-
2
-
-
77953879604
-
-
Ellis, G. P., Luscombe, D. K., Eds., B. V.: Amesterdam, Chapter 3
-
Ellis, G. P., Luscombe, D. K., Eds.; Elsevier Science B. V.: Amesterdam, 1994; Vol. 31, Chapter 3, pp 121-232.
-
(1994)
Elsevier Science
, vol.31
, pp. 121-232
-
-
-
3
-
-
24044531286
-
-
Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem., Int. Ed. 2005, 44, 5188.
-
(2005)
Angew. Chem., Int. Ed
, vol.44
, pp. 5188
-
-
Bräse, S.1
Gil, C.2
Knepper, K.3
Zimmermann, V.4
-
5
-
-
77953881111
-
-
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.
-
-
-
-
6
-
-
4344704630
-
-
Prescher, J. A.; Dube, D. H.; Bertozzi, C. R. Nature 2004, 430, 873.
-
(2004)
Nature
, vol.430
, pp. 873
-
-
Prescher, J.A.1
Dube, D.H.2
Bertozzi, C.R.3
-
7
-
-
14744278308
-
-
Lin, F. L.; Hoyt, H. M.; van Halbeek, H.; Bergman, R. G.; Bertozzi, C. R. J. Am. Chem. Soc. 2005, 127, 2686.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 2686
-
-
Lin, F.L.1
Hoyt, H.M.2
van Halbeek, H.3
Bergman, R.G.4
Bertozzi, C.R.5
-
10
-
-
0037099395
-
-
Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596.
-
(2002)
Angew. Chem., Int. Ed
, vol.41
, pp. 2596
-
-
Rostovtsev, V.V.1
Green, L.G.2
Fokin, V.V.3
Sharpless, K.B.4
-
11
-
-
0037012920
-
-
Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057.
-
(2002)
J. Org. Chem
, vol.67
, pp. 3057
-
-
Tornøe, C.W.1
Christensen, C.2
Meldal, M.3
-
12
-
-
0000096835
-
-
Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004.
-
(2001)
Angew. Chem., Int. Ed
, vol.40
, pp. 2004
-
-
Kolb, H.C.1
Finn, M.G.2
Sharpless, K.B.3
-
17
-
-
70349917806
-
-
Sletten, E. M.; Bertozzi, C. R. Angew. Chem., Int. Ed. 2009, 48, 6974.
-
(2009)
Angew. Chem., Int. Ed
, vol.48
, pp. 6974
-
-
Sletten, E.M.1
Bertozzi, C.R.2
-
19
-
-
0041487865
-
-
Turner, R. B.; Jarrett, A. D.; Goebel, P.; Mallon, B. J. J. Am. Chem. Soc. 1973, 95, 790.
-
(1973)
J. Am. Chem. Soc
, vol.95
, pp. 790
-
-
Turner, R.B.1
Jarrett, A.D.2
Goebel, P.3
Mallon B., J.4
-
20
-
-
9344227358
-
-
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
-
22
-
-
33750995248
-
-
Laughlin, S. T.; Agard, N. J.; Baskin, J. M.; Carrico, I. S.; Chang, P. V.; Ganguli, A. S.; Hangauer, M. J.; Lo, A.; Prescher, J. A.; Bertozzi, C. R. Methods Enzymol. 2006, 415, 230.
-
(2006)
R. Methods Enzymol
, vol.1970
, pp. 230
-
-
Laughlin, S.T.1
Agard, N.J.2
Baskin, J.M.3
Carrico, I.S.4
Chang, P.V.5
Ganguli, A.S.6
Hangauer, M.J.7
Lo, A.8
Prescher, J.A.9
Bertozzi, C.10
-
23
-
-
39049182281
-
-
Agard, N. J.; Baskin, J. M.; Prescher, J. A.; Lo, A.; Bertozzi, C. R. ACS Chem. Biol. 2006, 1, 644.
-
(2006)
ACS Chem. Biol
, vol.1
, pp. 644
-
-
Agard, N.J.1
Baskin, J.M.2
Prescher, J.A.3
Lo, A.4
Bertozzi, C.R.5
-
24
-
-
36749028242
-
-
® 33342 (nuclei)
-
® 33342 (nuclei).
-
(2007)
Proc. Natl. Acad. Sci. U.S.A
, pp. 16793
-
-
Baskin, J.M.1
Prescher, J.A.2
Laughlin, S.T.3
Agard, N.J.4
Chang, P.V.5
Miller, I.A.6
Lo, A.7
Codelli, J.A.8
Bertozzi, C.R.9
-
25
-
-
50249085119
-
-
Codelli, J. A.; Baskin, J. M.; Agard, N. J.; Bertozzi, C. R. J. Am. Chem. Soc. 2008, 130, 11486.
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 11486
-
-
Codelli, J.A.1
Baskin, J.M.2
Agard, N.J.3
Bertozzi, C.R.4
-
26
-
-
11344284526
-
-
Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. II 1987, S1.
