메뉴 건너뛰기




Volumn 44, Issue 9, 2011, Pages 762-773

Bioorthogonal chemistry for site-specific labeling and surface immobilization of proteins

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AZIDE; COPPER; FLUORESCENT DYE; IMMOBILIZED PROTEIN; OXIME; PHOSPHINE; PHOSPHINE DERIVATIVE; PROTEIN; RAB PROTEIN; RAB7 PROTEIN; RAS PROTEIN; SULFONAMIDE;

EID: 80053018151     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar200046h     Document Type: Article
Times cited : (157)

References (52)
  • 1
    • 84984752764 scopus 로고    scopus 로고
    • Assignment of protein function in the postgenomic era
    • Saghatelian, A.; Cravatt, B. F. Assignment of protein function in the postgenomic era Nat. Chem. Biol. 2005, 1, 130-142
    • (2005) Nat. Chem. Biol. , vol.1 , pp. 130-142
    • Saghatelian, A.1    Cravatt, B.F.2
  • 2
    • 33846807647 scopus 로고    scopus 로고
    • Site-specific protein modification: Advances and applications
    • DOI 10.1016/j.cbpa.2006.11.036, PII S1367593106001931
    • Foley, T. L.; Burkart, M. D. Site-specific protein modification: advances and applications Curr. Opin. Chem. Biol. 2007, 11, 12-19 (Pubitemid 46216132)
    • (2007) Current Opinion in Chemical Biology , vol.11 , Issue.1 , pp. 12-19
    • Foley, T.L.1    Burkart, M.D.2
  • 3
    • 78149373806 scopus 로고    scopus 로고
    • Probing protein function by chemical modification
    • Wu, Y. W.; Goody, R. S. Probing protein function by chemical modification J. Pept. Sci. 2010, 16, 514-523
    • (2010) J. Pept. Sci. , vol.16 , pp. 514-523
    • Wu, Y.W.1    Goody, R.S.2
  • 4
    • 56749104130 scopus 로고    scopus 로고
    • Fluorescent probes for super-resolution imaging in living cells
    • Fernandez-Suarez, M.; Ting, A. Y. Fluorescent probes for super-resolution imaging in living cells Nat. Rev. Mol. Cell Biol. 2008, 9, 929-943
    • (2008) Nat. Rev. Mol. Cell Biol. , vol.9 , pp. 929-943
    • Fernandez-Suarez, M.1    Ting, A.Y.2
  • 5
    • 0033500546 scopus 로고    scopus 로고
    • Orthogonal ligation strategies for peptide and protein
    • DOI 10.1002/(SICI)1097-0282(1999)51:5<311::AID-BIP2>3.0.CO;2-A
    • Tam, J. P.; Yu, Q. T.; Miao, Z. W. Orthogonal ligation strategies for peptide and protein Biopolymers 1999, 51, 311-332 (Pubitemid 30117292)
    • (1999) Biopolymers - Peptide Science Section , vol.51 , Issue.5 , pp. 311-332
    • Tam, J.P.1    Yu, Q.2    Miao, Z.3
  • 6
    • 57749121492 scopus 로고    scopus 로고
    • Chemoselective Ligation and Modification Strategies for Peptides and Proteins
    • Hackenberger, C. P. R.; Schwarzer, D. Chemoselective Ligation and Modification Strategies for Peptides and Proteins Angew. Chem., Int. Ed. 2008, 47, 10030-10074
    • (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 10030-10074
    • Hackenberger, C.P.R.1    Schwarzer, D.2
  • 7
    • 0031663369 scopus 로고    scopus 로고
    • The green fluorescent protein
    • DOI 10.1146/annurev.biochem.67.1.509
    • Tsien, R. Y. The green fluorescent protein Annu. Rev. Biochem. 1998, 67, 509-544 (Pubitemid 28411137)
    • (1998) Annual Review of Biochemistry , vol.67 , pp. 509-544
    • Tsien, R.Y.1
  • 8
    • 77951236321 scopus 로고    scopus 로고
    • Beyond the Canonical 20 Amino Acids: Expanding the Genetic Lexicon
