Reprogramming the translation initiation for the synthesis of physiologically stable cyclic peptides

ACS Chemical Biology

Volumn 3, Issue 2, 2008, Pages 120-129

  Goto, Yuki ^a,b   Ohta, Atsushi ^a,b   Sako, Yusuke ^a,b   Yamagishi, Yusuke ^a,b   Murakami, Hiroshi ^a   Suga, Hiroaki ^a,b  

^a UNIVERSITY OF TOKYO   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CYCLOPEPTIDE; MESSENGER RNA; METHIONINE TRANSFER RNA; PEPTIDE G7 18NATE; PEPTIDE LIBRARY; SULFIDE; UNCLASSIFIED DRUG;

AMINO ACID TRANSPORT; ARTICLE; BIOTECHNOLOGICAL PROCEDURES; CHEMICAL BOND; CONTROLLED STUDY; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; GENETIC CODE; GENETIC ENGINEERING; PRIORITY JOURNAL; STRUCTURE ANALYSIS; TRANSLATION INITIATION;

AMINOACYLATION; CODON, INITIATOR; CYCLIZATION; MOLECULAR STRUCTURE; PEPTIDE CHAIN INITIATION, TRANSLATIONAL; PEPTIDE LIBRARY; PEPTIDES, CYCLIC; RIBOSOMES; RNA, TRANSFER, AMINO ACYL; RNA, TRANSFER, MET; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; TRANSFER RNA AMINOACYLATION;

EID: 38349027623     PISSN: 15548929     EISSN: None     Source Type: Journal    
DOI: 10.1021/cb700233t     Document Type: Article

References (38)

