Finding the right (bioorthogonal) chemistry

ACS Chemical Biology

Volumn 9, Issue 3, 2014, Pages 592-605

  Patterson, David M ^a   Nazarova, Lidia A ^a   Prescher, Jennifer A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKYNE; AZIDE; COPPER; ELECTROPHILE; KETONE; NUCLEOPHILE; REACTIVE OXYGEN METABOLITE; TRIAZOLE;

ANALYTIC METHOD; BIOORTHOGONAL CHEMISTRY; CATALYST; CHEMICAL LABELING; CHEMICAL REACTION; CYCLOADDITION; DIPOLE; HUMAN; IN VITRO STUDY; IN VIVO STUDY; LIPOPHILICITY; NONHUMAN; PRIORITY JOURNAL; PROTEIN TARGETING; REVIEW; SIGNAL NOISE RATIO; SYNTHESIS; BIOCHEMISTRY; MEDICINAL CHEMISTRY; PROCEDURES;

BIOCHEMISTRY; CHEMISTRY TECHNIQUES, SYNTHETIC; CHEMISTRY, PHARMACEUTICAL; CYCLOADDITION REACTION;

EID: 84897010721     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/cb400828a     Document Type: Review

References (210)

1. Chang, P. V. and Bertozzi, C. R. (2012) Imaging beyond the proteome Chem. Commun. 48, 8864-8879
2. Prescher, J. A. and Bertozzi, C. R. (2005) Chemistry in living systems Nat. Chem. Biol. 1, 13-21
3. Giepmans, B. N., Adams, S. R., Ellisman, M. H., and Tsien, R. Y. (2006) The fluorescent toolbox for assessing protein location and function Science 312, 217-224
4. Scheck, R. A. and Schepartz, A. (2011) Surveying protein structure and function using bis-arsenical small molecules Acc. Chem. Res. 44, 654-665
5. Cornish, V. W., Hahn, K. M., and Schultz, P. G. (1996) Site-specific protein modification using a ketone handle J. Am. Chem. Soc. 118, 8150-8151
6. Sletten, E. M. and Bertozzi, C. R. (2009) Bioorthogonal chemistry: fishing for selectivity in a sea of functionality Angew. Chem., Int. Ed. 48, 6974-6998
7. Rideout, D. (1986) Self-assembling cytotoxins Science 233, 561-563
8. Shao, J. and Tam, J. P. (1995) Unprotected peptides as building-blocks for the synthesis of peptide dendrimers with oxime, hydrazone, and thiazolidine linkages J. Am. Chem. Soc. 117, 3893-3899
9. Zeng, Y., Ramya, T. N., Dirksen, A., Dawson, P. E., and Paulson, J. C. (2009) High-efficiency labeling of sialylated glycoproteins on living cells Nat. Methods 6, 207-209
10. Crisalli, P. and Kool, E. T. (2013) Water-soluble organocatalysts for hydrazone and oxime formation J. Org. Chem. 78, 1184-1189
11. Dirksen, A. and Dawson, P. E. (2008) Rapid oxime and hydrazone ligations with aromatic aldehydes for biomolecular labeling Bioconjugate Chem. 19, 2543-2548
12. Dutta, D., Pulsipher, A., Luo, W., and Yousaf, M. N. (2011) Synthetic chemoselective rewiring of cell surfaces: generation of three-dimensional tissue structures J. Am. Chem. Soc. 133, 8704-8713
13. Wang, L., Zhang, Z., Brock, A., and Schultz, P. G. (2003) Addition of the keto functional group to the genetic code of Escherichia coli Proc. Natl. Acad. Sci. U.S.A. 100, 56-61
14. Wang, L., Xie, J., and Schultz, P. G. (2006) Expanding the genetic code Annu. Rev. Biophys. Biomol. Struct. 35, 225-249
15. Mahal, L. K., Yarema, K. J., and Bertozzi, C. R. (1997) Engineering chemical reactivity on cell surfaces through oligosaccharide biosynthesis Science 276, 1125-1128
16. Chang, P. V., Prescher, J. A., Hangauer, M. J., and Bertozzi, C. R. (2007) Imaging cell surface glycans with bioorthogonal chemical reporters J. Am. Chem. Soc. 129, 8400-8401
17. Kalia, J. and Raines, R. T. (2008) Hydrolytic stability of hydrazones and oximes Angew. Chem., Int. Ed. 47, 7523-7526
18. Agarwal, P., van der Weijden, J., Sletten, E. M., Rabuka, D., and Bertozzi, C. R. (2013) A Pictet-Spengler ligation for protein chemical modification Proc. Natl. Acad. Sci. U.S.A. 110, 46-51
19. Agarwal, P., Kudirka, R., Albers, A. E., Barfield, R. M., de Hart, G. W., Drake, P. M., Jones, L. C., and Rabuka, D. (2013) Hydrazino-Pictet-Spengler ligation as a biocompatible method for the generation of stable protein conjugates Bioconjugate Chem. 24, 846-851
20. Schilling, C. I., Jung, N., Biskup, M., Schepers, U., and Brase, S. (2011) Bioconjugation via azide-Staudinger ligation: An overview Chem. Soc. Rev. 40, 4840-4871
21. Griffin, R. J. (1994) The medicinal chemistry of the azido group Prog. Med. Chem. 31, 121-232
22. Brase, S., Gil, C., Knepper, K., and Zimmermann, V. (2005) Organic azides: An exploding diversity of a unique class of compounds Angew. Chem., Int. Ed. 44, 5188-5240
23. Saxon, E. and Bertozzi, C. R. (2000) Cell surface engineering by a modified Staudinger reaction Science 287, 2007-2010
24. van Berkel, S. S., van Eldijk, M. B., and van Hest, J. C. (2011) Staudinger ligation as a method for bioconjugation Angew. Chem., Int. Ed. 50, 8806-8827
