메뉴 건너뛰기




Volumn 21, Issue 11, 2010, Pages 2076-2085

Surface functionalization using catalyst-free azide-alkyne cycloaddition

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; HYDROCARBONS; SOLUTIONS;

EID: 78649279718     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc100306u     Document Type: Article
Times cited : (203)

References (53)
  • 1
    • 70249112218 scopus 로고    scopus 로고
    • Orthogonal transformations on solid substrates: Efficient avenues to surface modification
    • Nebhani, L. and Barner-Kowollik, C. (2009) Orthogonal transformations on solid substrates: efficient avenues to surface modification Adv. Mater. 21, 3442-3468
    • (2009) Adv. Mater. , vol.21 , pp. 3442-3468
    • Nebhani, L.1    Barner-Kowollik, C.2
  • 2
    • 70349084150 scopus 로고    scopus 로고
    • Selective covalent protein immobilization: Strategies and applications
    • Wong, L. S., Khan, F., and Micklefield, J. (2009) Selective covalent protein immobilization: strategies and applications Chem. Rev. 109, 4025-4053
    • (2009) Chem. Rev. , vol.109 , pp. 4025-4053
    • Wong, L.S.1    Khan, F.2    Micklefield, J.3
  • 3
    • 73249130570 scopus 로고    scopus 로고
    • Applications of orthogonal "click" chemistries in the synthesis of functional soft materials
    • Iha, R. K., Wooley, K. L., Nyström, A. M., Burke, D. J., Kade, M. J., and Hawker, C. J. (2009) Applications of orthogonal "click" chemistries in the synthesis of functional soft materials Chem. Rev. 109, 5620-5686
    • (2009) Chem. Rev. , vol.109 , pp. 5620-5686
    • Iha, R.K.1    Wooley, K.L.2    Nyström, A.M.3    Burke, D.J.4    Kade, M.J.5    Hawker, C.J.6
  • 5
    • 55549122687 scopus 로고    scopus 로고
    • Patterning nanodomains with orthogonal functionalities: Solventless synthesis of self-sorting surfaces
    • Im, S. G., Bong, K. W., Kim, B.-S., Baxamusa, S. H., Hammond, P. T., Doyle, P. S., and Gleason, K. K. (2008) Patterning nanodomains with orthogonal functionalities: solventless synthesis of self-sorting surfaces J. Am. Chem. Soc. 130, 14424-14425
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 14424-14425
    • Im, S.G.1    Bong, K.W.2    Kim, B.-S.3    Baxamusa, S.H.4    Hammond, P.T.5    Doyle, P.S.6    Gleason, K.K.7
  • 7
    • 34547482973 scopus 로고    scopus 로고
    • Clicking polymers: A straightforward approach to novel macromolecular architectures
    • Fournier, D., Hoogenboom, R., and Schubert, U. S. (2007) Clicking polymers: a straightforward approach to novel macromolecular architectures Chem. Rev. Soc. 36, 1369-1380
    • (2007) Chem. Rev. Soc. , vol.36 , pp. 1369-1380
    • Fournier, D.1    Hoogenboom, R.2    Schubert, U.S.3
  • 8
    • 56449083251 scopus 로고    scopus 로고
    • Carbohydrate microarrays by microcontact "click" chemistry
    • Michel, O. and Ravoo, B. J. (2008) Carbohydrate microarrays by microcontact "click" chemistry Langmuir 24, 12116-12118
    • (2008) Langmuir , vol.24 , pp. 12116-12118
    • Michel, O.1    Ravoo, B.J.2
  • 9
    • 39749124166 scopus 로고    scopus 로고
    • Surface patterning with fluorescent molecules using click chemistry directed by scanning electrochemical microscopy
    • Ku, S.-Y., Wong, K.-T., and Bard, A. J. (2008) Surface patterning with fluorescent molecules using click chemistry directed by scanning electrochemical microscopy J. Am. Chem. Soc. 130, 2392-2393
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 2392-2393
    • Ku, S.-Y.1    Wong, K.-T.2    Bard, A.J.3
  • 10
    • 31544446908 scopus 로고    scopus 로고
    • Carbohydrate and protein immobilization onto solid surfaces by sequential diels-alder and azide-alkyne cycloadditions
    • Sun, X.-L., Stabler, C. L., Cazalis, C. S., and Chaikof, E. L. (2006) Carbohydrate and protein immobilization onto solid surfaces by sequential diels-alder and azide-alkyne cycloadditions Bioconjugate Chem. 17, 52-57
