 11052-11056
34. Deschuyteneer, G., Garcia, S., Michiels, B., Baudoux, B., Degand, H., Morsomme, P., and Soumillion, P. (2010) Intein-mediated cyclization of randomized peptides in the periplasm of Escherichia coli and their extracellular secretion. ACS Chem. Biol. 5, 691-700
35. Hackeng, T. M., Griffin, J. H., and Dawson, P. E. (1999) Protein synthesis by native chemical ligation: expanded scope by using straightforward methodology. Proc. Natl. Acad. Sci. U.S.A. 96, 10068-10073 (Pubitemid 29422513)
36. Tsukiji, S., and Nagamune, T. (2009) Sortase-mediated ligation: a gift from Gram-positive bacteria to protein engineering. ChemBioChem 10, 787-798
37. Parthasarathy, R., Subramanian, S., and Boder, E. T. (2007) Sortase A as a novel molecular "stapler" for sequence-specific protein conjugation. Bioconjug. Chem. 18, 469-476 (Pubitemid 46493518)
38. Antos, J. M., Popp, M. W., Ernst, R., Chew, G. L., Spooner, E., and Ploegh, H. L. (2009) A straight path to circular proteins. J. Biol. Chem. 284, 16028-16036
39. Popp, M. W., Dougan, S. K., Chuang, T. Y., Spooner, E., and Ploegh, H. L. (2011) Sortase-catalyzed transformations that improve the properties of cytokines. Proc. Natl. Acad. Sci. U.S.A. 108, 3169-3174
40. Bolscher, J. G., Oudhoff, M. J., Nazmi, K., Antos, J. M., Guimaraes, C. P., Spooner, E., Haney, E. F., Garcia Vallejo, J. J., Vogel, H. J., van't Hof, W., Ploegh, H. L., and Veerman, E. C. (2011) Sortase A as a tool for high yield histatin cyclization. FASEB J. 25, 2650-2658
41. Marx, U. C., Korsinczky, M. L., Schirra, H. J., Jones, A., Condie, B., Otvos, L., Jr., and Craik, D. J. (2003) Enzymatic cyclization of a potent Bowman- Birk protease inhibitor, sunflower trypsin inhibitor-1, and solution structure of an acyclic precursor peptide. J. Biol. Chem. 278, 21782-21789 (Pubitemid 36792582)
42. Thongyoo, P., Roqué-Rosell, N., Leatherbarrow, R. J., and Tate, E. W. (2008) Chemical and biomimetic total syntheses of natural and engineered MCoTI cyclotides. Org. Biomo.l Chem. 6, 1462-1470 (Pubitemid 351469865)
43. Gillon, A. D., Saska, I., Jennings, C. V., Guarino, R. F., Craik, D. J., and Anderson, M. A. (2008) Biosynthesis of circular proteins in plants. Plant J. 53, 505-515 (Pubitemid 351172020)
44. Mylne, J. S., Colgrave, M. L., Daly, N. L., Chanson, A. H., Elliott, A. G., McCallum, E. J., Jones, A., and Craik, D. J. (2011) Albumins and their processing machinery are hijacked for cyclic peptides in sunflower. Nat. Chem. Biol. 7, 257-259
45. Goto, Y., Katoh, T., and Suga, H. (2011) Flexizymes for genetic code reprogramming. Nat. Protoc. 6, 779-790
46. Kawakami, T., Ohta, A., Ohuchi, M., Ashigai, H., Murakami, H., and Suga, H. (2009) Diverse backbone-cyclized peptides via codon reprogramming. Nat. Chem. Biol. 5, 888-890
47. Puttamadappa, S. S., Jagadish, K., Shekhtman, A., and Camarero, J. A. (2010) Backbone dynamics of cyclotide MCoTI-I free and complexed with trypsin. Angew. Chem. Int. Ed. Engl. 49, 7030-7034
48. Burz, D. S., Dutta, K., Cowburn, D., and Shekhtman, A. (2006) Mapping structural interactions using in-cell NMR spectroscopy (STINT-NMR). Nat. Methods 3, 91-93 (Pubitemid 43173306)
49. Camarero, J. A., Fushman, D., Sato, S., Giriat, I., Cowburn, D., Raleigh, D. P., and Muir, T. W. (2001) Rescuing a destabilized protein fold through backbone cyclization. J. Mol. Biol. 308, 1045-1062 (Pubitemid 32574376)
50. Gould, A., Li, Y., Majumder, S., Garcia, A. E., Carlsson, P., Shekhtman, A., and Camarero, J. A. (2012) Recombinant production of rhesus θ-defensin-1 using a bacterial expression system. Mol. Biosyst. 8, 1359-1365