-
(1987)
J. Chem. Soc., Perkin Trans. II
-
-
Allen, F.H.1
Kennard, O.2
Watson, D.G.3
Brammer, L.4
Orpen, A.G.5
Taylor, R.6
-
27
-
-
50249178663
-
-
Ess, D. H.; Jones, G. O.; Houk, K. N. Org. Lett. 2008, 10, 1633.
-
(2008)
Org. Lett
, vol.10
, pp. 1633
-
-
Ess, D.H.1
Jones, G.O.2
Houk, K.N.3
-
28
-
-
67650558411
-
-
Schoenebeck, F.; Ess, D. H.; Jones, G. O.; Houk, K. N. J. Am. Chem. Soc. 2009, 131, 8121.
-
(2009)
J. Am. Chem. Soc
, vol.131
, pp. 8121
-
-
Schoenebeck, F.1
Ess, D.H.2
Jones, G.O.3
Houk, K.N.4
-
30
-
-
0001423135
-
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
-
31
-
-
84981781132
-
-
Seitz, G.; Pohl, L.; Pohlke, R. Angew. Chem., Int. Ed. 1969, 8, 447.
-
(1969)
Angew. Chem., Int. Ed
, vol.8
, pp. 447
-
-
Seitz, G.1
Pohl, L.2
Pohlke, R.3
-
32
-
-
41049098451
-
-
Ning, X.; Guo, J.; Wolfert, M. A.; Boons, G.-J. Angew. Chem., Int. Ed. 2008, 47, 2253.
-
(2008)
Angew. Chem., Int. Ed
, vol.47
, pp. 2253
-
-
Ning, X.1
Guo, J.2
Wolfert, M.A.3
Boons, G.-J.4
-
33
-
-
70350645279
-
-
Poloukhtine, A. A.; Mbua, N. E.; Wolfert, M. A.; Boons, G.-J.; Popik, V. V. J. Am. Chem. Soc. 2009, 131, 15769.
-
(2009)
J. Am. Chem. Soc
, vol.131
, pp. 15769
-
-
Poloukhtine, A.A.1
Mbua, N.E.2
Wolfert, M.A.3
Boons, G.-J.4
Popik, V.V.5
-
35
-
-
76649119485
-
-
Chang, P. V.; Prescher, J. A.; Sletten, E. M.; Baskin, J. M.; Miller, I. A.; Agard, N. J.; Lo, A.; Bertozzi, C. R. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 1821.
-
(2010)
Proc. Natl. Acad. Sci. U.S.A
, vol.107
, pp. 1821
-
-
Chang, P.V.1
Prescher, J.A.2
Sletten, E.M.3
Baskin, J.M.4
Miller, I.A.5
Agard, N.J.6
Lo, A.7
Bertozzi, C.R.8
-
36
-
-
34548715186
-
-
Van Berkel, S. S.; Dirks, A. J.; Debets, M. F.; van Delft, F. L.; Cornelissen, J. J. L. M.; Nolte, R. J. M.; Rutjes, F. P. J. T. ChemBioChem 2007, 8, 1504.
-
(2007)
ChemBioChem
, vol.8
, pp. 1504
-
-
van Berkel, S.S.1
Dirks, A.J.2
Debets, M.F.3
van Delft, F.L.4
Cornelissen, J.J.L.M.5
Nolte, R.J.M.6
Rutjes, F.P.J.T.7
-
37
-
-
43249099890
-
-
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
-
-
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
-
39
-
-
54749129835
-
-
Baruah, H.; Puthenveetil, S.; Choi, Y.-A.; Shah, S.; Ting, A. Y. Angew. Chem., Int. Ed. 2008, 47, 7018.
-
(2008)
Angew. Chem., Int. Ed
, vol.47
, pp. 7018
-
-
Baruah, H.1
Puthenveetil, S.2
Choi, Y.-A.3
Shah, S.4
Ting, A.Y.5
-
40
-
-
60149106725
-
-
Neef, A. B.; Schultz, C. Angew. Chem., Int. Ed. 2009, 48, 1498.
-
(2009)
Angew. Chem., Int. Ed
, vol.48
, pp. 1498
-
-
Neef, A.B.1
Schultz, C.2
-
41
-
-
10044258626
-
-
Sivakumar, K.; Xie, F.; Cash, B. M.; Long, S.; Barnhill, H. N.; Wang, Q. Org. Lett. 2004, 6, 4603.
-
(2004)
Org. Lett
, vol.6
, pp. 4603
-
-
Sivakumar, K.1
Xie, F.2
Cash, B.M.3
Long, S.4
Barnhill, H.N.5
Wang, Q.6
-
42
-
-
33745892390
-
-
Link, A. J.; Vink, M. K. S.; Agard, N. J.; Prescher, J. A.; Bertozzi, C. R.; Tirrell, D. A. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 10180.
-
(2006)
Proc. Natl. Acad. Sci. U.S.A
, vol.103
, pp. 10180
-
-
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
-
44
-
-
64749111406
-
-
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
-
45
-
-
67650403796
-
-
Nessen, M. A.; Kramer, G.; Back, J.; Baskin, J. M.; Smeenk, L. E. J.; de Koning, L. J.; van Maarseveen, J. H.; de Jong, L.; Bertozzi, C. R.; Hiemstra, H.; de Koster, C. G. J. Proteome Res. 2009, 8, 3702.