    • (2006) Bioconjugate Chem. , vol.17 , pp. 52-57
    • Sun, X.-L.1    Stabler, C.L.2    Cazalis, C.S.3    Chaikof, E.L.4
  • 11
    • 54249161798 scopus 로고    scopus 로고
    • Postsynthetic DNA modification through the copper-catalyzed azide-alkyne cycloaddition reaction
    • Gramlich, P. M. E., Wirges, C. T., Manetto, A., and Carell, T. (2008) Postsynthetic DNA modification through the copper-catalyzed azide-alkyne cycloaddition reaction Angew. Chem., Int. Ed. 47, 8350-8358
    • (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 8350-8358
    • Gramlich, P.M.E.1    Wirges, C.T.2    Manetto, A.3    Carell, T.4
  • 12
    • 56349111505 scopus 로고    scopus 로고
    • Novel strategies for the site-specific covalent labelling of nucleic acids
    • Weisbrod, S. H. and Marx, A. (2008) Novel strategies for the site-specific covalent labelling of nucleic acids Chem. Commun. 5675-5685
    • (2008) Chem. Commun. , pp. 5675-5685
    • Weisbrod, S.H.1    Marx, A.2
  • 13
    • 70349917806 scopus 로고    scopus 로고
    • Bioorthogonal chemistry: Fishing for selectivity in a sea of functionality
    • Sletten, E. and Bertozzi, C. (2009) Bioorthogonal chemistry: fishing for selectivity in a sea of functionality Angew. Chem., Int. Ed. 48, 6974-6998
    • (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 6974-6998
    • Sletten, E.1    Bertozzi, C.2
  • 15
    • 53849101862 scopus 로고    scopus 로고
    • Expeditious chemoenzymatic synthesis of homogeneous N-glycoproteins carrying defined oligosaccharide ligands
    • Ochiai, H., Huang, W., and Wang, L.-X. (2008) Expeditious chemoenzymatic synthesis of homogeneous N-glycoproteins carrying defined oligosaccharide ligands J. Am. Chem. Soc. 130, 13790-13803
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 13790-13803
    • Ochiai, H.1    Huang, W.2    Wang, L.-X.3
  • 16
    • 0037462106 scopus 로고    scopus 로고
    • Activity-based protein profiling in vivo using a copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition
    • Speers, A. E., Adam, G. C., and Cravatt, B. F. (2003) Activity-based protein profiling in vivo using a copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition J. Am. Chem. Soc. 125, 4686-4687
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 4686-4687
    • Speers, A.E.1    Adam, G.C.2    Cravatt, B.F.3
  • 17
    • 37549026429 scopus 로고    scopus 로고
    • Bioorthogonal click chemistry: Covalent labeling in living systems
    • Baskin, J. M. and Bertozzi, C. R. (2007) Bioorthogonal click chemistry: covalent labeling in living systems QSAR Comb. Sci. 26, 1211-1219
    • (2007) QSAR Comb. Sci. , vol.26 , pp. 1211-1219
    • Baskin, J.M.1    Bertozzi, C.R.2
  • 18
    • 0037099395 scopus 로고    scopus 로고
    • A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes
    • Rostovtsev, V. V., Green, L. G., Fokin, V. V., and Sharpless, K. B. (2002) A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes Angew. Chem., Int. Ed. 41, 2596-2599
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 2596-2599
    • Rostovtsev, V.V.1    Green, L.G.2    Fokin, V.V.3    Sharpless, K.B.4
  • 19
    • 77949796395 scopus 로고    scopus 로고
    • Copper-catalyzed azide-alkyne cycloaddition (CuAAC) and beyond: New reactivity of copper(I) acetylides
    • Hein, J. E. and Fokin, V. V. (2010) Copper-catalyzed azide-alkyne cycloaddition (CuAAC) and beyond: new reactivity of copper(I) acetylides Chem. Soc. Rev. 39, 1302-1315
    • (2010) Chem. Soc. Rev. , vol.39 , pp. 1302-1315
    • Hein, J.E.1    Fokin, V.V.2
  • 20
    • 77949786732 scopus 로고    scopus 로고
    • In situ click chemistry: Probing the binding landscapes of biological molecules
    • Mamidyala, S. K. and Finn, M. G. (2010) In situ click chemistry: probing the binding landscapes of biological molecules Chem. Soc. Rev. 39, 1252-1261