    • Young, T. S.; Schultz, P. G. Beyond the Canonical 20 Amino Acids: Expanding the Genetic Lexicon J. Biol. Chem. 2010, 285, 11039-11044
    • (2010) J. Biol. Chem. , vol.285 , pp. 11039-11044
    • Young, T.S.1    Schultz, P.G.2
  • 9
    • 70349266046 scopus 로고    scopus 로고
    • Site specific protein labeling by enzymatic posttranslational modification
    • Sunbul, M.; Yin, J. Site specific protein labeling by enzymatic posttranslational modification Org. Biomol. Chem. 2009, 7, 3361-3371
    • (2009) Org. Biomol. Chem. , vol.7 , pp. 3361-3371
    • Sunbul, M.1    Yin, J.2
  • 10
    • 70349917806 scopus 로고    scopus 로고
    • Bioorthogonal Chemistry: Fishing for Selectivity in a Sea of Functionality
    • Sletten, E. M.; Bertozzi, C. R. Bioorthogonal Chemistry: Fishing for Selectivity in a Sea of Functionality Angew. Chem., Int. Ed. 2009, 48, 6974-6998
    • (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 6974-6998
    • Sletten, E.M.1    Bertozzi, C.R.2
  • 11
    • 0034677879 scopus 로고    scopus 로고
    • Cell surface engineering by a modified Staudinger reaction
    • DOI 10.1126/science.287.5460.2007
    • Saxon, E.; Bertozzi, C. R. Cell surface engineering by a modified Staudinger reaction Science 2000, 287, 2007-2010 (Pubitemid 30158675)
    • (2000) Science , vol.287 , Issue.5460 , pp. 2007-2010
    • Saxon, E.1    Bertozzi, C.R.2
  • 12
    • 0037099395 scopus 로고    scopus 로고
    • A stepwise huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes
    • DOI 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4
    • Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes Angew. Chem., Int. Ed. 2002, 41, 2596-2599 (Pubitemid 34803480)
    • (2002) Angewandte Chemie - International Edition , vol.41 , Issue.14 , pp. 2596-2599
    • Rostovtsev, V.V.1    Green, L.G.2    Fokin, V.V.3    Sharpless, K.B.4
  • 13
    • 0037012920 scopus 로고    scopus 로고
    • Peptidotriazoles on solid phase: [1,2,3]-Triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides
    • DOI 10.1021/jo011148j
    • Tornoe, C. W.; Christensen, C.; Meldal, M. Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides J. Org. Chem. 2002, 67, 3057-3064 (Pubitemid 34457265)
    • (2002) Journal of Organic Chemistry , vol.67 , Issue.9 , pp. 3057-3064
    • Tornoe, C.W.1    Christensen, C.2    Meldal, M.3
  • 14
    • 0027944205 scopus 로고
    • Synthesis of proteins by native chemical ligation
    • Dawson, P. E.; Muir, T. W.; Clarklewis, I.; Kent, S. B. H. Synthesis of proteins by native chemical ligation Science 1994, 266, 776-779 (Pubitemid 24359280)
    • (1994) Science , vol.266 , Issue.5186 , pp. 776-779
    • Dawson, P.E.1    Muir, T.W.2    Clark-Lewis, I.3    Kent, S.B.H.4
  • 15
    • 0037435022 scopus 로고    scopus 로고
    • Protein analysis on a proteomic scale
    • DOI 10.1038/nature01512
    • Phizicky, E.; Bastiaens, P. I. H.; Zhu, H.; Snyder, M.; Fields, S. Protein analysis on a proteomic scale Nature 2003, 422, 208-215 (Pubitemid 36362758)
    • (2003) Nature , vol.422 , Issue.6928 , pp. 208-215
    • Phizicky, E.1    Bastiaens, P.I.H.2    Zhu, H.3    Snyder, M.4    Fields, S.5
  • 17
    • 74349086418 scopus 로고    scopus 로고
    • Protein Biochips: Oriented Surface Immobilization of Proteins
    • Lin, P. C.; Weinrich, D.; Waldmann, H. Protein Biochips: Oriented Surface Immobilization of Proteins Macromol. Chem. Phys. 2010, 211, 136-144
