Influence of global fluorination on chloramphenicol acetyltransferase activity and stability

Biotechnology and Bioengineering

Volumn 94, Issue 5, 2006, Pages 921-930

  Panchenko, Tatyana ^a   Zhu, Wan Wen ^a   Montclare, Jin Kim ^a,b  

^a POLYTECHNIC UNIVERSITY   (United States)

^b STATE UNIVERSITY OF NEW YORK   (United States)

Author keywords

Activity; Non natural amino acid; Protein engineering; Residue specific incorporation; Thermostability; Trifluoroleucine

Indexed keywords

BIOSYNTHESIS; CATALYST ACTIVITY; ENZYMES; ORGANIC SOLVENTS; SUBSTITUTION REACTIONS; THERMODYNAMIC STABILITY;

ACTIVITY; NON-NATURAL AMINO ACID; PROTEIN ENGINEERING; RESIDUE-SPECIFIC INCORPORATION; THERMOSTABILITY; TRIFLUOROLEUCINE;

AMINO ACIDS;

5',5',5' TRIFLUOROLEUCINE; CHLORAMPHENICOL ACETYLTRANSFERASE; LEUCINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CIRCULAR DICHROISM; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME STABILITY; ENZYME STRUCTURE; ENZYME SYNTHESIS; FLUORINATION; IN VITRO STUDY; IN VIVO STUDY; PROTEIN ENGINEERING; TEMPERATURE; THERMOSTABILITY;

CHLORAMPHENICOL O-ACETYLTRANSFERASE; ENZYME ACTIVATION; ENZYME STABILITY; ESCHERICHIA COLI; FLUORINE; LEUCINE; TEMPERATURE;

EID: 33746901302     PISSN: 00063592     EISSN: 10970290     Source Type: Journal    
DOI: 10.1002/bit.20910     Document Type: Article

References (48)