    • (2010) Chem. Soc. Rev. , vol.39 , pp. 1252-1261
    • Mamidyala, S.K.1    Finn, M.G.2
  • 21
    • 0037735344 scopus 로고    scopus 로고
    • Copper toxicity, oxidative stress, and antioxidant nutrients
    • Gaetke, L. M. and Chow, C. K. (2003) Copper toxicity, oxidative stress, and antioxidant nutrients Toxicology 189, 147-163
    • (2003) Toxicology , vol.189 , pp. 147-163
    • Gaetke, L.M.1    Chow, C.K.2
  • 22
    • 33748609388 scopus 로고    scopus 로고
    • Click chemistry as a reliable method for the high-density postsynthetic functionalization of alkyne-modified DNA
    • Gierlich, J., Burley, G. A., Gramlich, P. M. E., Hammond, D. M., and Carell, T. (2006) Click chemistry as a reliable method for the high-density postsynthetic functionalization of alkyne-modified DNA Org. Lett. 8, 3639-3642
    • (2006) Org. Lett. , vol.8 , pp. 3639-3642
    • Gierlich, J.1    Burley, G.A.2    Gramlich, P.M.E.3    Hammond, D.M.4    Carell, T.5
  • 23
    • 4243545125 scopus 로고    scopus 로고
    • Oxidative nucleobase modifications leading to strand scission
    • Burrows, C. J. and Muller, J. G. (1998) Oxidative nucleobase modifications leading to strand scission Chem. Rev. 98, 1109-1152
    • (1998) Chem. Rev. , vol.98 , pp. 1109-1152
    • Burrows, C.J.1    Muller, J.G.2
  • 25
    • 77951274251 scopus 로고    scopus 로고
    • Copper-free click chemistry for highly luminescent quantum dot conjugates: Application to in vivo metabolic imaging
    • Bernardin, A., Cazet, A. l., Guyon, L., Delannoy, P., Vinet, F., Bonnaff́, D., and Texier, I. (2010) Copper-free click chemistry for highly luminescent quantum dot conjugates: application to in vivo metabolic imaging Bioconjugate Chem 21, 583-588
    • (2010) Bioconjugate Chem , vol.21 , pp. 583-588
    • Bernardin, A.1    Cazet, A.I.2    Guyon, L.3    Delannoy, P.4    Vinet, F.5    Bonnaff́, D.6    Texier, I.7
  • 26
    • 77953886288 scopus 로고
    • On the existence of low-membered cycloalkynes
    • Wittig, G. and Krebs, A. (1961) On the existence of low-membered cycloalkynes Chem. Ber. 94, 3260-3275
    • (1961) Chem. Ber. , vol.94 , pp. 3260-3275
    • Wittig, G.1    Krebs, A.2
  • 27
    • 50249178663 scopus 로고    scopus 로고
    • Transition states of strain-promoted metal-free click chemistry: 1,3-dipolar cycloadditions of phenyl azide and cyclooctynes
    • Ess, D. H., Jones, G. O., and Houk, K. N. (2008) Transition states of strain-promoted metal-free click chemistry: 1,3-dipolar cycloadditions of phenyl azide and cyclooctynes Org. Lett. 10, 1633-1636
    • (2008) Org. Lett. , vol.10 , pp. 1633-1636
    • Ess, D.H.1    Jones, G.O.2    Houk, K.N.3
  • 29
    • 52049087165 scopus 로고    scopus 로고
    • A hydrophilic azacyclooctyne for Cu-free click chemistry
    • Sletten, E. M. and Bertozzi, C. R. (2008) A hydrophilic azacyclooctyne for Cu-free click chemistry Org. Lett. 10, 3097-3099
    • (2008) Org. Lett. , vol.10 , pp. 3097-3099
    • Sletten, E.M.1    Bertozzi, C.R.2
  • 30
    • 50249085119 scopus 로고    scopus 로고
    • Second-generation difluorinated cyclooctynes for copper-free click chemistry
    • Codelli, J. A., Baskin, J. M., Agard, N. J., and Bertozzi, C. R. (2008) Second-generation difluorinated cyclooctynes for copper-free click chemistry J. Am. Chem. Soc. 130, 11486-11493
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 11486-11493
    • Codelli, J.A.1    Baskin, J.M.2    Agard, N.J.3    Bertozzi, C.R.4
  • 31
    • 77949778625 scopus 로고    scopus 로고
    • Rapid Cu-free click chemistry with readily synthesized biarylazacyclooctynones
    • Jewett, J. C., Sletten, E. M., and Bertozzi, C. R. (2010) Rapid Cu-free click chemistry with readily synthesized biarylazacyclooctynones J. Am. Chem. Soc. 132, 3688-3690
