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Volumn 43, Issue 1, 2010, Pages 15-23

Copper-free click chemistry: Bioorthogonal reagents for tagging azides

Author keywords

3 + 2 cycloaddition; Azides; Bioorthogonal reagent; Click chemistry; Cyclooctynes

Indexed keywords


EID: 77953893928     PISSN: 00025100     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (72)

References (60)
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    • Phosphines and azides react to form azaylide intermediate 1. In the classic Staudinger reduction, pathway (a), the aza-ylide decomposes in the presence of water to afford a phosphine oxide and amine products. In the Staudinger ligation, pathway (b), the aza-ylide rearranges to form an amide bond and the corresponding phosphine oxide, while an alcohol is extruded
    • Phosphines and azides react to form azaylide intermediate 1. In the classic Staudinger reduction, pathway (a), the aza-ylide decomposes in the presence of water to afford a phosphine oxide and amine products. In the Staudinger ligation, pathway (b), the aza-ylide rearranges to form an amide bond and the corresponding phosphine oxide, while an alcohol is extruded.
  • 20
    • 9344227358 scopus 로고    scopus 로고
    • A correction of the rate constants was subsequently published by the same authors in J. Am. Chem. Soc. 2005, 127, 11196
    • Agard, N. J.; Prescher, J. A.; Bertozzi, C. R. J. Am. Chem. Soc. 2004, 126, 15046. A correction of the rate constants was subsequently published by the same authors in J. Am. Chem. Soc. 2005, 127, 11196.
    • (2004) J. Am. Chem. Soc , vol.127 , pp. 15046
    • Agard, N.J.1    Prescher, J.A.2    Bertozzi C., R.3
  • 30
    • 0001423135 scopus 로고
    • Angle Strained Cycloalkynes
    • Topics in Current Chemistry Series, Springer-Verlag: Berlin, Chapter 5
    • Krebs, A.; Wilke, J. Angle Strained Cycloalkynes. In Wittig Chemistry: Dedicated to Professor Dr. G. Wittig; Topics in Current Chemistry Series, Vol. 109; Springer-Verlag: Berlin, 1983; Chapter 5, pp 189-233.
    • (1983) Wittig Chemistry: Dedicated to Professor Dr. G. Wittig , vol.109 , pp. 189-233
    • Krebs, A.1    Wilke, J.2
  • 37
    • 43249099890 scopus 로고    scopus 로고
    • 4GalNAz to install azides into cell-surface mucin-type O-glycans, and, in the second step, the azide-labeled glycans are detected by reaction with a DIFO-fluorophore conjugate. Time-resolved populations of glycans can be visualized by an additional sequence of metabolic labeling and copper-free click chemistry using a spectrally distinct DIFO-fluorophore conjugate. Parts (D-H): Brightfield (D) and fluorescence (E-H) images of 3-day-old zebrafish embryos labeled as described in (C), with one hour of metabolic labeling in between the two copper-free click reactions. Part (E) Olfactory pit; (F-H) jaw epithelium. The red areas represent "old" glycans labeled with DIFO-647; the green areas represent "new" glycans labeled with DIFO-488
    • Laughlin, S. T.; Baskin, J. M.; Amacher, S. L.; Bertozzi, C. R. Science 2008, 320, 664. In Figure 2, Part (C) is a schematic depicting the strategy employed for imaging membrane-associated glycans in developing zebrafish. In the first step, zebrafish embryos are metabolically labeled with the azidosugar Ac4GalNAz to install azides into cell-surface mucin-type O-glycans, and, in the second step, the azide-labeled glycans are detected by reaction with a DIFO-fluorophore conjugate. Time-resolved populations of glycans can be visualized by an additional sequence of metabolic labeling and copper-free click chemistry using a spectrally distinct DIFO-fluorophore conjugate. Parts (D-H): Brightfield (D) and fluorescence (E-H) images of 3-day-old zebrafish embryos labeled as described in (C), with one hour of metabolic labeling in between the two copper-free click reactions. Part (E) Olfactory pit; (F-H) jaw epithelium. The red areas represent "old" glycans labeled with DIFO-647; the green areas represent "new" glycans labeled with DIFO-488.
    • (2008) Science , pp. 664
