메뉴 건너뛰기




Volumn 22, Issue 7, 2011, Pages 1259-1263

Strain-promoted "click" chemistry for terminal labeling of DNA

Author keywords

[No Author keywords available]

Indexed keywords

COPPER COMPOUNDS; DNA; HEAVY IONS; HYDROCARBONS; OLIGONUCLEOTIDES; POLYMERASE CHAIN REACTION; SYNTHESIS (CHEMICAL);

EID: 79960603771     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc1003668     Document Type: Article
Times cited : (68)

References (48)
  • 1
    • 72849144434 scopus 로고    scopus 로고
    • Sequencing technologies - The next generation
    • Metzker, M. L. (2010) Sequencing technologies - the next generation Nat. Rev. Genet. 11, 31-46
    • (2010) Nat. Rev. Genet. , vol.11 , pp. 31-46
    • Metzker, M.L.1
  • 2
    • 53649106195 scopus 로고    scopus 로고
    • Next-generation DNA sequencing
    • Shendure, J. and Ji, H. (2008) Next-generation DNA sequencing Nat. Biotechnol. 26, 1135-1145
    • (2008) Nat. Biotechnol. , vol.26 , pp. 1135-1145
    • Shendure, J.1    Ji, H.2
  • 3
    • 38049138721 scopus 로고    scopus 로고
    • Colloquium: Physical approaches to DNA sequencing and detection
    • Zwolak, M. and Di Ventra, M. (2008) Colloquium: Physical approaches to DNA sequencing and detection Rev. Mod. Phys. 80, 141
    • (2008) Rev. Mod. Phys. , vol.80 , pp. 141
    • Zwolak, M.1    Di Ventra, M.2
  • 4
    • 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
  • 5
    • 0027164483 scopus 로고
    • The synthesis of modified oligonucleotides by the phosphoramidite approach and their applications
    • Beaucage, S. L. and Iyer, R. P. (1993) The synthesis of modified oligonucleotides by the phosphoramidite approach and their applications Tetrahedron 49, 6123-6194
    • (1993) Tetrahedron , vol.49 , pp. 6123-6194
    • Beaucage, S.L.1    Iyer, R.P.2
  • 6
    • 0032918256 scopus 로고    scopus 로고
    • Nucleic acid detection technologies - Labels, strategies, and formats
    • Kricka, L. J. (1999) Nucleic acid detection technologies - labels, strategies, and formats Clin. Chem. 45, 453-458 (Pubitemid 29165953)
    • (1999) Clinical Chemistry , vol.45 , Issue.4 , pp. 453-458
    • Kricka, L.J.1
  • 7
    • 0037090917 scopus 로고    scopus 로고
    • How to make a DNA chip
    • DOI 10.1002/1521-3773(20020415)41 :8<1276::AID-ANIE1276>3.0.CO;2-2
    • Pirrung, M. C. (2002) How to make a DNA chip Angew. Chem., Int. Ed. 41, 1276-1289 (Pubitemid 34437410)
    • (2002) Angewandte Chemie - International Edition , vol.41 , Issue.8 , pp. 1276-1289
    • Pirrung, M.C.1
  • 8
    • 33748853175 scopus 로고    scopus 로고
    • Special-purpose modifications and immobilized functional nucleic acids for biomolecular interactions
    • DOI 10.1007/b136673, Immobilisation of DNA on Chips II
    • Di Giusto, D. A. and King, G. C. (2005) Special-purpose modifications and immobilized functional nucleic acids for biomolecular interactions Top. Curr. Chem. 261, 131-168 (Pubitemid 44420790)
    • (2005) Topics in Current Chemistry , vol.261 , pp. 131-168
    • Di Giusto, D.A.1    King, G.C.2
  • 9
    • 0000096835 scopus 로고    scopus 로고
    • Click chemistry: Diverse chemical function from a few good reactions
    • Kolb, H. C., Finn, M. G., and Sharpless, K. B. (2001) Click chemistry: Diverse chemical function from a few good reactions Angew. Chem., Int. Ed. 40, 2004-2021
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 2004-2021
    • Kolb, H.C.1    Finn, M.G.2    Sharpless, K.B.3
  • 10
    • 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
  • 11
    • 51049094897 scopus 로고    scopus 로고
    • Cu-catalyzed azide - Alkyne cycloaddition
    • Meldal, M. and Tornøe, C. W. (2008) Cu-catalyzed azide - alkyne cycloaddition Chem. Rev. 108, 2952-3015