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 3688-3690
    • Jewett, J.C.1    Sletten, E.M.2    Bertozzi, C.R.3
  • 32
    • 41049098451 scopus 로고    scopus 로고
    • Visualizing metabolically labeled glycoconjugates of living cells by copper-free and fast huisgen cycloadditions
    • Ning, X., Guo, J., Wolfert, M. A., and Boons, G.-J. (2008) Visualizing metabolically labeled glycoconjugates of living cells by copper-free and fast huisgen cycloadditions Angew. Chem., Int. Ed. 47, 2253-2255
    • (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 2253-2255
    • Ning, X.1    Guo, J.2    Wolfert, M.A.3    Boons, G.-J.4
  • 34
    • 33745892390 scopus 로고    scopus 로고
    • Discovery of aminoacyl-tRNA synthetase activity through cell-surface display of noncanonical amino acids
    • Link, A. J., Vink, M. K. S., Agard, N. J., Prescher, J. A., Bertozzi, C. R., and Tirrell, D. A. (2006) Discovery of aminoacyl-tRNA synthetase activity through cell-surface display of noncanonical amino acids Proc. Natl. Acad. Sci. U.S.A. 103, 10180-10185
    • (2006) Proc. Natl. Acad. Sci. U.S.A. , vol.103 , pp. 10180-10185
    • Link, A.J.1    Vink, M.K.S.2    Agard, N.J.3    Prescher, J.A.4    Bertozzi, C.R.5    Tirrell, D.A.6
  • 36
    • 53349168405 scopus 로고    scopus 로고
    • Cu-free cycloaddition for identifying catalytic active adenylation domains of nonribosomal peptide synthetases by phage display
    • Zou, Y. and Yin, J. (2008) Cu-free cycloaddition for identifying catalytic active adenylation domains of nonribosomal peptide synthetases by phage display Bioorg. Med. Chem. Lett. 18, 5664-5667
    • (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 5664-5667
    • Zou, Y.1    Yin, J.2
  • 38
    • 77649276989 scopus 로고    scopus 로고
    • Noncovalent cell surface engineering with cationic graft copolymers
    • Wilson, J. T., Krishnamurthy, V. R., Cui, W., Qu, Z., and Chaikof, E. L. (2010) Noncovalent cell surface engineering with cationic graft copolymers J. Am. Chem. Soc. 132, 2845-2845
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 2845-2845
    • Wilson, J.T.1    Krishnamurthy, V.R.2    Cui, W.3    Qu, Z.4    Chaikof, E.L.5
  • 40
    • 43249099890 scopus 로고    scopus 로고
    • In vivo imaging of membrane-associated glycans in developing zebrafish
    • Laughlin, S. T., Baskin, J. M., Amacher, S. L., and Bertozzi, C. R. (2008) In vivo imaging of membrane-associated glycans in developing zebrafish Science 320, 664-667
    • (2008) Science , vol.320 , pp. 664-667
    • Laughlin, S.T.1    Baskin, J.M.2    Amacher, S.L.3    Bertozzi, C.R.4
  • 42
    • 84981781132 scopus 로고
    • 5,6-Didehydro-11,12-dihydrodibenzo[a,e]-cyclooctene
    • Seitz, G., Pohl, L., and Pohlke, R. (1969) 5,6-Didehydro-11,12- dihydrodibenzo[a,e]-cyclooctene Angew. Chem., Int. Ed. 8, 447-448
    • (1969) Angew. Chem., Int. Ed. , vol.8 , pp. 447-448
    • Seitz, G.1    Pohl, L.2    Pohlke, R.3
  • 43
    • 0000976284 scopus 로고    scopus 로고
    • Desymmetrization reactions: Efficient preparation of unsymmetrically substituted linker molecules
    • Schwabacher, A. W., Lane, J. W., Schiesher, M. W., Leigh, K. M., and Johnson, C. W. (1998) Desymmetrization reactions: efficient preparation of unsymmetrically substituted linker molecules J. Org. Chem. 63, 1727-1729
    • (1998) J. Org. Chem. , vol.63 , pp. 1727-1729
    • Schwabacher, A.W.1    Lane, J.W.2    Schiesher, M.W.3    Leigh, K.M.4    Johnson, C.W.5
  • 44
    • 0035795079 scopus 로고    scopus 로고
    • An efficient and practical method for the synthesis of mono-N-protected a,w-diaminoalkanes
    • Lee, J. W., Jun, S. I., and Kim, K. (2001) An efficient and practical method for the synthesis of mono-N-protected a,w-diaminoalkanes Tetrahedron Lett. 42, 2709-2711
    • (2001) Tetrahedron Lett. , vol.42 , pp. 2709-2711