-
(2009)
J. Proteome Res
, vol.8
, pp. 3702
-
-
Nessen, M.A.1
Kramer, G.2
Back, J.3
Baskin, J.M.4
Smeenk, L.E.J.5
de Koning, L.J.6
van Maarseveen, J.H.7
de Jong, L.8
Bertozzi, C.R.9
Hiemstra, H.10
de Koster, C.G.11
-
46
-
-
58249110588
-
-
Kele, P.; Mezo, G.; Achatz, D.; Wolfbeis, O. S. Angew. Chem., Int. Ed. 2009, 48, 344.
-
(2009)
Angew. Chem., Int. Ed
, vol.48
, pp. 344
-
-
Kele, P.1
Mezo, G.2
Achatz, D.3
Wolfbeis, O.S.4
-
47
-
-
70350540463
-
-
Achatz, D. E.; Mezo, G.; Kele, P.; Wolfbeis, O. S. ChemBioChem 2009, 10, 2316.
-
(2009)
S. ChemBioChem
, vol.10
, pp. 2316
-
-
Achatz, D.E.1
Mezo, G.2
Kele, P.3
Wolfbeis, O.4
-
48
-
-
69949134479
-
-
Lallana, E.; Fernandez-Megia, E.; Riguera, R. J. Am. Chem. Soc. 2009, 131, 5748.
-
(2009)
J. Am. Chem. Soc
, vol.131
, pp. 5748
-
-
Lallana, E.1
Fernandez-Megia, E.2
Riguera, R.3
-
49
-
-
46149125303
-
-
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
-
50
-
-
68849096820
-
-
DeForest, C. A.; Polizzotti, B. D.; Anseth, K. S. Nat. Mater. 2009, 8, 659.
-
(2009)
Nat. Mater
, vol.8
, pp. 659
-
-
Deforest, C.A.1
Polizzotti, B.D.2
Anseth, K.S.3
-
52
-
-
53849105464
-
-
Blackman, M. L.; Royzen, M.; Fox, J. M. J. Am. Chem. Soc. 2008, 130, 13518.
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 13518
-
-
Blackman, M.L.1
Royzen, M.2
Fox, J.M.3
-
53
-
-
58149099966
-
-
Devaraj, N. K.; Weissleder, R.; Hilderbrand, S. A. Bioconjugate Chem. 2008, 19, 2297.
-
(2008)
Bioconjugate Chem
, vol.19
, pp. 2297
-
-
Devaraj, N.K.1
Weissleder, R.2
Hilderbrand, S.A.3
-
54
-
-
63449127358
-
-
Pipkorn, R.; Waldeck, W.; Didinger, B.; Koch, M.; Mueller, G.; Wiessler, M.; Braun, K. J. Pept. Sci. 2009, 15, 235.
-
(2009)
J. Pept. Sci
, vol.15
, pp. 235
-
-
Pipkorn, R.1
Waldeck, W.2
Didinger, B.3
Koch, M.4
Mueller, G.5
Wiessler, M.6
Braun, K.7
-
55
-
-
70349925246
-
-
Devaraj, N. K.; Upadhyay, R.; Haun, J. B.; Hilderbrand, S. A.; Weissleder, R. Angew. Chem., Int. Ed. 2009, 48, 7013.
-
(2009)
Angew. Chem., Int. Ed
, vol.48
, pp. 7013
-
-
Devaraj, N.K.1
Upadhyay, R.2
Haun, J.B.3
Hilderbrand, S.A.4
Weissleder, R.5
-
56
-
-
66149185300
-
-
Gutsmiedl, K.; Wirges, C. T.; Ehmke, V.; Carell, T. Org. Lett. 2009, 11, 2405.
-
(2009)
Org. Lett
, vol.11
, pp. 2405
-
-
Gutsmiedl, K.1
Wirges, C.T.2
Ehmke, V.3
Carell, T.4
-
58
-
-
42249110717
-
-
Song, W.; Wang, Y.; Qu, J.; Madden, M. M.; Lin, Q. Angew. Chem., Int. Ed. 2008, 47, 2832.
-
(2008)
Angew. Chem., Int. Ed
, vol.47
, pp. 2832
-
-
Song, W.1
Wang, Y.2
Qu, J.3
Madden, M.M.4
Lin, Q.5
-
59
-
-
48249141055
-
-
Song, W.; Wang, Y.; Qu, J.; Lin, Q. J. Am. Chem. Soc. 2008, 130, 9654.
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 9654
-
-
Song, W.1
Wang, Y.2
Qu, J.3
Lin, Q.4
-
60
-
-
70349786296
-
-
Wang, Y.; Song, W.; Hu, W. J.; Lin, Q. Angew. Chem., Int. Ed. 2009, 48, 5330.
-
(2009)
Angew. Chem., Int. Ed
, vol.48
, pp. 5330
-
-
Wang, Y.1
Song, W.2
Hu, W.J.3
Lin, Q.4
|