25. Prescher, J. A., Dube, D. H., and Bertozzi, C. R. (2004) Chemical remodelling of cell surfaces in living animals Nature 430, 873-877
26. Neves, A. A., Stockmann, H., Harmston, R. R., Pryor, H. J., Alam, I. S., Ireland-Zecchini, H., Lewis, D. Y., Lyons, S. K., Leeper, F. J., and Brindle, K. M. (2011) Imaging sialylated tumor cell glycans in vivo FASEB J. 25, 2528-2537
27. Hang, H. C., Geutjes, E. J., Grotenbreg, G., Pollington, A. M., Bijlmakers, M. J., and Ploegh, H. L. (2007) Chemical probes for the rapid detection of fatty-acylated proteins in mammalian cells J. Am. Chem. Soc. 129, 2744-2745
28. Kho, Y., Kim, S. C., Jiang, C., Barma, D., Kwon, S. W., Cheng, J., Jaunbergs, J., Weinbaum, C., Tamanoi, F., Falck, J., and Zhao, Y. (2004) A tagging-via-substrate technology for detection and proteomics of farnesylated proteins Proc. Natl. Acad. Sci. U.S.A. 101, 12479-12484
29. Kaewsapsak, P., Esonu, O., and Dube, D. H. (2013) Recruiting the host's immune system to target Helicobacter pylori 's surface glycans ChemBioChem 14, 721-726
30. Debets, M. F., van der Doelen, C. W., Rutjes, F. P., and van Delft, F. L. (2010) Azide: A unique dipole for metal-free bioorthogonal ligations ChemBioChem 11, 1168-1184
31. 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
32. 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
33. Huisgen, R. (1963) 1,3-Dipolar cycloadditions. Past and future Angew. Chem., Int. Ed. 2, 565-598
34. 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
35. Tornoe, C. W., Christensen, C., and Meldal, M. (2002) 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. 67, 3057-3064
36. Worrell, B. T., Malik, J. A., and Fokin, V. V. (2013) Direct evidence of a dinuclear copper intermediate in Cu(I)-catalyzed azide-alkyne cycloadditions Science 340, 457-460
37. Gramlich, P. M., 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
38. Salic, A. and Mitchison, T. J. (2008) A chemical method for fast and sensitive detection of DNA synthesis in vivo Proc. Natl. Acad. Sci. U.S.A. 105, 2415-2420
39. Dieterich, D. C., Lee, J. J., Link, A. J., Graumann, J., Tirrell, D. A., and Schuman, E. M. (2007) Labeling, detection and identification of newly synthesized proteomes with bioorthogonal non-canonical amino-acid tagging Nat. Protoc. 2, 532-540
40. Salisbury, C. M. and Cravatt, B. F. (2007) Click chemistry-led advances in high content functional proteomics QSAR Comb. Sci. 26, 1229-1238
41. Nessen, M. A., Kramer, G., Back, J., Baskin, J. M., Smeenk, L. E., de Koning, L. J., van Maarseveen, J. H., de Jong, L., Bertozzi, C. R., Hiemstra, H., and de Koster, C. G. (2009) Selective enrichment of azide-containing peptides from complex mixtures J. Proteome Res. 8, 3702-3711
42. Zaro, B. W., Hang, H. C., and Pratt, M. R. (2013) Incorporation of unnatural sugars for the identification of glycoproteins Methods Mol. Biol. 951, 57-67
43. Leonard, S. E. and Carroll, K. S. (2011) Chemical 'omics' approaches for understanding protein cysteine oxidation in biology Curr. Opin. Chem. Biol. 15, 88-102
44. 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
45. Willems, L. I., van der Linden, W. A., Li, N., Li, K. Y., Liu, N., Hoogendoorn, S., van der Marel, G. A., Florea, B. I., and Overkleeft, H. S. (2011) Bioorthogonal chemistry: Applications in activity-based protein profiling Acc. Chem. Res. 44, 718-729
46. Cravatt, B. F., Wright, A. T., and Kozarich, J. W. (2008) Activity-based protein profiling: from enzyme chemistry to proteomic chemistry Annu. Rev. Biochem. 77, 383-414
47. Bateman, L. A., Zaro, B. W., Miller, S. M., and Pratt, M. R. (2013) An alkyne-aspirin chemical reporter for the detection of aspirin-dependent protein modification in living cells J. Am. Chem. Soc. 135, 14568-73
48. Sletten, E. M. and Bertozzi, C. R. (2011) From mechanism to mouse: A tale of two bioorthogonal reactions Acc. Chem. Res. 44, 666-676
49. Jewett, J. C. and Bertozzi, C. R. (2010) Cu-free click cycloaddition reactions in chemical biology Chem. Soc. Rev. 39, 1272-1279
50. 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
51. Baskin, J. M., Prescher, J. A., Laughlin, S. T., Agard, N. J., Chang, P. V., Miller, I. A., Lo, A., Codelli, J. A., and Bertozzi, C. R. (2007) Copper-free click chemistry for dynamic in vivo imaging Proc. Natl. Acad. Sci. U.S.A. 104, 16793-16797
52. 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
