Synthesis of Polyester by Means of Genetic Code Reprogramming

Chemistry and Biology

Volumn 14, Issue 12, 2007, Pages 1315-1322

  Ohta, Atsushi ^a   Murakami, Hiroshi ^b   Higashimura, Eri ^a   Suga, Hiroaki ^a,b  

^a UNIVERSITY OF TOKYO   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

CHEMBIO; PROTEINS

Indexed keywords

BIOPOLYMER; FLAG PEPTIDE; HYDROXYACID; MESSENGER RNA; PEPTIDE; POLYESTER; TRANSFER RNA; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; CHEMISTRY; ESCHERICHIA COLI; GENETIC CODE; GENETICS; MASS SPECTROMETRY; METABOLISM; NUCLEOTIDE SEQUENCE; POLYACRYLAMIDE GEL ELECTROPHORESIS; RIBOSOME;

BASE SEQUENCE; BIOPOLYMERS; ELECTROPHORESIS, POLYACRYLAMIDE GEL; ESCHERICHIA COLI; GENETIC CODE; HYDROXY ACIDS; PEPTIDES; POLYESTERS; RIBOSOMES; RNA, MESSENGER; RNA, TRANSFER; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 37149000703     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2007.10.015     Document Type: Article

References (29)

1. Josephson K., Hartman M.C., and Szostak J.W. Ribosomal synthesis of unnatural peptides. J. Am. Chem. Soc. 127 (2005) 11727-11735
2. Forster A.C., Tan Z., Nalam M.N., Lin H., Qu H., Cornish V.W., and Blacklow S.C. Programming peptidomimetic syntheses by translating genetic codes designed de novo. Proc. Natl. Acad. Sci. USA 100 (2003) 6353-6357
3. Frankel A., Millward S.W., and Roberts R.W. Encodamers: unnatural peptide oligomers encoded in RNA. Chem. Biol. 10 (2003) 1043-1050
4. Merryman C., and Green R. Transformation of aminoacyl tRNAs for the in vitro selection of "drug-like" molecules. Chem. Biol. 11 (2004) 575-582
5. Kwon I., Kirshenbaum K., and Tirrell D.A. Breaking the degeneracy of the genetic code. J. Am. Chem. Soc. 125 (2003) 7512-7513
6. Seebeck F.P., and Szostak J.W. Ribosomal synthesis of dehydroalanine-containing peptides. J. Am. Chem. Soc. 128 (2006) 7150-7151
7. Ellman J.A., Mendel D., and Schultz P.G. Site-specific incorporation of novel backbone structures into proteins. Science 255 (1992) 197-200
8. Koh J.T., Cornish V.W., and Schultz P.G. An experimental approach to evaluating the role of backbone interactions in proteins using unnatural amino acid mutagenesis. Biochemistry 36 (1997) 11314-11322
9. Tan Z., Forster A.C., Blacklow S.C., and Cornish V.W. Amino acid backbone specificity of the Escherichia coli translation machinery. J. Am. Chem. Soc. 126 (2004) 12752-12753
10. England P.M., Lester H.A., and Dougherty D.A. Mapping disulfide connectivity using backbone ester hydrolysis. Biochemistry 38 (1999) 14409-14415
11. Fahnestock S., and Rich A. Synthesis by ribosomes of viral coat protein containing ester linkages. Nat. New Biol. 229 (1971) 8-10
12. Fahnestock S., and Rich A. Ribosome-catalyzed polyester formation. Science 173 (1971) 340-343
13. Millward S.W., Takahashi T.T., and Roberts R.W. A general route for post-translational cyclization of mRNA display libraries. J. Am. Chem. Soc. 127 (2005) 14142-14143
14. Murakami H., Ohta A., Ashigai H., and Suga H. A highly flexible tRNA acylation method for non-natural polypeptide synthesis. Nat. Methods 3 (2006) 357-359
15. Murakami H., Kourouklis D., and Suga H. Using a solid-phase ribozyme aminoacylation system to reprogram the genetic code. Chem. Biol. 10 (2003) 1077-1084
16. Murakami H., Saito H., and Suga H. A versatile tRNA aminoacylation catalyst based on RNA. Chem. Biol. 10 (2003) 655-662
17. Saito H., Kourouklis D., and Suga H. An in vitro evolved precursor tRNA with aminoacylation activity. EMBO J. 20 (2001) 1797-1806
18. Shimizu Y., Inoue A., Tomari Y., Suzuki T., Yokogawa T., Nishikawa K., and Ueda T. Cell-free translation reconstituted with purified components. Nat. Biotechnol. 19 (2001) 751-755
19. Forster A.C., Weissbach H., and Blacklow S.C. A simplified reconstitution of mRNA-directed peptide synthesis: activity of the ε enhancer and an unnatural amino acid. Anal. Biochem. 297 (2001) 60-70
20. Fahnestock S., Neumann H., Shashoua V., and Rich A. Ribosome-catalyzed ester formation. Biochemistry 9 (1970) 2477-2483
21. Bieling P., Beringer M., Adio S., and Rodnina M.V. Peptide bond formation does not involve acid-base catalysis by ribosomal residues. Nat. Struct. Mol. Biol. 13 (2006) 423-428
22. Derwenskus K.H., and Sprinzl M. Interaction of cinnamyl-tRNAPhe with Escherichia coli elongation factor Tu. FEBS Lett. 151 (1983) 143-147
23. LaRiviere F.J., Wolfson A.D., and Uhlenbeck O.C. Uniform binding of aminoacyl-tRNAs to elongation factor Tu by thermodynamic compensation. Science 294 (2001) 165-168
24. Asahara H., and Uhlenbeck O.C. The tRNA specificity of Thermus thermophilus EF-Tu. Proc. Natl. Acad. Sci. USA 99 (2002) 3499-3504
25. Cochella L., and Green R. Isolation of antibiotic resistance mutations in the rRNA by using an in vitro selection system. Proc. Natl. Acad. Sci. USA 101 (2004) 3786-3791
26. Dedkova L.M., Fahmi N.E., Golovine S.Y., and Hecht S.M. Enhanced D-amino acid incorporation into protein by modified ribosomes. J. Am. Chem. Soc. 125 (2003) 6616-6617
27. Dedkova L.M., Fahmi N.E., Golovine S.Y., and Hecht S.M. Construction of modified ribosomes for incorporation of D-amino acids into proteins. Biochemistry 45 (2006) 15541-15551
28. Dahn H., and Rotzler G. Unstable 1,1,2-enetriols as (probable) intermediates in the decarboxylation of α,β-diketo acids. J. Org. Chem. 56 (1991) 3080-3082
29. Deechongkit S., You S.L., and Kelly J.W. Synthesis of all nineteen appropriately protected chiral α-hydroxy acid equivalents of the α-amino acids for Boc solid-phase depsi-peptide synthesis. Org. Lett. 6 (2004) 497-500