Conjugation of Proteins by Installing BIO-Orthogonally Reactive Groups at Their N-Termini

PLoS ONE

Volumn 7, Issue 10, 2012, Pages

  Soundrarajan, Nagasundarapandian ^a   Sokalingam, Sriram ^a   Raghunathan, Govindan ^a   Budisa, Nediljko ^b   Paik, Hyun Jong ^a   Yoo, Tae Hyeon ^c   Lee, Sun Gu ^a  

^a Pusan National University   (South Korea)

^b TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

^c Ajou University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE; ALKYNE; AMINO ACID DERIVATIVE; AZIDE; GREEN FLUORESCENT PROTEIN; METHIONINE; PROPARGYLGLYCINE;

AMINO ACID SEQUENCE; AMINO TERMINAL SEQUENCE; ARTICLE; CATALYSIS; CONJUGATION; CONTROLLED STUDY; ELECTROSPRAY MASS SPECTROMETRY; GENE MUTATION; HYDROPHOBICITY; MUTAGENESIS; NONHUMAN; PROTEIN BINDING; PROTEIN ENGINEERING; PROTEIN EXPRESSION; PROTEIN FOLDING; PROTEIN FUNCTION; PROTEIN MODIFICATION; PROTEIN PROTEIN INTERACTION; PROTEIN STRUCTURE;

ALANINE; ALKYNES; CLICK CHEMISTRY; GLYCINE; GREEN FLUORESCENT PROTEINS; METHIONINE; PROTEINS;

EID: 84867325294     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0046741     Document Type: Article

References (34)