53. Chang, P. V., Prescher, J. A., Sletten, E. M., Baskin, J. M., Miller, I. A., Agard, N. J., Lo, A., and Bertozzi, C. R. (2010) Copper-free click chemistry in living animals Proc. Natl. Acad. Sci. U.S.A. 107, 1821-1826
54. van den Bosch, S. M., Rossin, R., Renart Verkerk, P., Ten Hoeve, W., Janssen, H. M., Lub, J., and Robillard, M. S. (2013) Evaluation of strained alkynes for Cu-free click reaction in live mice Nucl. Med. Biol. 40, 415-423
55. Baskin, J. M., Dehnert, K. W., Laughlin, S. T., Amacher, S. L., and Bertozzi, C. R. (2010) Visualizing enveloping layer glycans during zebrafish early embryogenesis Proc. Natl. Acad. Sci. U.S.A. 107, 10360-10365
56. Ramil, C. P. and Lin, Q. (2013) Bioorthogonal chemistry: strategies and recent developments Chem. Commun. 49, 11007-11022
57. 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
58. Gordon, C. G., Mackey, J. L., Jewett, J. C., Sletten, E. M., Houk, K. N., and Bertozzi, C. R. (2012) Reactivity of biarylazacyclooctynones in copper-free click chemistry J. Am. Chem. Soc. 134, 9199-9208
59. Debets, M. F., van Berkel, S. S., Dommerholt, J., Dirks, A. T., Rutjes, F. P., and van Delft, F. L. (2011) Bioconjugation with strained alkenes and alkynes Acc. Chem. Res. 44, 805-815
60. Ning, X., Temming, R. P., Dommerholt, J., Guo, J., Ania, D. B., Debets, M. F., Wolfert, M. A., Boons, G. J., and van Delft, F. L. (2010) Protein modification by strain-promoted alkyne-nitrone cycloaddition Angew. Chem., Int. Ed. 49, 3065-3068
61. McKay, C. S., Blake, J. A., Cheng, J., Danielson, D. C., and Pezacki, J. P. (2011) Strain-promoted cycloadditions of cyclic nitrones with cyclooctynes for labeling human cancer cells Chem. Commun. 47, 10040-10042
62. Sanders, B. C., Friscourt, F., Ledin, P. A., Mbua, N. E., Arumugam, S., Guo, J., Boltje, T. J., Popik, V. V., and Boons, G. J. (2011) Metal-free sequential [3 + 2]-dipolar cycloadditions using cyclooctynes and 1,3-dipoles of different reactivity J. Am. Chem. Soc. 133, 949-957
63. Wendeln, C., Singh, I., Rinnen, S., Schulz, C., Arlinghaus, H. F., Burley, G. A., and Ravoo, B. J. (2012) Orthogonal, metal-free surface modification by strain-promoted azide-alkyne and nitrile oxide-alkene/alkyne cycloadditions Chem. Sci. 3, 2479-2484
64. McGrath, N. A. and Raines, R. T. (2012) Diazo compounds as highly tunable reactants in 1,3-dipolar cycloaddition reactions with cycloalkynes Chem. Sci. 3, 3237-3240
65. Chou, H. H. and Raines, R. T. (2013) Conversion of azides into diazo compounds in water J. Am. Chem. Soc. 135, 14936-14939
66. McKay, C. S., Chigrinova, M., Blake, J. A., and Pezacki, J. P. (2012) Kinetics studies of rapid strain-promoted [3 + 2]-cycloadditions of nitrones with biaryl-aza-cyclooctynone Org. Biomol. Chem. 10, 3066-3070
67. Yu, Z., Pan, Y., Wang, Z., Wang, J., and Lin, Q. (2012) Genetically encoded cyclopropene directs rapid, photoclick-chemistry-mediated protein labeling in mammalian cells Angew. Chem., Int. Ed. 51, 10600-10604
68. Song, W., Wang, Y., Yu, Z., Vera, C. I., Qu, J., and Lin, Q. (2010) A metabolic alkene reporter for spatiotemporally controlled imaging of newly synthesized proteins in mammalian cells ACS Chem. Biol. 5, 875-885
69. Song, W., Wang, Y., Qu, J., Madden, M. M., and Lin, Q. (2008) A photoinducible 1,3-dipolar cycloaddition reaction for rapid, selective modification of tetrazole-containing proteins Angew. Chem., Int. Ed. 47, 2832-2835
70. Blackman, M. L., Royzen, M., and Fox, J. M. (2008) Tetrazine ligation: Fast bioconjugation based on inverse-electron-demand Diels-Alder reactivity J. Am. Chem. Soc. 130, 13518-13519
71. Selvaraj, R. and Fox, J. M. (2013) trans -Cyclooctene-a stable, voracious dienophile for bioorthogonal labeling Curr. Opin Chem Biol. 17, 753-760
72. Bach, R. D. (2009) Ring strain energy in the cyclooctyl system. The effect of strain energy on [3 + 2] cycloaddition reactions with azides J. Am. Chem. Soc. 131, 5233-5243
73. Rossin, R., van den Bosch, S. M., Ten Hoeve, W., Carvelli, M., Versteegen, R. M., Lub, J., and Robillard, M. S. (2013) Highly reactive trans -cyclooctene tags with improved stability for Diels-Alder chemistry in living systems Bioconjugate Chem. 24, 1210-1217
74. Devaraj, N. K., Thurber, G. M., Keliher, E. J., Marinelli, B., and Weissleder, R. (2012) Reactive polymer enables efficient in vivo bioorthogonal chemistry Proc. Natl. Acad. Sci. U.S.A. 109, 4762-4767
75. Rossin, R., Verkerk, P. R., van den Bosch, S. M., Vulders, R. C., Verel, I., Lub, J., and Robillard, M. S. (2010) In vivo chemistry for pretargeted tumor imaging in live mice Angew. Chem., Int. Ed. 49, 3375-3378