    • (2010) Macromol. Chem. Phys. , vol.211 , pp. 136-144
    • Lin, P.C.1    Weinrich, D.2    Waldmann, H.3
  • 18
    • 21044443738 scopus 로고    scopus 로고
    • Protein-detecting microarrays: Current accomplishments and requirements
    • Tomizaki, K. Y.; Usui, K.; Mihara, H. Protein-detecting microarrays: Current accomplishments and requirements ChemBioChem 2005, 6, 783-799
    • (2005) ChemBioChem , vol.6 , pp. 783-799
    • Tomizaki, K.Y.1    Usui, K.2    Mihara, H.3
  • 19
    • 13844306318 scopus 로고    scopus 로고
    • Enzymatic activity on a chip: The critical role of protein orientation
    • DOI 10.1002/pmic.200400948
    • Cha, T.; Guo, A.; Zhu, X. Y. Enzymatic activity on a chip: The critical role of protein orientation Proteomics 2005, 5, 416-419 (Pubitemid 40262058)
    • (2005) Proteomics , vol.5 , Issue.2 , pp. 416-419
    • Cha, T.1    Quo, A.2    Zhu, X.-Y.3
  • 21
    • 0027715195 scopus 로고
    • Attempts to mimic docking processes of the immune system: Recognition-induced formation of protein multilayers
    • Muller, W.; Ringsdorf, H.; Rump, E.; Wildburg, G.; Zhang, X.; Angermaier, L.; Knoll, W.; Liley, M.; Spinke, J. Attempt to mimic docking processes of the immune-system-recognition-induced formation of protein multilayers Science 1993, 262, 1706-1708 (Pubitemid 24030089)
    • (1993) Science , vol.262 , Issue.5140 , pp. 1706-1708
    • Muller, W.1    Ringsdorf, H.2    Rump, E.3    Wildburg, G.4    Zhang, X.5    Angermaier, L.6    Knoll, W.7    Liley, M.8    Spinke, J.9
  • 22
    • 0345549549 scopus 로고    scopus 로고
    • Non-canonical amino acids in protein engineering
    • DOI 10.1016/j.copbio.2003.10.011
    • Link, A. J.; Mock, M. L.; Tirrell, D. A. Non-canonical amino acids in protein engineering Curr. Opin. Biotechnol. 2003, 14, 603-609 (Pubitemid 37518438)
    • (2003) Current Opinion in Biotechnology , vol.14 , Issue.6 , pp. 603-609
    • Link, A.J.1    Mock, M.L.2    Tirrell, D.A.3
  • 23
    • 0343177218 scopus 로고
    • On new organic phosphorus bonding III Phosphine methylene derivatives and phosphinimine
    • Staudinger, H.; Meyer, J. On new organic phosphorus bonding III Phosphine methylene derivatives and phosphinimine Helv. Chim. Acta 1919, 2, 635-646
    • (1919) Helv. Chim. Acta , vol.2 , pp. 635-646
    • Staudinger, H.1    Meyer, J.2
  • 28
    • 18144374551 scopus 로고    scopus 로고
    • Site-specific immobilization of proteins in a microarray using intein-mediated protein splicing
    • DOI 10.1016/j.bmcl.2005.03.079
    • Girish, A.; Sun, H. Y.; Yeo, D. S. Y.; Chen, G. Y. J.; Chua, T. K.; Yao, S. Q. Site-specific immobilization of proteins in a microarray using intein-mediated protein splicing Bioorg. Med. Chem. Lett. 2005, 15, 2447-2451 (Pubitemid 40614968)
    • (2005) Bioorganic and Medicinal Chemistry Letters , vol.15 , Issue.10 , pp. 2447-2451
    • Girish, A.1    Sun, H.2    Yeo, D.S.Y.3    Chen, G.Y.J.4    Chua, T.-K.5    Yao, S.Q.6
  • 29
    • 8844258757 scopus 로고    scopus 로고
    • Chemoselective attachment of biologically active proteins to surfaces by expressed protein ligation and its application for "protein chip" fabrication
    • DOI 10.1021/ja0456611