1. Merkel L, Beckmann HSG, Wittmann V, Budisa N, (2008) Efficient N-terminal glycoconjugation of proteins by the N-end rule. ChemBioChem 9: 1220-1224.
2. Saerens D, Huang L, Bonroy K, Muyldermans S, (2008) Antibody fragments as probe in biosensor development. Sensors 8: 4669-4686.
3. Tomizaki KY, Usui K, Mihara H, (2005) Protein-detecting microarrays: Current accomplishments and requirements. ChemBioChem 6: 783-799.
4. Baker DP, Lin EY, Lin K, Pellegrini M, Petter RC, et al. (2005) N-terminally PEGylated human interferon-β-1a with improved pharmacokinetic properties and in vivo efficacy in a melanoma angiogenesis model. Bioconj Chem 17: 179-188.
5. Budisa N, (2004) Prolegomena to future experimental efforts on genetic code engineering by expanding its amino acid repertoire. Angew Chem 43: 6426-6463.
6. Link AJ, Tirrell DA, (2005) Reassignment of sense codons in vivo. Methods 36: 291-298.
7. Merkel L, Cheburkin Y, Wiltschi B, Budisa N, (2007) In vivo chemoenzymatic control of N-terminal processing in recombinant human epidermal growth factor. ChemBioChem 8: 2227-2232.
8. Selvakumar E, Rameshkumar N, Lee S-G, Lee S-J, Park H-S, (2010) In vivo production of functional single-chain Fv fragment with an N-terminal-specific bio-orthogonal reactive group. ChemBioChem 11: 498-501.
9. Wang A, Winblade Nairn N, Johnson RS, Tirrell DA, Grabstein K, (2008) Processing of N-terminal unnatural amino acids in recombinant human interferon-β in Escherichia coli. ChemBioChem 9: 324-330.
10. Kiick KL, (2001) Incorporation of azides into recombinant proteins for chemoselective modification by the Staudinger ligation. Proc Natl Acad Sci USA 99: 19-24.
11. Link AJ, (2006) Discovery of aminoacyl-tRNA synthetase activity through cell-surface display of noncanonical amino acids. Proc Natl Acad Sci USA 103: 10180-10185.
12. Yoo TH, Tirrell DA, (2007) High-throughput screening for methionyl-tRNA synthetases that enable residue-specific incorporation of noncanonical amino acids into recombinant proteins in bacterial Cells. Angew Chem 46: 5340-5343.
13. Bloom JD, Labthavikul ST, Otey CR, Arnold FH, (2006) Protein stability promotes evolvability. Proc Natl Acad Sci USA 103: 5869-5874.
14. Nagasundarapandian S, Merkel L, Budisa N, Govindan R, Ayyadurai N, et al. (2010) Engineering protein sequence composition for folding robustness renders efficient noncanonical amino acid incorporations. ChemBioChem 11: 2521-2524.
15. Taverna DM, Goldstein RA, (2002) Why are proteins marginally stable? Proteins: Struct Funct Genet 46: 105-109.
16. Soundrarajan N, Edwardraja S, Lee S-G, Yun H, Ayyadurai N, (2012) Enhancing the productivity of soluble green fluorescent protein through methionine-residue specific consensus approach. Afr J Biotechnol 11: 1059-1064.
17. Ayyadurai N, Neelamegam R, Nagasundarapandian S, Edwardraja S, Park HS, et al. (2009) Importance of expression system in the production of unnatural recombinant proteins in Escherichia coli. Biotechnol Bioprocess Eng 14: 257-265.
18. Bessette PH, Mena MA, Nguyen AW, Daugherty PS (2003) Construction of designed protein libraries using gene assembly mutagenesis. 29-37.
19. Pédelacq J-D, Cabantous S, Tran T, Terwilliger TC, Waldo GS, (2006) Engineering and characterization of a superfolder green fluorescent protein. Nat Biotechnol 24: 79-88.
20. Ormö M, Cubitt AB, Kallio K, Gross LA, Tsien RY, et al. (1996) Crystal structure of the Aequorea victoria green fluorescent protein. Science 273: 1392-1395.
21. Reid BG, Flynn GC, (1997) Chromophore formation in green fluorescent protein. Biochemistry 36: 6786-6791.
22. Cormack BP, Valdivia RH, Falkow S, (1996) FACS-optimized mutants of the green fluorescent protein (GFP). Gene 173: 33-38.
23. Budisa N, Pal PP, Alefelder S, Birle P, Krywcun T, et al. (2004) Probing the role of tryptophans in Aequorea victoria green fluorescent proteins with an expanded genetic code. Biol Chem 385: 191-202.
24. Roodveldt C, Aharoni A, Tawfik DS, (2005) Directed evolution of proteins for heterologous expression and stability. Curr Opin Struct Biol 15: 50-56.
25. Tokuriki N, Stricher F, Schymkowitz J, Serrano L, Tawfik DS, (2007) The stability effects of protein mutations appear to be universally distributed. J Mol Biol 369: 1318-1332.
26. Andreas Crameri, Whitehorn EA, Tate E, Stemmer WP, (1996) Improved green fluorescent protein by molecular evolution using DNA shuffling. Nat Biotechnol 14: 315-318.
27. Yoo TH, Link AJ, Tirrell DA, (2007) Evolution of a fluorinated green fluorescent protein. Proc Natl Acad Sci USA 104: 13887-13890.
28. Teerawanichpan P, Hoffman T, Ashe P, Datla R, Selvaraj G, (2007) Investigations of combinations of mutations in the jellyfish green fluorescent protein (GFP) that afford brighter fluorescence, and use of a version (VisGreen) in plant, bacterial, and animal cells. Biochim Biophys Acta 1770: 1360-1368.
29. Ito Y, Suzuki M, Husimi Y, (1999) A novel mutant of green fluorescent protein with enhanced sensitivity for microanalysis at 488 nm excitation. Biochem Biophys Res Commun 264: 556-560.
30. Huisgen R, (1963) 1.3-Dipolare Cycloadditionen Rückschau und Ausblick. Angew Chem 75: 604-637.
31. Rostovtsev VV, Green LG, Fokin VV, Sharpless KB, (2002) A Stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angew Chem 41: 2596-2599.
32. Pavoor TV, Cho YK, Shusta EV, (2009) Development of GFP-based biosensors possessing the binding properties of antibodies. Proc Natl Acad Sci USA 106: 11895-11900.
33. Wang L, Brock A, Herberich B, Schultz PG, (2001) Expanding the genetic code of Escherichia coli. Science 292: 498-500.
34. Jean-Paul Boissel, Thomas J Kasper, Bunn HF, (1988) Cotranslational amino-terminal processing of cytosolic poteins. J Biol Chem 263: 8443-8449.