76. Budin, G., Chung, H. J., Lee, H., and Weissleder, R. (2012) A magnetic gram stain for bacterial detection Angew. Chem., Int. Ed. 51, 7752-7755
77. Devaraj, N. K., Weissleder, R., and Hilderbrand, S. A. (2008) Tetrazine-based cycloadditions: Application to pretargeted live cell imaging Bioconjugate Chem. 19, 2297-2299
78. Karver, M. R., Weissleder, R., and Hilderbrand, S. A. (2011) Synthesis and evaluation of a series of 1,2,4,5-tetrazines for bioorthogonal conjugation Bioconjugate Chem. 22, 2263-2270
79. Seckute, J. and Devaraj, N. K. (2013) Expanding room for tetrazine ligations in the in vivo chemistry toolbox Curr. Opin. Chem. Biol. 17, 761-767
80. Yang, J., Seckute, J., Cole, C. M., and Devaraj, N. K. (2012) Live-cell imaging of cyclopropene tags with fluorogenic tetrazine cycloadditions Angew. Chem., Int. Ed. 51, 7476-7479
81. Patterson, D. M., Nazarova, L. A., Xie, B., Kamber, D. N., and Prescher, J. A. (2012) Functionalized cyclopropenes as bioorthogonal chemical reporters J. Am. Chem. Soc. 134, 18638-18643
82. Cole, C. M., Yang, J., Seckute, J., and Devaraj, N. K. (2013) Fluorescent live-cell imaging of metabolically incorporated unnatural cyclopropene- mannosamine derivatives ChemBioChem 14, 205-208
83. Yi, L., Sun, H., Wu, Y. W., Triola, G., Waldmann, H., and Goody, R. S. (2010) A highly efficient strategy for modification of proteins at the C terminus Angew. Chem., Int. Ed. 49, 9417-9421
84. Gilmore, J. M., Scheck, R. A., Esser-Kahn, A. P., Joshi, N. S., and Francis, M. B. (2006) N-terminal protein modification through a biomimetic transamination reaction Angew. Chem., Int. Ed. 45, 5307-5311
85. Scheck, R. A. and Francis, M. B. (2007) Regioselective labeling of antibodies through N-terminal transamination ACS Chem. Biol. 2, 247-251
86. Hermanson, G. T. (1996) Bioconjugate Techniques, Academic Press, San Diego.
87. Stephanopoulos, N. and Francis, M. B. (2011) Choosing an effective protein bioconjugation strategy Nat. Chem. Biol. 7, 876-884
88. Antos, J. M. and Francis, M. B. (2006) Transition metal catalyzed methods for site-selective protein modification Curr. Opin. Chem. Biol. 10, 253-262
89. Popp, B. V. and Ball, Z. T. (2010) Structure-selective modification of aromatic side chains with dirhodium metallopeptide catalysts J. Am. Chem. Soc. 132, 6660-6662
90. Antos, J. M., McFarland, J. M., Iavarone, A. T., and Francis, M. B. (2009) Chemoselective tryptophan labeling with rhodium carbenoids at mild pH J. Am. Chem. Soc. 131, 6301-6308
91. van Dongen, S. F. M., Teeuwen, R. L. M., Nallani, M., van Berkel, S. S., Cornelissen, J. J. L. M., Nolte, R. J. M., and van Hest, J. C. M. (2009) Single-step azide introduction in proteins via an aqueous diazo transfer Bioconjugate Chem. 20, 20-23
92. Chen, I., Howarth, M., Lin, W., and Ting, A. Y. (2005) Site-specific labeling of cell surface proteins with biophysical probes using biotin ligase Nat. Methods 2, 99-104
93. Fernandez-Suarez, M., Baruah, H., Martinez-Hernandez, L., Xie, K. T., Baskin, J. M., Bertozzi, C. R., and Ting, A. Y. (2007) Redirecting lipoic acid ligase for cell surface protein labeling with small-molecule probes Nat. Biotechnol. 25, 1483-1487
94. Carrico, I. S., Carlson, B. L., and Bertozzi, C. R. (2007) Introducing genetically encoded aldehydes into proteins Nat. Chem. Biol. 3, 321-322
95. Popp, M. W. and Ploegh, H. L. (2011) Making and breaking peptide bonds: protein engineering using sortase Angew. Chem., Int. Ed. 50, 5024-5032
96. Los, G. V., Encell, L. P., McDougall, M. G., Hartzell, D. D., Karassina, N., Zimprich, C., Wood, M. G., Learish, R., Ohana, R. F., Urh, M., Simpson, D., Mendez, J., Zimmerman, K., Otto, P., Vidugiris, G., Zhu, J., Darzins, A., Klaubert, D. H., Bulleit, R. F., and Wood, K. V. (2008) HaloTag: A novel protein labeling technology for cell imaging and protein analysis ACS Chem. Biol. 3, 373-382
97. Wu, P., Shui, W., Carlson, B. L., Hu, N., Rabuka, D., Lee, J., and Bertozzi, C. R. (2009) Site-specific chemical modification of recombinant proteins produced in mammalian cells by using the genetically encoded aldehyde tag Proc. Natl. Acad. Sci. U.S.A. 106, 3000-3005
98. Rashidian, M., Kumarapperuma, S. C., Gabrielse, K., Fegan, A., Wagner, C. R., and Distefano, M. D. (2013) Simultaneous dual protein labeling using a triorthogonal reagent J. Am. Chem. Soc. 135, 16388-16396