    • Camarero, J. A.; Kwon, Y.; Coleman, M. A. Chemoselective attachment of biologically active proteins to surfaces by expressed protein ligation and its application for "protein chip" fabrication J. Am. Chem. Soc. 2004, 126, 14730-14731 (Pubitemid 39532148)
    • (2004) Journal of the American Chemical Society , vol.126 , Issue.45 , pp. 14730-14731
    • Camarero, J.A.1    Kwon, Y.2    Coleman, M.A.3
  • 31
    • 0034605862 scopus 로고    scopus 로고
    • Ras - A molecular switch involved in tumor formation
    • Wittinghofer, A.; Waldmann, H. Ras-A molecular switch involved in tumor formation Angew. Chem., Int. Ed. 2000, 39, 4193-4214
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 4193-4214
    • Wittinghofer, A.1    Waldmann, H.2
  • 32
    • 34547172644 scopus 로고    scopus 로고
    • General method for site-specific protein immobilization by staudinger ligation
    • DOI 10.1021/bc0603034
    • Kalia, J.; Abbott, N. L.; Raines, R. T. General method for site-specific protein immobilization by staudinger ligation Bioconjugate Chem. 2007, 18, 1064-1069 (Pubitemid 47122625)
    • (2007) Bioconjugate Chemistry , vol.18 , Issue.4 , pp. 1064-1069
    • Kalia, J.1    Abbott, N.L.2    Raines, R.T.3
  • 33
    • 34247876268 scopus 로고    scopus 로고
    • Exploiting the substrate tolerance of farnesyltransferase for site-selective protein derivatization
    • DOI 10.1002/cbic.200600440
    • Nguyen, U. T. T.; Cramer, J.; Gomis, J.; Reents, R.; Gutierrez-Rodriguez, M.; Goody, R. S.; Alexandrov, K.; Waldmann, H. Exploiting the substrate tolerance of farnesyltransferase for site-selective protein derivatization ChemBioChem 2007, 8, 408-423 (Pubitemid 47183660)
    • (2007) ChemBioChem , vol.8 , Issue.4 , pp. 408-423
    • Nguyen, U.T.T.1    Cramer, J.2    Gomis, J.3    Reents, R.4    Gutierrez-Rodriguez, M.5    Goody, R.S.6    Alexandrov, K.7    Waldmann, H.8
  • 34
    • 0032587329 scopus 로고    scopus 로고
    • Zinc-catalyted sulfur alkylation: Insights from protein farnesyltransferase
    • DOI 10.1016/S1367-5931(99)80030-1
    • Hightower, K. E.; Fierke, C. A. Zinc-catalyzed sulfur alkylation: insights from protein farnesyltransferase Curr. Opin. Chem. Biol. 1999, 3, 176-181 (Pubitemid 29145784)
    • (1999) Current Opinion in Chemical Biology , vol.3 , Issue.2 , pp. 176-181
    • Hightower, K.E.1    Fierke, C.A.2
  • 37
    • 0036703508 scopus 로고    scopus 로고
    • Stereoselective organic reactions in water
    • Lindstrom, U. M. Stereoselective organic reactions in water Chem. Rev. 2002, 102, 2751-2771
    • (2002) Chem. Rev. , vol.102 , pp. 2751-2771
    • Lindstrom, U.M.1
  • 40
    • 2942575037 scopus 로고    scopus 로고
    • Structure of the Rab7:REP-1 complex: Insights into the mechanism of Rab prenylation and choroideremia disease
    • DOI 10.1016/j.cell.2004.05.017, PII S0092867404004970
    • Rak, A.; Pylypenko, O.; Niculae, A.; Pyatkov, K.; Goody, R. S.; Alexandrov, K. Structure of the Rab7: REP-1 complex: Insights into the mechanism of rab prenylation and choroideremia disease Cell 2004, 117, 749-760 (Pubitemid 38748891)
    • (2004) Cell , vol.117 , Issue.6 , pp. 749-760
    • Rak, A.1    Pylypenko, O.2    Niculae, A.3    Pyatkov, K.4    Goody, R.S.5    Alexandrov, K.6
  • 41
    • 65549159536 scopus 로고    scopus 로고
    • Efficient and Chemoselective Surface Immobilization of Proteins by Using Aniline-Catalyzed Oxime Chemistry