    • (2008) Chem. Rev. , vol.108 , pp. 2952-3015
    • Meldal, M.1    Tornøe, C.W.2
  • 12
    • 63749116659 scopus 로고    scopus 로고
    • Comparison of a nucleosidic vs non-nucleosidic postsynthetic "click" modification of DNA with base-labile fluorescent probes
    • Berndl, S., Herzig, N., Kele, P., Lachmann, D., Li, X., Wolfbeis, O. S., and Wagenknecht, H.-A. (2009) Comparison of a nucleosidic vs non-nucleosidic postsynthetic "click" modification of DNA with base-labile fluorescent probes Bioconjugate Chem. 20, 558-564
    • (2009) Bioconjugate Chem. , vol.20 , pp. 558-564
    • Berndl, S.1    Herzig, N.2    Kele, P.3    Lachmann, D.4    Li, X.5    Wolfbeis, O.S.6    Wagenknecht, H.-A.7
  • 14
    • 0037462409 scopus 로고    scopus 로고
    • Click chemistry to construct fluorescent oligonucleotides for DNA sequencing
    • Seo, T. S., Li, Z., Ruparel, H., and Ju, J. (2002) Click chemistry to construct fluorescent oligonucleotides for DNA sequencing J. Org. Chem. 68, 609-612
    • (2002) J. Org. Chem. , vol.68 , pp. 609-612
    • Seo, T.S.1    Li, Z.2    Ruparel, H.3    Ju, J.4
  • 15
    • 38949201273 scopus 로고    scopus 로고
    • Modification of DNA with octadiynyl side chains: Synthesis, base pairing, and formation of fluorescent coumarin dye conjugates of four nucleobases by the alkyne-azide "click" reaction
    • DOI 10.1021/bc700300f
    • Seela, F., Sirivolu, V. R., and Chittepu, P. (2007) Modification of DNA with octadiynyl side chains: Synthesis, base pairing, and formation of fluorescent coumarin dye conjugates of four nucleobases by the alkyne - azide "click" reaction Bioconjugate Chem. 19, 211-224 (Pubitemid 351213853)
    • (2008) Bioconjugate Chemistry , vol.19 , Issue.1 , pp. 211-224
    • Seela, F.1    Sirivolu, V.R.2    Chittepu, P.3
  • 16
    • 75349096354 scopus 로고    scopus 로고
    • Double click" reaction on 7-deazaguanine DNA: Synthesis and excimer fluorescence of nucleosides and oligonucleotides with branched side chains decorated with proximal pyrenes
    • Seela, F. and Ingale, S. A. (2009) Double click" reaction on 7-deazaguanine DNA: Synthesis and excimer fluorescence of nucleosides and oligonucleotides with branched side chains decorated with proximal pyrenes J. Org. Chem. 75, 284-295
    • (2009) J. Org. Chem. , vol.75 , pp. 284-295
    • Seela, F.1    Ingale, S.A.2
  • 17
    • 33748609388 scopus 로고    scopus 로고
    • Click chemistry as a reliable method for the high-density postsynthetic functionalization of alkyne-modified DNA
    • DOI 10.1021/ol0610946
    • 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 (Pubitemid 44378327)
    • (2006) Organic Letters , vol.8 , Issue.17 , pp. 3639-3642
    • Gierlich, J.1    Burley, G.A.2    Gramlich, P.M.E.3    Hammond, D.M.4    Carell, T.5
  • 22
    • 49249097455 scopus 로고    scopus 로고
    • Rapid and efficient DNA strand cross-linking by click chemistry
    • Kočalka, P., El-Sagheer, A. H., and Brown, T. (2008) Rapid and efficient DNA strand cross-linking by click chemistry ChemBioChem 9, 1280-1285
    • (2008) ChemBioChem , vol.9 , pp. 1280-1285
    • Kočalka, P.1    El-Sagheer, A.H.2    Brown, T.3
  • 23
    • 34249794857 scopus 로고    scopus 로고
    • Template-directed oligonucleotide strand ligation, covalent intramolecular DNA circularization and catenation using click chemistry
    • DOI 10.1021/ja070273v
    • Kumar, R., El-Sagheer, A., Tumpane, J., Lincoln, P., Wilhelmsson, L. M., and Brown, T. (2007) Template-directed oligonucleotide strand ligation, covalent intramolecular DNA circularization and catenation using click chemistry J. Am. Chem. Soc. 129, 6859-6864 (Pubitemid 46847528)
    • (2007) Journal of the American Chemical Society , vol.129 , Issue.21 , pp. 6859-6864