99. Puthenveetil, S., Liu, D. S., White, K. A., Thompson, S., and Ting, A. Y. (2009) Yeast display evolution of a kinetically efficient 13-amino acid substrate for lipoic acid ligase J. Am. Chem. Soc. 131, 16430-16438
100. Uttamapinant, C., Sanchez, M. I., Liu, D. S., Yao, J. Z., and Ting, A. Y. (2013) Site-specific protein labeling using PRIME and chelation-assisted click chemistry Nat. Protoc. 8, 1620-1634
101. Liu, D. S., Tangpeerachaikul, A., Selvaraj, R., Taylor, M. T., Fox, J. M., and Ting, A. Y. (2012) Diels-Alder cycloaddition for fluorophore targeting to specific proteins inside living cells J. Am. Chem. Soc. 134, 792-795
102. Cohen, J. D., Zou, P., and Ting, A. Y. (2012) Site-specific protein modification using lipoic acid ligase and bis-aryl hydrazone formation ChemBioChem 13, 888-894
103. Davis, L. and Chin, J. W. (2012) Designer proteins: applications of genetic code expansion in cell biology Nat. Rev. Mol. Cell Biol. 13, 168-182
104. Liu, C. C. and Schultz, P. G. (2010) Adding new chemistries to the genetic code Annu. Rev. Biochem. 79, 413-444
105. Zhang, Z., Smith, B. A., Wang, L., Brock, A., Cho, C., and Schultz, P. G. (2003) A new strategy for the site-specific modification of proteins in vivo Biochemistry 42, 6735-6746
106. Deiters, A., Cropp, T. A., Mukherji, M., Chin, J. W., Anderson, J. C., and Schultz, P. G. (2003) Adding amino acids with novel reactivity to the genetic code of Saccharomyces cerevisiae J. Am. Chem. Soc. 125, 11782-11783
107. Lee, Y. J., Wu, B., Raymond, J. E., Zeng, Y., Fang, X., Wooley, K. L., and Liu, W. R. (2013) A genetically encoded acrylamide functionality ACS Chem. Biol. 8, 1664-1670
108. Seitchik, J. L., Peeler, J. C., Taylor, M. T., Blackman, M. L., Rhoads, T. W., Cooley, R. B., Refakis, C., Fox, J. M., and Mehl, R. A. (2012) Genetically encoded tetrazine amino acid directs rapid site-specific in vivo bioorthogonal ligation with trans -cyclooctenes J. Am. Chem. Soc. 134, 2898-2901
109. Plass, T., Milles, S., Koehler, C., Szymanski, J., Mueller, R., Wiessler, M., Schultz, C., and Lemke, E. A. (2012) Amino acids for Diels-Alder reactions in living cells Angew. Chem., Int. Ed. 51, 4166-4170
110. Lang, K., Davis, L., Wallace, S., Mahesh, M., Cox, D. J., Blackman, M. L., Fox, J. M., and Chin, J. W. (2012) Genetic encoding of bicyclononynes and trans-cyclooctenes for site-specific protein labeling in vitro and in live mammalian cells via rapid fluorogenic Diels-Alder reactions J. Am. Chem. Soc. 134, 10317-10320
111. Lang, K., Davis, L., Torres-Kolbus, J., Chou, C., Deiters, A., and Chin, J. W. (2012) Genetically encoded norbornene directs site-specific cellular protein labelling via a rapid bioorthogonal reaction Nat. Chem. 4, 298-304
112. Li, F., Zhang, H., Sun, Y., Pan, Y., Zhou, J., and Wang, J. (2013) Expanding the genetic code for photoclick chemistry in E. coli, mammalian cells, and A. thaliana Angew. Chem., Int. Ed. 52, 9700-9704
113. Bianco, A., Townsley, F. M., Greiss, S., Lang, K., and Chin, J. W. (2012) Expanding the genetic code of Drosophila melanogaster Nat. Chem. Biol. 8, 748-750
114. Neumann, H., Wang, K., Davis, L., Garcia-Alai, M., and Chin, J. W. (2010) Encoding multiple unnatural amino acids via evolution of a quadruplet-decoding ribosome Nature 464, 441-444
115. Wan, W., Huang, Y., Wang, Z., Russell, W. K., Pai, P. J., Russell, D. H., and Liu, W. R. (2010) A facile system for genetic incorporation of two different noncanonical amino acids into one protein in Escherichia coli Angew. Chem., Int. Ed. 49, 3211-3214
116. Dieterich, D. C., Link, A. J., Graumann, J., Tirrell, D. A., and Schuman, E. M. (2006) Selective identification of newly synthesized proteins in mammalian cells using bioorthogonal noncanonical amino acid tagging (BONCAT) Proc. Natl. Acad. Sci. U.S.A. 103, 9482-9487
117. Ngo, J. T. and Tirrell, D. A. (2011) Noncanonical amino acids in the interrogation of cellular protein synthesis Acc. Chem. Res. 44, 677-685
118. Geoghegan, K. F. and Stroh, J. G. (1992) Site-directed conjugation of nonpeptide groups to peptides and proteins via periodate oxidation of a 2-amino alcohol. Application to modification at N-terminal serine Bioconjugate Chem. 3, 138-146
119. Clark, P. M., Dweck, J. F., Mason, D. E., Hart, C. R., Buck, S. B., Peters, E. C., Agnew, B. J., and Hsieh-Wilson, L. C. (2008) Direct in-gel fluorescence detection and cellular imaging of O-GlcNAc-modified proteins J. Am. Chem. Soc. 130, 11576-11577
120. Soriano Del Amo, D., Wang, W., Jiang, H., Besanceney, C., Yan, A. C., Levy, M., Liu, Y., Marlow, F. L., and Wu, P. (2010) Biocompatible copper(I) catalysts for in vivo imaging of glycans J. Am. Chem. Soc. 132, 16893-16899