1. Arnold FH. 1993. Engineering proteins for non-natural environments. FASEB J 7(9):744-749.
2. Arnold FH. 1996. Directed evolution: Creating biocatalysts for the future. Chem Eng Sci 51(23):5091-5102.
3. Bilgiçer B, Kumar K. 2004. De novo design of defined helical bundles in membrane environments. Proc Natl Acad Sci USA 101:15324-15329.
4. Bilgiçer B, Fichera A, Kumar K. 2001a. A coiled coil with a fluorous core. J Am Chem Soc 123:4393-4399.
5. Bilgiçer B, Xing X, Kumar K. 2001b. Programmed self-sorting of coiled coils with leucine and hexafluoroleucine cores. J Am Chem Soc 123:11815-11816.
6. Budisa N. 2004. Prolegomena to future experimental efforts on genetic code engineering by expanding its amino acid repertoire. Angew Chem Int Ed 43:6426-6463.
7. Budisa N, Minks C, Medrano FJ, Lutz J, Huber R, Moroder L. 1998. Residue-specific bioincorporation of non-natural, biologically active amino acids into proteins as possible drug carriers: Structure and stability of the perthiaproline mutant of annexin V. Proc Natl Acad Sci USA 95:455-459.
8. Budisa N, Rubini M, Bae JH, Weyher E, Wenger W, Golbik R, Huber R, Moroder L. 2002. Global replacement of tryptophan with aminotryptophans generates non-invasive protein-based optical pH sensors. Angew Chem Int Ed 41:4066-4069.
9. Budisa N, Pipitone O, Siwanowicz I, Rubini M, Pal PP, Holak TA, Gelmi ML. 2004. Efforts towards the design of 'Teflon' proteins: In vivo translation with trifluorinated leucine and methionine analogues. Chem Biodiversity 1:1465-1475.
10. Chin JW, Cropp TA, Anderson JC, Mukherji M, Zhang ZW, Schultz PG. 2003a. An expanded eukaryotic genetic code. Science 301(5635):964-967.
11. Chin JW, Cropp TA, Chu S, Meggers E, Schultz PG. 2003b. Progress toward an expanded eukaryotic genetic code. Chem Biol 10(6):511-519.
12. Cirino PC, Tang Y, Takahashi K, Tirrell DA, Arnold FH. 2003. Global incorporation of norleucine in place of methionine in cytochrome P450 BM-3 heme domain increases peroxygenase activity. Biotechnol Bioeng 83:729-734.
13. Dolgikh DA, Kirpichnikov MP, Ptitsyn OB, Chemeris VV. 1996. Protein engineering of man-made proteins (a review). Mol Biol 30(2):149-156.
14. Ellis J, Bagshaw CR, Shaw WV. 1991. Substrate binding to chloramphenicol acetyltransferase-Evidence for negative cooperativity from equilibrium and kinetic constants for binary and ternary complexes. Biochemistry 30(44):10806-10813.
15. Fersht A, Winter G. 1992. Protein engineering. Trends Biochem Sci 17:292-294.
16. Frischauf AM, Lehrach H, Poustka A, Murray N. 1983. Lambda replacement vectors carrying polylinker sequences. J Mol Biol 170:827-842.
17. Furter R. 1998. Expansion of the genetic code: Site-directed p-fluorophenylalanine incorporation in Escherichia coli. Prot Sci 7:419-426.
18. Ibba M, Soll D. 2000. Aminoacyl-tRNA synthesis. Ann Rev Biochem 69:617-650.
19. Kiick KL, Tirrell DA. 2000. Protein engineering by in vivo incorporation of non-natural amino acids: Control of incorporation of methionine analogues by methionyl-tRNA synthetase. Tetrahedron 56:9487-9493.
20. Kiick KL, van Hest JCM, Tirrell DA. 2000. Expanding the scope of protein biosynthesis by altering the methionyl-tRNA synthetase activity of a bacterial expression host. Angew Chem Int Ed 39:2148-2152.
21. Kiick KL, Weberskirch R, Tirrell DA. 2001. Identification of an expanded set of translationally active methionine analogues in Escherichia coli. FEBS Lett 502:25-30.
22. Klibanov AM. 1997. Why are enzymes less active in organic solvents than in water? Trends Biotechnol 15:97-101.
23. Klibanov AM. 2000. Answering the question: 'Why did biocatalysis in organic media not take off in the 1930s?' Trends Biotechnol 18:85-86.
24. Kothakota S, Dougherty MJ, Fournier MJ, Mason TL, Yoshikawa E, Tirrell DA. 1995. Templated biological synthesis of polymers of abiological monomers. Macromol Symp 98:573-583.
25. Kukhar VP, Soloshonok VA, editors. 1995. Fluorine-containing amino acids: Synthesis and properties. New York: John Wiley and Sons.
26. Kwon I, Kirshenbaum K, Tirrell DA. 2003. Breaking the degeneracy of the genetic code. J Am Chem Soc 125:7512-7513.
27. Lee KH, Lee HY, Slutsky MM, Anderson JT, Marsh ENG. 2004. Fluorous effect in proteins: De novo design and characterization of a four-alpha-helix bundle protein containing hexafluoroleucine. Biochemistry 43(51):16277-16284.
28. Leslie AGW. 1990. Refined crystal structure of type III chloramphenicol acetyltransferase at 1.75 Å resolution. J Mol Biol 213:167-186.
29. Leslie AGW, Liddell JM, Shaw WV. 1986. Crystallization of a type-III chloramphenicol acetyltransferase. J Mol Biol 188:283-285.
30. Link AJ, Mock ML, Tirrell DA. 2003. Non-canonical amino acids in protein engineering. Curr Opin Biotech 14:603-609.
31. Marsh E. 2000. Towards the nonstick egg: Designing fluorous proteins. Chem Biol 7:R153-R157.
32. Minks C, Huber R, Moroder L, Budisa N. 2000. Noninvasive tracing of recombinant proteins with "fluorophenylalanine-fingers". Anal Biochem 284:29-34.
33. Moreau VH, da Silva AC, Siloto RMP, Valente AP, Leite A, Almeida FCL. 2004. The bZIP region of the plant transcription factor opaque-2 forms stable homodimers in solution and retains its helical structure upon subunit dissociation. Biochemistry 43(16):4862-4868.
34. Petka WA, Harden JL, McGrath KP, Wirtz D, Tirrell DA. 1998. Reversible hydrogels from self-assembling artificial proteins. Science 281(5375):389-392.
35. Rennert OM, Anker HS. 1963. On the incorporation of 5′, 5′, 5′-trifluoroleucine into proteins of E. coli. Biochemistry 2:471-476.
36. Sambrook J, Russell DW. 2001. Molecular cloning: A laboratory manual, 3rd edition. Cold Spring Harbor, NY: Cold Spring Harbor Laboratory Press.
37. Sharma N, Furter R, Kast P, Tirrell DA. 2000. Efficient introduction of aryl bromide functionality into proteins in vivo. FEBS Lett 467(1):37-40.
38. Shaw WV. 1975. Chloramphenicol acetyltransferase from chloramphenicol-resistant bacteria. Meth Enzymol 43:737-755.
39. Shaw WV. 1992. Chemical anatomy of antibiotic-resistance-Chloramphenicol acetyltransferase. Sci Prog 76(301-302):565-580.
40. Tang Y, Tirrell DA. 2001. Biosynthesis of a highly stable coiled-coil protein containing hexafluoroleucine in an engineered bacterial host. J Am Chem Soc 123:11089-11090.
41. Tang Y, Ghirlanda G, Petka WA, Nakajima T, DeGrado WF, Tirrell DA. 2001a. Fluorinated coiled-coil proteins prepared in vivo display enhanced thermal and chemical stability. Angew Chem Int Ed 40:1494-1497.
42. Tang Y, Ghirlanda G, Vaidehi N, Kua J, Mainz DT, Goddard WA, DeGrado WF, Tirrell DA. 2001b. Stabilization of coiled-coil peptide domains by introduction of trifluoroleucine. Biochemistry 40(9):2790-2796.
43. Wang L, Schultz PG. 2004. Expanding the genetic code. Angew Chem Int Ed 44:34-66.
44. Wang L, Brock A, Herberich B, Schultz PG. 2001. Expanding the genetic code of Escherichia coli. Science 292:498-500.
45. Wang P, Tang Y, Tirrell DA. 2003. Incorporation of trifluoroisoleucine into proteins in vivo. J Am Chem Soc 125:6900-6906.
46. Wang P, Fichera A, Kumar K, Tirrell DA. 2004. Alternative translations of a single RNA message: An identity switch of (2S, 3R)-4,4,4-trifluorovaline between valine and isoleucine codons. Angew Chem Int Ed 43:3664-3666.
47. Yu SJM, Tirrell DA. 2000. Thermal and structural properties of biologically derived monodisperse hairy-rod polymers. Biomacromolecules 1(3):310-312.
48. Zhang ZW, Gildersleeve J, Yang YY, Xu R, Loo JA, Uryu S, Wong CH, Schultz PG. 2004. A new strategy for the synthesis of glycoproteins. Science 303(5656):371-373.