1. Kozak, M. (1983) Comparison of initiation of protein synthesis in procaryotes, eucaryotes, and organelles, Microbiol. Rev. 47, 1-45.
2. Gualerzi, C. O., and Pon, C. L. (1990) Initiation of mRNA translation in prokaryotes, Biochemistry 29, 5881-5889.
3. Gold, L. (1988) Posttranscriptional regulatory mechanisms in Escherichia coli, Annu. Rev. Biochem. 57, 199-233.
4. Varshney, U., and RajBhandary, U. L. (1990) Initiation of protein synthesis from a termination codon, Proc. Natl. Acad. Sci. U.S.A. 87, 1586-1590.
5. Chattapadhyay, R., Pelka, H., and Schulman, L. H. (1990) Initiation of in vivo protein synthesis with non-methionine amino acids, Biochemistry 29, 4263-4268.
6. Mamaev, S., Olejnik, J., Olejnik, E. K., and Rothschild, K. J. (2004) Cell-free N-terminal protein labeling using initiator suppressor tRNA, Anal. Biochem. 326, 25-32.
7. Olejnik, J., Gite, S., Mamaev, S., and Rothschild, K. J. (2005) N-terminal labeling of proteins using initiator tRNA, Methods 36, 252-260.
8. Giege, R., Sissler, M., and Florentz, C. (1998) Universal rules and idiosyncratic features in tRNA identity, Nucleic Acids Res. 26, 5017-5035.
9. Wang, L., Xie, J., and Schultz, P. G. (2006) Expanding the genetic code, Annu. Rev. Biophys. Biomol. Struct. 35, 225-249.
10. Hecht, S. M. (1992) Probing the Synthetic Capabilities of a Center of Biochemical Catalysis, Acc. Chem. Res. 25, 545-552.
11. Link, A. J., Mock, M. L., and Tirrell, D. A. (2003) Non-canonical amino acids in protein engineering, Curr. Opin. Biotechnol. 14, 603-609.
12. Hecht, S. M., Alford, B. L., Kuroda, Y., and Kitano, S. (1978) "Chemical aminoacylation" of tRNAs, J. Biol. Chem. 253, 4517-4520.
13. Forster, A. C., Tan, Z., Nalam, M. N., Lin, H., Qu, H., Cornish, V. W., and Blacklow, S. C. (2003) Programming peptidomimetic syntheses by translating genetic codes designed de novo, Proc. Natl. Acad. Sci. U.S.A. 100, 6353-6357.
14. Tan, Z., Forster, A. C., Blacklow, S. C., and Cornish, V. W. (2004) Amino acid backbone specificity of the Escherichia coli translation machinery, J. Am. Chem. Soc. 126, 12752-12753.
15. Tan, Z., Blacklow, S. C., Cornish, V. W., and Forster, A. C. (2005) De novo genetic codes and pure translation display, Methods 36, 279-290.
16. Frankel, A., Millward, S. W., and Roberts, R. W. (2003) Encodamers: unnatural peptide oligomers encoded in RNA, Chem. Biol. 10, 1043-1050.
17. Frankel, A., and Roberts, R. W. (2003) In vitro selection for sense codon suppression, RNA 9, 780-786.
18. Josephson, K., Hartman, M. C., and Szostak, J. W. (2005) Ribosomal synthesis of unnatural peptides, J. Am. Chem. Soc. 127, 11727-11735.
19. Seebeck, F. P., and Szostak, J. W. (2006) Ribosomal synthesis of dehydroalanine-containing peptides, J. Am. Chem. Soc. 128, 7150-7151.
20. Murakami, H., Ohta, A., Ashigai, H., and Suga, H. (2006) A highly flexible tRNA acylation method for non-natural polypeptide synthesis, Nat. Methods 3, 357-359.
21. Shimizu, Y., Inoue, A., Tomari, Y., Suzuki, T., Yokogawa, T., Nishikawa, K., and Ueda, T. (2001) Cell-free translation reconstituted with purified components, Nat. Biotechnol. 19, 751-755.
22. Murakami, H., Saito, H., and Suga, H. (2003) A versatile tRNA aminoacylation catalyst based on RNA, Chem. Biol. 10, 655-662.
23. Murakami, H., Kourouklis, D., and Suga, H. (2003) Using a solid-phase ribozyme aminoacylation system to reprogram the genetic code, Chem. Biol. 10, 1077-1084.
24. Brizzard, B. L., Chubet, R. G., and Vizard, D. L. (1994) Immunoaffinity purification of FLAG epitope-tagged bacterial alkaline phosphatase using a novel monoclonal antibody and peptide elution, Biotechniques 16, 730-735.
25. Schmitt, E., Panvert, M., Bianquet, S., and Mechulam, Y. (1998) Crystal structure of methionyl-tRNA(f)(Met) transformylase complexed with the initiator formylmethionyl-tRNA(f)(Met), EMBO J. 17, 6819-6826.
26. Li, Y., Ramesh, V., Mangroo, D., Taneja, C., and RajBhandary, U. L. (2000) Suppressor mutations in Escherichia coli methionyl-tRNA formyltransferase that compensate for the formylation defect of a mutant tRNA aminoacylated with lysine, Biochemistry 39, 8039-8046.
27. Grunewald, J., and Marahiel, M. A. (2006) Chemoenzymatic and template-directed synthesis of bioactive macrocyclic peptides, Microbiol. Mol. Biol. Rev. 70, 121-146.
28. Harris, J. I., and Roos, P. (1956) Amino-acid sequence of a melanophore-stimulating peptide, Nature 178, 90.
29. Takayasu, S., Sakurai, T., Iwasaki, S., Teranishi, H., Yamanaka, A., Williams, S. C., Iguchi, H., Kawasawa, Y. I., Ikeda, Y., Sakakibara, I., Ohno, K., Ioka, R. X., Murakami, S., Dohmae, N., Xie, J., Suda, T., Motoike, T., Ohuchi, T., Yanagisawa, M., and Sakai, J. (2006) A neuropeptide ligand of the G protein-coupled receptor GPR103 regulates feeding, behavioral arousal, and blood pressure in mice, Proc. Natl. Acad. Sci. U.S.A. 103, 7438-7443.
30. Pero, S. C., Oligino, L., Daly, R. J., Soden, A. L., Liu, C., Roller, P. P., Li, P., and Krag, D. N. (2002) Identification of novel nonphosphorylated ligands, which bind selectively to the SH2 domain of Grb7, J. Biol. Chem. 277, 11918-11926.
31. Tanaka, S., Pero, S. C., Taguchi, K., Shimada, M., Mori, M., Krag, D. N., and Arii, S. (2006) Specific peptide ligand for Grb7 signal transduction protein and pancreatic cancer metastasis, J. Natl. Cancer. Inst. 98, 491-498.
32. Pero, S. C., Shukla, G. S., Cookson, M. M., Flemer, S., Jr., and Krag, D. N. (2007) Combination treatment with Grb7 peptide and Doxorubicin or Trastuzumab (Herceptin) results in cooperative cell growth inhibition in breast cancer cells, Br. J. Cancer 96, 1520-1525.
33. Roberts, K. D., Lambert, J. N., Ede, N. J., and Bray, A. M. (1998) Efficient synthesis of thioether-based cyclic peptide libraries, Tetrahedron Lett. 39, 8357-8360.
34. Lung, F. D. T., King, C. R., and Roller, P. P. (1999) Development of non-phosphorylated cyclic thioether peptide binding to the Grb2-SH2 domain, Lett. Pept. Sci. 6, 45-49.
35. Yu, L., Lai, Y. H., Wade, J. V., and Coutts, S. M. (1998) A simple and efficient method for the syntheses of thioether cyclic peptides, Tetrahedron Lett. 39, 6633-6636.
36. Hanes, J., and Pluckthun, A. (1997) In vitro selection and evolution of functional proteins by using ribosome display, Proc. Natl. Acad. Sci. U.S.A. 94, 4937-4942.
37. Nemoto, N., Miyamoto-Sato, E., Husimi, Y., and Yanagawa, H. (1997) In vitro virus: bonding of mRNA bearing puromycin at the 3′-terminal end to the C-terminal end of its encoded protein on the ribosome in vitro, FEBS Lett. 414, 405-408.
38. Roberts, R. W., and Szostak, J. W. (1997) RNA-peptide fusions for the in vitro selection of peptides and proteins, Proc. Natl. Acad. Sci. U.S.A. 94, 12297-12302.