    • Lempens, E. H. M.; Helms, B. A.; Merkx, M.; Meijer, E. W. Efficient and Chemoselective Surface Immobilization of Proteins by Using Aniline-Catalyzed Oxime Chemistry ChemBioChem 2009, 10, 658-662
    • (2009) ChemBioChem , vol.10 , pp. 658-662
    • Lempens, E.H.M.1    Helms, B.A.2    Merkx, M.3    Meijer, E.W.4
  • 42
    • 61449097424 scopus 로고    scopus 로고
    • High-efficiency labeling of sialylated glycoproteins on living cells
    • Zeng, Y.; Ramya, T. N. C.; Dirksen, A.; Dawson, P. E.; Paulson, J. C. High-efficiency labeling of sialylated glycoproteins on living cells Nat. Methods 2009, 6, 207-209
    • (2009) Nat. Methods , vol.6 , pp. 207-209
    • Zeng, Y.1    Ramya, T.N.C.2    Dirksen, A.3    Dawson, P.E.4    Paulson, J.C.5
  • 44
    • 33746191914 scopus 로고    scopus 로고
    • Practical synthesis of amides from in situ generated copper(I) acetylides and sulfonyl azides
    • DOI 10.1002/anie.200503805
    • Cassidy, M. P.; Raushel, J.; Fokin, V. V. Practical synthesis of amides from in situ generated copper(I) acetylides and sulfonyl azides Angew. Chem., Int. Ed. 2006, 45, 3154-3157 (Pubitemid 44099042)
    • (2006) Angewandte Chemie - International Edition , vol.45 , Issue.19 , pp. 3154-3157
    • Cassidy, M.P.1    Raushel, J.2    Fokin, V.V.3
  • 45
    • 28044470302 scopus 로고    scopus 로고
    • Copper-catalyzed hydrative amide synthesis with terminal alkyne, sulfonyl azide, and water
    • DOI 10.1021/ja056399e
    • Cho, S. H.; Yoo, E. J.; Bae, L.; Chang, S. Copper-catalyzed hydrative amide synthesis with terminal alkyne, sulfonyl azide, and water J. Am. Chem. Soc. 2005, 127, 16046-16047 (Pubitemid 41689230)
    • (2005) Journal of the American Chemical Society , vol.127 , Issue.46 , pp. 16046-16047
    • Cho, S.H.1    Yoo, E.J.2    Bae, I.3    Chang, S.4
  • 47
    • 84980124864 scopus 로고
    • Information on unsaturated compounds II the addition of mercaptan to unsaturated hydrocarbon
    • Posner, T. Information on unsaturated compounds II The addition of mercaptan to unsaturated hydrocarbon Ber. Dtsch. Chem. Ges. 1905, 38, 646-657
    • (1905) Ber. Dtsch. Chem. Ges. , vol.38 , pp. 646-657
    • Posner, T.1
  • 51
    • 33746760427 scopus 로고    scopus 로고
    • Site-specific, covalent attachment of proteins to a solid surface
    • DOI 10.1021/bc060125e
    • Duckworth, B. P.; Xu, J. H.; Taton, T. A.; Guo, A.; Distefano, M. D. Site-specific, covalent attachment of proteins to a solid surface Bioconjugate Chem. 2006, 17, 967-974 (Pubitemid 44162615)
    • (2006) Bioconjugate Chemistry , vol.17 , Issue.4 , pp. 967-974
    • Duckworth, B.P.1    Xu, J.2    Taton, T.A.3    Guo, A.4    Distefano, M.D.5
  • 52
    • 33746329936 scopus 로고    scopus 로고
    • Regio- and chemoselective covalent immobilization of proteins through unnatural amino acids
    • DOI 10.1021/ja061131o
    • Gauchet, C.; Labadie, G. R.; Poulter, C. D. Regio- and chemoselective covalent immobilization of proteins through unnatural amino acids J. Am. Chem. Soc. 2006, 128, 9274-9275 (Pubitemid 44117054)
    • (2006) Journal of the American Chemical Society , vol.128 , Issue.29 , pp. 9274-9275
    • Gauchet, C.1    Labadie, G.R.2    Poulter, C.D.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.