121. Besanceney-Webler, C., Jiang, H., Zheng, T., Feng, L., Soriano del Amo, D., Wang, W., Klivansky, L. M., Marlow, F. L., Liu, Y., and Wu, P. (2011) Increasing the efficacy of bioorthogonal click reactions for bioconjugation: A comparative study Angew. Chem., Int. Ed. 50, 8051-8056
122. Hong, V., Presolski, S. I., Ma, C., and Finn, M. G. (2009) Analysis and optimization of copper-catalyzed azide-alkyne cycloaddition for bioconjugation Angew. Chem., Int. Ed. 48, 9879-9883
123. Hong, V., Steinmetz, N. F., Manchester, M., and Finn, M. G. (2010) Labeling live cells by copper-catalyzed alkyne-azide click chemistry Bioconjugate Chem. 21, 1912-1916
124. Kennedy, D. C., McKay, C. S., Legault, M. C., Danielson, D. C., Blake, J. A., Pegoraro, A. F., Stolow, A., Mester, Z., and Pezacki, J. P. (2011) Cellular consequences of copper complexes used to catalyze bioorthogonal click reactions J. Am. Chem. Soc. 133, 17993-18001
125. Uttamapinant, C., Tangpeerachaikul, A., Grecian, S., Clarke, S., Singh, U., Slade, P., Gee, K. R., and Ting, A. Y. (2012) Fast, cell-compatible click chemistry with copper-chelating azides for biomolecular labeling Angew. Chem., Int. Ed. 51, 5852-5856
126. Brotherton, W. S., Michaels, H. A., Simmons, J. T., Clark, R. J., Dalal, N. S., and Zhu, L. (2009) Apparent copper(II)-accelerated azide-alkyne cycloaddition Org. Lett. 11, 4954-4957
127. Kuang, G. C., Guha, P. M., Brotherton, W. S., Simmons, J. T., Stankee, L. A., Nguyen, B. T., Clark, R. J., and Zhu, L. (2011) Experimental investigation on the mechanism of chelation-assisted, copper(II) acetate-accelerated azide-alkyne cycloaddition J. Am. Chem. Soc. 133, 13984-14001
128. Yao, J. Z., Uttamapinant, C., Poloukhtine, A., Baskin, J. M., Codelli, J. A., Sletten, E. M., Bertozzi, C. R., Popik, V. V., and Ting, A. Y. (2012) Fluorophore targeting to cellular proteins via enzyme-mediated azide ligation and strain-promoted cycloaddition J. Am. Chem. Soc. 134, 3720-3728
129. Kim, E. J., Kang, D. W., Leucke, H. F., Bond, M. R., Ghosh, S., Love, D. C., Ahn, J. S., Kang, D. O., and Hanover, J. A. (2013) Optimizing the selectivity of DIFO-based reagents for intracellular bioorthogonal applications Carbohydr. Res. 377, 18-27
130. Mackinnon, A. L. and Taunton, J. (2009) Target Identification by diazirine photo-cross-linking and click chemistry Curr. Protoc. Chem. Biol. 1, 55-73
131. Speers, A. E. and Cravatt, B. F. (2004) Profiling enzyme activities in vivo using click chemistry methods Chem. Biol. 11, 535-546
132. Boyce, M., Carrico, I. S., Ganguli, A. S., Yu, S. H., Hangauer, M. J., Hubbard, S. C., Kohler, J. J., and Bertozzi, C. R. (2011) Metabolic cross-talk allows labeling of O-linked β -N -acetylglucosamine-modified proteins via the N -acetylgalactosamine salvage pathway Proc. Natl. Acad. Sci. U.S.A. 108, 3141-3146
133. Agard, N. J., Baskin, J. M., Prescher, J. A., Lo, A., and Bertozzi, C. R. (2006) A comparative study of bioorthogonal reactions with azides ACS Chem. Biol. 1, 644-648
134. Grammel, M. and Hang, H. C. (2013) Chemical reporters for biological discovery Nat. Chem. Biol. 9, 475-484
135. Ekkebus, R., van Kasteren, S. I., Kulathu, Y., Scholten, A., Berlin, I., Geurink, P. P., de Jong, A., Goerdayal, S., Neefjes, J., Heck, A. J., Komander, D., and Ovaa, H. (2013) On terminal alkynes that can react with active-site cysteine nucleophiles in proteases J. Am. Chem. Soc. 135, 2867-2870
136. Dieterich, D. C., Hodas, J. J., Gouzer, G., Shadrin, I. Y., Ngo, J. T., Triller, A., Tirrell, D. A., and Schuman, E. M. (2010) In situ visualization and dynamics of newly synthesized proteins in rat hippocampal neurons Nat. Neurosci. 13, 897-905
137. Agard, N. J. and Bertozzi, C. R. (2009) Chemical approaches to perturb, profile, and perceive glycans Acc. Chem. Res. 42, 788-797
138. 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
139. Mbua, N. E., Flanagan-Steet, H., Johnson, S., Wolfert, M. A., Boons, G. J., and Steet, R. (2013) Abnormal accumulation and recycling of glycoproteins visualized in Niemann-Pick type C cells using the chemical reporter strategy Proc. Natl. Acad. Sci. U.S.A. 110, 10207-10212
140. Hang, H. C., Wilson, J. P., and Charron, G. (2011) Bioorthogonal chemical reporters for analyzing protein lipidation and lipid trafficking Acc. Chem. Res. 44, 699-708