    • Kumar, R.1    El-Sagheer, A.2    Tumpane, J.3    Lincoln, P.4    Wilhelmsson, L.M.5    Brown, T.6
  • 24
    • 67849124661 scopus 로고    scopus 로고
    • Synthesis and polymerase chain reaction amplification of DNA strands containing an unnatural triazole linkage
    • El-Sagheer, A. H. and Brown, T. (2009) Synthesis and polymerase chain reaction amplification of DNA strands containing an unnatural triazole linkage J. Am. Chem. Soc. 131, 3958-3964
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 3958-3964
    • El-Sagheer, A.H.1    Brown, T.2
  • 25
    • 50249134308 scopus 로고    scopus 로고
    • Thermolytic release of covalently linked DNA oligonucleotides and their conjugates from controlled-pore glass at near neutral pH
    • Grajkowski, A., Cieślak, J., Kauffman, J. S., Duff, R. J., Norris, S., Freedberg, D. I., and Beaucage, S. L. (2008) Thermolytic release of covalently linked DNA oligonucleotides and their conjugates from controlled-pore glass at near neutral pH Bioconjugate Chem. 19, 1696 - 1706
    • (2008) Bioconjugate Chem. , vol.19 , pp. 1696-1706
    • Grajkowski, A.1    Cieślak, J.2    Kauffman, J.S.3    Duff, R.J.4    Norris, S.5    Freedberg, D.I.6    Beaucage, S.L.7
  • 26
    • 37549013666 scopus 로고    scopus 로고
    • New strategies for cyclization and bicyclization of oligonucleotides by click chemistry assisted by microwaves
    • Lietard, J., Meyer, A., Vasseur, J.-J., and Morvan, F. (2007) New strategies for cyclization and bicyclization of oligonucleotides by click chemistry assisted by microwaves J. Org. Chem. 73, 191-200
    • (2007) J. Org. Chem. , vol.73 , pp. 191-200
    • Lietard, J.1    Meyer, A.2    Vasseur, J.-J.3    Morvan, F.4
  • 29
    • 65249088437 scopus 로고    scopus 로고
    • Click-chemistry-conjugated oligo-angiomax in the two-dimensional DNA lattice and its interaction with thrombin
    • Chao, J., Huang, W.-Y., Wang, J., Xiao, S.-J., Tang, Y.-C., and Liu, J.-N. (2009) Click-chemistry-conjugated oligo-angiomax in the two-dimensional DNA lattice and its interaction with thrombin Biomacromolecules 10, 877-883
    • (2009) Biomacromolecules , vol.10 , pp. 877-883
    • Chao, J.1    Huang, W.-Y.2    Wang, J.3    Xiao, S.-J.4    Tang, Y.-C.5    Liu, J.-N.6
  • 30
  • 31
    • 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
  • 33
    • 77949863611 scopus 로고    scopus 로고
    • Cu-free click cycloaddition reactions in chemical biology
    • Jewett, J. C. and Bertozzi, C. R. (2010) Cu-free click cycloaddition reactions in chemical biology Chem. Soc. Rev. 39, 1272-1279
    • (2010) Chem. Soc. Rev. , vol.39 , pp. 1272-1279
    • Jewett, J.C.1    Bertozzi, C.R.2
  • 34
    • 66449121649 scopus 로고    scopus 로고
    • Fast, copper-free click chemistry: A convenient solid-phase approach to oligonucleotide conjugation
    • Singh, I., Vyle, J. S., and Heaney, F. (2009) Fast, copper-free click chemistry: A convenient solid-phase approach to oligonucleotide conjugation Chem. Commun. 3276-3278
    • (2009) Chem. Commun. , pp. 3276-3278
    • Singh, I.1    Vyle, J.S.2    Heaney, F.3
  • 35
    • 72949116732 scopus 로고    scopus 로고
    • Metal free, "click and click-click" conjugation of ribonucleosides and 2′-OMe oligoribonucleotides on the solid phase
    • Singh, I. and Heaney, F. (2010) Metal free, "click and click-click" conjugation of ribonucleosides and 2′-OMe oligoribonucleotides on the solid phase Org. Biomol. Chem. 8, 451-456
    • (2010) Org. Biomol. Chem. , vol.8 , pp. 451-456
    • Singh, I.1    Heaney, F.2
  • 36
    • 77953584996 scopus 로고    scopus 로고
    • High-density DNA functionalization by a combination of Cu-catalyzed and Cu-free click chemistry