    • Lee, J.W.1    Jun, S.I.2    Kim, K.3
  • 45
    • 0035543976 scopus 로고    scopus 로고
    • Rearrangement of ammonium ylides produced by intramolecular reaction of catalytically generated metal carbenoids. Part 1. Synthesis of cyclic amines
    • Clark, J. S., Hodgson, P. B., Goldsmith, M. D., and Street, L. J. (2001) Rearrangement of ammonium ylides produced by intramolecular reaction of catalytically generated metal carbenoids. Part 1. Synthesis of cyclic amines J. Chem. Soc. Perkin Trans. 1, 3312-3324
    • (2001) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 3312-3324
    • Clark, J.S.1    Hodgson, P.B.2    Goldsmith, M.D.3    Street, L.J.4
  • 46
    • 78649284994 scopus 로고    scopus 로고
    • Preparation of cholesterol derivatives of peptidyl inhibitors of viral fusion
    • Pessi, A., Bianchi, E., and Ingallinella, P. (2009) Preparation of cholesterol derivatives of peptidyl inhibitors of viral fusion PCT Int. Appl. 39
    • (2009) PCT Int. Appl. , pp. 39
    • Pessi, A.1    Bianchi, E.2    Ingallinella, P.3
  • 47
    • 0025288944 scopus 로고
    • Avidin and streptavidin
    • Green, N. M. (1990) Avidin and streptavidin Methods Enzymol. 184, 51-67
    • (1990) Methods Enzymol. , vol.184 , pp. 51-67
    • Green, N.M.1
  • 48
    • 77952650680 scopus 로고    scopus 로고
    • Systems analysis of protein modification and cellular responses induced by electrophile stress
    • Jacobs, A. T. and Marnett, L. J. (2010) Systems analysis of protein modification and cellular responses induced by electrophile stress Acc. Chem. Res. 43, 673-683
    • (2010) Acc. Chem. Res. , vol.43 , pp. 673-683
    • Jacobs, A.T.1    Marnett, L.J.2
  • 49
    • 0025281379 scopus 로고
    • Introduction to avidin-biotin technology
    • Wilchek, M. and Bayer, E. A. (1990) Introduction to avidin-biotin technology Methods Enzymol. 184, 5-13
    • (1990) Methods Enzymol. , vol.184 , pp. 5-13
    • Wilchek, M.1    Bayer, E.A.2
  • 50
    • 77951965567 scopus 로고    scopus 로고
    • Surface-modified upconverting microparticles and nanoparticles for use in click chemistries
    • Mader, H. S., Link, M., Achatz, D. E., Uhlmann, K., Li, X., and Wolfbeis, O. S. (2010) Surface-modified upconverting microparticles and nanoparticles for use in click chemistries Chem.-Eur. J. 16, 5416-5424
    • (2010) Chem.-Eur. J. , vol.16 , pp. 5416-5424
    • Mader, H.S.1    Link, M.2    Achatz, D.E.3    Uhlmann, K.4    Li, X.5    Wolfbeis, O.S.6
  • 51
    • 77952571663 scopus 로고    scopus 로고
    • Showdomycin as a versatile chemical tool for the detection of pathogenesis-associated enzymes in bacteria
    • Böttcher, T. and Sieber, S. A. (2010) Showdomycin as a versatile chemical tool for the detection of pathogenesis-associated enzymes in bacteria J. Am. Chem. Soc. 132, 6964-6972
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 6964-6972
    • Böttcher, T.1    Sieber, S.A.2
  • 52
    • 76849105886 scopus 로고    scopus 로고
    • Synthesis and application of a new cleavable linker for "click"-based affinity chromatography
    • Landi, F., Johansson, C. M., Campopiano, D. J., and Hulme, A. N. (2010) Synthesis and application of a new cleavable linker for "click"-based affinity chromatography Org. Biomol. Chem. 8, 56-59
    • (2010) Org. Biomol. Chem. , vol.8 , pp. 56-59
    • Landi, F.1    Johansson, C.M.2    Campopiano, D.J.3    Hulme, A.N.4
  • 53
    • 69849099688 scopus 로고    scopus 로고
    • Bioconjugated Janus particles prepared by in situ click chemistry
    • Zhang, J., Wang, X., Wu, D., Liu, L., and Zhao, H. (2009) Bioconjugated Janus particles prepared by in situ click chemistry Chem. Mater. 21, 4012-4018
    • (2009) Chem. Mater. , vol.21 , pp. 4012-4018
    • Zhang, J.1    Wang, X.2    Wu, D.3    Liu, L.4    Zhao, H.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.