141. Kostiuk, M. A., Corvi, M. M., Keller, B. O., Plummer, G., Prescher, J. A., Hangauer, M. J., Bertozzi, C. R., Rajaiah, G., Falck, J. R., and Berthiaume, L. G. (2008) Identification of palmitoylated mitochondrial proteins using a bio-orthogonal azido-palmitate analogue FASEB J. 22, 721-732
142. Heal, W. P., Jovanovic, B., Bessin, S., Wright, M. H., Magee, A. I., and Tate, E. W. (2011) Bioorthogonal chemical tagging of protein cholesterylation in living cells Chem. Commun. 47, 4081-4083
143. Hsu, T. L., Hanson, S. R., Kishikawa, K., Wang, S. K., Sawa, M., and Wong, C. H. (2007) Alkynyl sugar analogs for the labeling and visualization of glycoconjugates in cells Proc. Natl. Acad. Sci. U.S.A. 104, 2614-2619
144. Huang, H. W., Chen, C. H., Lin, C. H., Wong, C. H., and Lin, K. I. (2013) B-cell maturation antigen is modified by a single N-glycan chain that modulates ligand binding and surface retention Proc. Natl. Acad. Sci. U.S.A. 110, 10928-10933
145. Anderson, C. T., Wallace, I. S., and Somerville, C. R. (2012) Metabolic click-labeling with a fucose analog reveals pectin delivery, architecture, and dynamics in Arabidopsis cell walls Proc. Natl. Acad. Sci. U.S.A. 109, 1329-1334
146. Liu, Y. C., Yen, H. Y., Chen, C. Y., Chen, C. H., Cheng, P. F., Juan, Y. H., Khoo, K. H., Yu, C. J., Yang, P. C., Hsu, T. L., and Wong, C. H. (2011) Sialylation and fucosylation of epidermal growth factor receptor suppress its dimerization and activation in lung cancer cells Proc. Natl. Acad. Sci. U.S.A. 108, 11332-11337
147. Charron, G., Li, M. M., MacDonald, M. R., and Hang, H. C. (2013) Prenylome profiling reveals S-farnesylation is crucial for membrane targeting and antiviral activity of ZAP long-isoform Proc. Natl. Acad. Sci. U.S.A. 110, 11085-11090
148. Martin, B. R., Wang, C., Adibekian, A., Tully, S. E., and Cravatt, B. F. (2012) Global profiling of dynamic protein palmitoylation Nat. Methods 9, 84-89
149. Niederwieser, A., Spate, A. K., Nguyen, L. D., Jungst, C., Reutter, W., and Wittmann, V. (2013) Two-color glycan labeling of live cells by a combination of Diels-Alder and click chemistry Angew. Chem., Int. Ed. 52, 4265-4268
150. Stockmann, H., Neves, A. A., Stairs, S., Brindle, K. M., and Leeper, F. J. (2011) Exploring isonitrile-based click chemistry for ligation with biomolecules Org. Biomol. Chem. 9, 7303-7305
151. Wainman, Y. A., Neves, A. A., Stairs, S., Stockmann, H., Ireland-Zecchini, H., Brindle, K. M., and Leeper, F. J. (2013) Dual-sugar imaging using isonitrile and azido-based click chemistries Org. Biomol. Chem. 11, 7297-7300
152. Stairs, S., Neves, A. A., Stockmann, H., Wainman, Y. A., Ireland-Zecchini, H., Brindle, K. M., and Leeper, F. J. (2013) Metabolic glycan imaging by isonitrile-tetrazine click chemistry ChemBioChem 14, 1063-1067
153. Han, M. J., Xiong, D. C., and Ye, X. S. (2012) Enabling Wittig reaction on site-specific protein modification Chem. Commun. 48, 11079-11081
154. Lum, K. M., Xavier, V. J., Ong, M. J., Johannes, C. W., and Chan, K. P. (2013) Stabilized Wittig olefination for bioconjugation Chem. Commun. 49, 11188-11190
155. Rossin, R., Lappchen, T., van den Bosch, S. M., Laforest, R., and Robillard, M. S. (2013) Diels-Alder reaction for tumor pretargeting: In vivo chemistry can boost tumor radiation dose compared with directly labeled antibody J. Nucl. Med. 54, 1989-1995
156. Vugts, D. J., Vervoort, A., Stigter-van Walsum, M., Visser, G. W., Robillard, M. S., Versteegen, R. M., Vulders, R. C., Herscheid, J. K., and van Dongen, G. A. (2011) Synthesis of phosphine and antibody-azide probes for in vivo Staudinger ligation in a pretargeted imaging and therapy approach Bioconjugate Chem. 22, 2072-2081
157. Hausner, S. H., Carpenter, R. D., Bauer, N., and Sutcliffe, J. L. (2013) Evaluation of an integrin αvβ6-specific peptide labeled with [18F]fluorine by copper-free, strain-promoted click chemistry Nucl. Med. Biol. 40, 233-239
158. Bouvet, V., Wuest, M., and Wuest, F. (2011) Copper-free click chemistry with the short-lived positron emitter fluorine-18 Org. Biomol. Chem. 9, 7393-7399
159. Carlson, J. C. T., Meimetis, L. G., Hilderbrand, S. A., and Weissleder, R. (2013) BODIPY-tetrazine derivatives as superbright bioorthogonal turn-on probes Angew. Chem., Int. Ed. 52, 6917-6920
160. Friscourt, F., Fahrni, C. J., and Boons, G. J. (2012) A fluorogenic probe for the catalyst-free detection of azide-tagged molecules J. Am. Chem. Soc. 134, 18809-18815
161. Jewett, J. C. and Bertozzi, C. R. (2011) Synthesis of a fluorogenic cyclooctyne activated by Cu-free click chemistry Org. Lett. 13, 5937-5939