    • Gutsmiedl, K., Fazio, D., and Carell, T. (2010) High-density DNA functionalization by a combination of Cu-catalyzed and Cu-free click chemistry Chem. - Eur. J. 16, 6877-6883
    • (2010) Chem. - Eur. J. , vol.16 , pp. 6877-6883
    • Gutsmiedl, K.1    Fazio, D.2    Carell, T.3
  • 37
    • 66149185300 scopus 로고    scopus 로고
    • Copper-free "click" modification of DNA via nitrile oxide - Norbornene 1,3-dipolar cycloaddition
    • Gutsmiedl, K., Wirges, C. T., Ehmke, V., and Carell, T. (2009) Copper-free "click" modification of DNA via nitrile oxide - norbornene 1,3-dipolar cycloaddition Org. Lett. 11, 2405-2408
    • (2009) Org. Lett. , vol.11 , pp. 2405-2408
    • Gutsmiedl, K.1    Wirges, C.T.2    Ehmke, V.3    Carell, T.4
  • 38
    • 0034756136 scopus 로고    scopus 로고
    • Regeneration of carbonyl compounds from the corresponding oximes
    • Corsaro, A., Chiacchio, U., and Pistarà, V. (2001) Regeneration of carbonyl compounds from the corresponding oximes Synthesis 2001, 1903-1931 (Pubitemid 32973183)
    • (2001) Synthesis , Issue.13 , pp. 1903-1931
    • Corsaro, A.1    Chiacchio, U.2    Pistara, V.3
  • 39
    • 9344227358 scopus 로고    scopus 로고
    • A strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems
    • DOI 10.1021/ja044996f
    • Agard, N. J., Prescher, J. A., and Bertozzi, C. R. (2004) A strain-promoted [3 + 2] azide - alkyne cycloaddition for covalent modification of biomolecules in living systems J. Am. Chem. Soc. 126, 15046-15047 (Pubitemid 39557262)
    • (2004) Journal of the American Chemical Society , vol.126 , Issue.46 , pp. 15046-15047
    • Agard, N.J.1    Prescher, J.A.2    Bertozzi, C.R.3
  • 40
    • 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
  • 41
    • 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
  • 43
    • 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
  • 45
    • 77953886288 scopus 로고
    • Zur Existenz niedergliedriger Cycloalkine, I
    • Wittig, G. and Krebs, A. (1961) Zur Existenz niedergliedriger Cycloalkine, I Chem. Ber. 94, 3260-3275
    • (1961) Chem. Ber. , vol.94 , pp. 3260-3275
    • Wittig, G.1    Krebs, A.2
  • 46
    • 84982074373 scopus 로고
    • Zur Existenz niedergliedriger Cycloalkine, VIII. Zur Bildung und Reaktivität von Cyclooctin
    • Wittig, G. and Dorsch, H.-L. (1968) Zur Existenz niedergliedriger Cycloalkine, VIII. Zur Bildung und Reaktivität von Cyclooctin Justus Liebigs Ann. Chem. 711, 46-54
    • (1968) Justus Liebigs Ann. Chem. , vol.711 , pp. 46-54
    • Wittig, G.1    Dorsch, H.-L.2
  • 47
    • 0024987443 scopus 로고
    • Biotinyl and phosphotyrosinyl phosphoramidite derivatives useful in the incorporation of multiple reporter groups on synthetic oligonucleotides
    • Misiura, K., Durrant, I., Evans, M. R., and Gait, M. J. (1990) Biotinyl and phosphotyrosinyl phosphoramidite derivatives useful in the incorporation of multiple reporter groups on synthetic oligonucleotides Nucleic Acids Res. 18, 4345-4354
    • (1990) Nucleic Acids Res. , vol.18 , pp. 4345-4354
    • Misiura, K.1    Durrant, I.2    Evans, M.R.3    Gait, M.J.4
  • 48
    • 33745379412 scopus 로고    scopus 로고
    • BEAMing: Single-molecule PCR on microparticles in water-in-oil emulsions
    • DOI 10.1038/nmeth898, PII N898
    • Diehl, F., Li, M., He, Y., Kinzler, K. W., Vogelstein, B., and Dressman, D. (2006) BEAMing: single-molecule PCR on microparticles in water-in-oil emulsions Nat. Methods 3, 551-559 (Pubitemid 43941774)
    • (2006) Nature Methods , vol.3 , Issue.7 , pp. 551-559
    • Diehl, F.1    Li, M.2    He, Y.3    Kinzler, K.W.4    Vogelstein, B.5    Dressman, D.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.