    • Laughlin, S.T.1    Baskin, J.M.2    Amacher, S.L.3    Bertozzi, C.R.4
  • 38
    • 36849084059 scopus 로고    scopus 로고
    • Target proteins (shown in purple in Figure 3)-engineered to contain a short lipoate acceptor peptide at one terminus-are site-specifically labeled with an azido lipoic acid analogue by the action of lipoic acid ligase (LplA). In a second step, the azide-labeled protein is detected by copper-free click chemistry using a cyclooctyne-fluorophore conjugate
    • Fernández-Suárez, M.; Baruah, H.; Martínez-Hernández, L.; Xie, K. T.; Baskin, J. M.; Bertozzi, C. R.; Ting, A. Y. Nat. Biotechnol. 2007, 25, 1483. Target proteins (shown in purple in Figure 3)-engineered to contain a short lipoate acceptor peptide at one terminus-are site-specifically labeled with an azido lipoic acid analogue by the action of lipoic acid ligase (LplA). In a second step, the azide-labeled protein is detected by copper-free click chemistry using a cyclooctyne-fluorophore conjugate.
    • (2007) Nat. Biotechnol , vol.25 , pp. 1483
    • Fernández-Suárez, M.1    Baruah, H.2    Martínez-Hernández, L.3    Xie, K.T.4    Baskin, J.M.5    Bertozzi, C.R.6    Ting, A.Y.7
  • 44
    • 64749111406 scopus 로고    scopus 로고
    • In Figure 4, azido- and cyclooctyne-containing analogues of pantetheine are chemoenzymatically appended onto separate NRPS polypeptide chains in place of the natural cofactor. Upon mixing of the two labeled NRPS polypeptides, a protein-protein interaction between communication-mediating (COM) domains (shown in green) brings the azide and cyclooctyne in proximity. The resultant triazole formation, which only occurs in the presence of a cognate COM domain pair, can be detected by polyacrylamide gel electrophoresis
    • Hur, G. H.; Meier, J. L.; Baskin, J.; Codelli, J. A.; Bertozzi, C. R.; Marahiel, M. A.; Burkart, M. D. Chem. Biol. 2009, 16, 372. In Figure 4, azido- and cyclooctyne-containing analogues of pantetheine are chemoenzymatically appended onto separate NRPS polypeptide chains in place of the natural cofactor. Upon mixing of the two labeled NRPS polypeptides, a protein-protein interaction between communication-mediating (COM) domains (shown in green) brings the azide and cyclooctyne in proximity. The resultant triazole formation, which only occurs in the presence of a cognate COM domain pair, can be detected by polyacrylamide gel electrophoresis.
    • (2009) Chem. Biol , vol.16 , pp. 372
    • Hur, G.H.1    Meier, J.L.2    Baskin, J.3    Codelli, J.A.4    Bertozzi, C.R.5    Marahiel, M.A.6    Burkart, M.D.7
  • 49
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    • In Figure 5, mixing, of soluble tetraazido star polymers (red) and biscyclooctyne- containing cross-linkers (blue) causes the formation of a 3D gel network (triazole linkages are shown in purple). The use of different star polymers and cross-linkers enables the modulation of gel properties (e.g., solubility, ability to be degraded by UV light, ability to be further functionalized post-gelation with imaging agents, drugs, or other probes). Incorporation of different cyclooctynes into the cross-linker (e.g., MOFO vs DIFO) allows for the tuning of gelation kinetics. See also reference 48
    • Johnson, J. A.; Baskin, J. M.; Bertozzi, C. R.; Koberstein, J. T.; Turro, N. J. Chem. Commun. 2008, 3064. In Figure 5, mixing of soluble tetraazido star polymers (red) and biscyclooctyne- containing cross-linkers (blue) causes the formation of a 3D gel network (triazole linkages are shown in purple). The use of different star polymers and cross-linkers enables the modulation of gel properties (e.g., solubility, ability to be degraded by UV light, ability to be further functionalized post-gelation with imaging agents, drugs, or other probes). Incorporation of different cyclooctynes into the cross-linker (e.g., MOFO vs DIFO) allows for the tuning of gelation kinetics. See also reference 48.
    • (2008) J. Chem. Commun , pp. 3064
    • Johnson, J.A.1    Baskin, J.M.2    Bertozzi, C.R.3    Koberstein, J.T.4    Turro, N.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.