화학공학소재연구정보센터
Macromolecular Research, Vol.17, No.6, 424-429, June, 2009
Biological Synthesis of Alkyne-terminated Telechelic Recombinant Protein
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In this study, we demonstrate that the biological unnatural amino acid incorporation method can be utilized in vivo to synthesize an alkyne-terminated telechelic protein. Synthesis of terminally-functionalized polymers such as telechelic polymers is recognized to be important, since they can be employed usefully in many areas of biology and material science, such as drug delivery, colloidal dispersion, surface modification, and formation of polymer network. The introduction of alkyne groups into polymeric material is particularly interesting since the alkyne group can be a linker to combine other materials using click chemistry. To synthesize the telechelic recombinant protein, we attempted to incorporate the L-homopropargylglycine into the recombinant GroES fragment by expressing the recombinant gene encoding Met at the codons for both N- and C-terminals of the protein in the Met auxotrophic E. coli via Hpg supplementation. The Hpg incorporation rate was investigated and the incorporation was confirmed by MALDI-TOF analysis of the telechelic recombinant protein.
  1. Wang J, Lozier J, Johnson G, Kirshner S, Verthelyi D, Pariser A, Shores E, Rosenberg A, Nature Biotech., 26, 901 (2008)
  2. Holmgren SK, Taylor KM, Bretscher LE, Raines RT, Nature, 392(6677), 666 (1998)
  3. Nishi Y, Uchiyama S, Doi M, Nishiuchi Y, Nakazawa T, Ohkubo T, Kobayashi Y, Biochemistry, 44, 6034 (2005)
  4. Hendrickson TL, de Crecy-Lagard V, Schimmel P, Annu. Rev. Biochem., 73, 147 (2005)
  5. Budisa N, Angew. Chem. Int. Edit., 43, 6426 (2004)
  6. Link AJ, Mock ML, Tirrell DA, Curr. Opin. Biotechnol., 14, 603 (2003)
  7. Link AJ, Tirrell DA, Methods, 36, 291 (2005)
  8. Yoo TH, Tirrell DA, Angew. Chem. Int. Ed., 46, 5340 (2007)
  9. Yoo TH, Link AJ, Tirrell DA, PNAS, 104, 13887 (2007)
  10. Liu CC, Schultz PG, Nature Biotech., 24, 1436 (2006)
  11. Budisa N, Angew. Chem. Int. Edit., 43, 6426 (2004)
  12. Ibba M, Soll D, Annu. Rev. Biochem., 69, 617 (2000)
  13. Kiick KL, van Hest JCM, Tirrell DA, Angew. Chem. Int. Edit., 39, 2148 (2000)
  14. Kiick KL, Tirrell DA, Tetrahedron, 56, 9487 (2000)
  15. Kiick KL, Weberskirch R, Tirrell DA, Febs Lett., 502, 25 (2001)
  16. van Hest JCM, Kiick KL, Tirrell DA, J. Am. Chem. Soc., 122(7), 1282 (2000)
  17. Link AJ, Tirrell DA, J. Am. Chem. Soc., 125(37), 11164 (2003)
  18. Rostovtsev VV, Green LG, Fokin VV, Sharpless KB, Angew. Chem. Int. Edit. Engl., 41, 2596 (2000)
  19. van Hest JCM, Kiick KL, Tirrell DA, J. Am. Chem. Soc., 122(7), 1282 (2000)
  20. Mock ML, Michon T, van Hest JCM, Tirrell DA, Chembiochem., 7, 83 (2000)
  21. Deming TJ, Fournier MJ, Mason TL, Tirrell DA, J. Macromol. Sci. A, 34, 2143 (1997)
  22. Hild G, Prog. Polym. Sci., 23, 1019 (1998)
  23. Lee SH, Park JS, Koo CM, Lim BK, Kim SO, Macromol. Res., 16(3), 261 (2008)
  24. Johnson JA, Lewis DR, Az DDDU, Finn MG, Koberstein JT, Turro NJ, J. Am. Chem. Soc., 128(20), 6564 (2006)
  25. Binder WH, Sachsenhofer R, Macromol. Rapid Commun., 28(1), 15 (2007)
  26. Kolb HC, Finn MG, Sharpless KB, Angew. Chem. Int. Ed., 40, 2004 (2001)
  27. Collman JP, Devaraj NK, Chidsey CED, Langmuir, 20(4), 1051 (2004)
  28. Moses JE, Moorhouse AD, Chem. Soc. Rev., 36, 1249 (2007)
  29. Sambrook J, Russel DW, Molecular cloning: A Laboratory manual, 213 (1989)
  30. Yi KS, Chung J, Park K, Kim K, Im S, Choi C, Im M, Kim U, Hybridomics, 23, 279 (2004)
  31. Matray TJ, Kool ET, Nature, 399(6737), 704 (1999)
  32. Kool ET, Biopolymers, 48, 3 (1998)
  33. Morales JC, Kool ET, Nature Struct. Biol., 5, 950 (1998)
  34. Lutz MJ, Horlacher J, Benner SA, Bioorg. Med. Chem. Lett., 8, 1149 (1998)
  35. Kim YB, Rhee YH, Lenz RW, J. Polym., 29, 894 (1997)
  36. Lenz RW, Kim YB, Fuller RC, Fems Microbiol. Rev., 103, 207 (1992)
  37. Park WH, Lenz RW, Goodwin S, Macromolecules, 31(5), 1480 (1998)