162. Devaraj, N. K., Hilderbrand, S., Upadhyay, R., Mazitschek, R., and Weissleder, R. (2010) Bioorthogonal turn-on probes for imaging small molecules inside living cells Angew. Chem., Int. Ed. 49, 2869-2872
163. Shieh, P., Hangauer, M. J., and Bertozzi, C. R. (2012) Fluorogenic azidofluoresceins for biological imaging J. Am. Chem. Soc. 134, 17428-17431
164. Herner, A., Nikic, I., Kallay, M., Lemke, E. A., and Kele, P. (2013) A new family of bioorthogonally applicable fluorogenic labels Org. Biomol. Chem. 11, 3297-3306
165. Yang, J., Karver, M. R., Li, W., Sahu, S., and Devaraj, N. K. (2012) Metal-catalyzed one-pot synthesis of tetrazines directly from aliphatic nitriles and hydrazine Angew. Chem., Int. Ed. 51, 5222-5225
166. Yao, J. Z., Uttamapinant, C., Poloukhtine, A., Baskin, J. M., Codelli, J. A., Sletten, E. M., Bertozzi, C. R., Popik, V. V., and Ting, A. Y. (2012) Fluorophore targeting to cellular proteins via enzyme-mediated azide ligation and strain-promoted cycloaddition J. Am. Chem. Soc. 134, 3720-3728
167. Lin, F. L., Hoyt, H. M., van Halbeek, H., Bergman, R. G., and Bertozzi, C. R. (2005) Mechanistic investigation of the Staudinger ligation J. Am. Chem. Soc. 127, 2686-2695
168. Majkut, P., Bohrsch, V., Serwa, R., Gerrits, M., and Hackenberger, C. P. (2012) Site-specific modification of proteins by the Staudinger-phosphite reaction Methods Mol. Biol. 794, 241-249
169. Hangauer, M. J. and Bertozzi, C. R. (2008) A FRET-based fluorogenic phosphine for live-cell imaging with the Staudinger ligation Angew. Chem., Int. Ed. 47, 2394-2397
170. Saxon, E., Armstrong, J. I., and Bertozzi, C. R. (2000) A 'traceless' Staudinger ligation for the chemoselective synthesis of amide bonds Org. Lett. 2, 2141-2143
171. Soellner, M. B., Tam, A., and Raines, R. T. (2006) Staudinger ligation of peptides at non-glycyl residues J. Org. Chem. 71, 9824-9830
172. Tam, A. and Raines, R. T. (2009) Protein engineering with the traceless Staudinger ligation Method Enzymol. 462, 25-44
173. Ahad, A. M., Jensen, S. M., and Jewett, J. C. (2013) A traceless Staudinger reagent to deliver diazirines Org. Lett. 15, 5060-5063
174. Bertran-Vicente, J. and Hackenberger, C. P. (2013) A supramolecular
175. DeForest, C. A. and Anseth, K. S. (2011) Cytocompatible click-based hydrogels with dynamically tunable properties through orthogonal photoconjugation and photocleavage reactions Nat. Chem. 3, 925-931
176. Kafri, R., Levy, J., Ginzberg, M. B., Oh, S., Lahav, G., and Kirschner, M. W. (2013) Dynamics extracted from fixed cells reveal feedback linking cell growth to cell cycle Nature 494, 480-483
177. Chakraborty, A., Wang, D., Ebright, Y. W., Korlann, Y., Kortkhonjia, E., Kim, T., Chowdhury, S., Wigneshweraraj, S., Irschik, H., Jansen, R., Nixon, B. T., Knight, J., Weiss, S., and Ebright, R. H. (2012) Opening and closing of the bacterial RNA polymerase clamp Science 337, 591-595
178. Liang, G., Ren, H., and Rao, J. (2010) A biocompatible condensation reaction for controlled assembly of nanostructures in living cells Nat. Chem. 2, 54-60
179. Nguyen, D. P., Elliott, T., Holt, M., Muir, T. W., and Chin, J. W. (2011) Genetically encoded 1,2-aminothiols facilitate rapid and site-specific protein labeling via a bio-orthogonal cyanobenzothiazole condensation J. Am. Chem. Soc. 133, 11418-11421
180. Lin, Y. A., Boutureira, O., Lercher, L., Bhushan, B., Paton, R. S., and Davis, B. G. (2013) Rapid cross-metathesis for reversible protein modifications via chemical access to Se-allyl-selenocysteine in proteins J. Am. Chem. Soc. 135, 12156-12159
181. Sletten, E. M. and Bertozzi, C. R. (2011) A bioorthogonal quadricyclane ligation J. Am. Chem. Soc. 133, 17570-17573
182. Ho, C. M., Zhang, J. L., Zhou, C. Y., Chan, O. Y., Yan, J. J., Zhang, F. Y., Huang, J. S., and Che, C. M. (2010) A water-soluble ruthenium glycosylated porphyrin catalyst for carbenoid transfer reactions in aqueous media with applications in bioconjugation reactions J. Am. Chem. Soc. 132, 1886-1894
183. Lin, Y. A., Chalker, J. M., and Davis, B. G. (2010) Olefin cross-metathesis on proteins: investigation of allylic chalcogen effects and guiding principles in metathesis partner selection J. Am. Chem. Soc. 132, 16805-16811
184. Chalker, J. M., Wood, C. S., and Davis, B. G. (2009) A convenient catalyst for aqueous and protein Suzuki-Miyaura cross-coupling J. Am. Chem. Soc. 131, 16346-16347
185. Li, N., Lim, R. K., Edwardraja, S., and Lin, Q. (2011) Copper-free Sonogashira cross-coupling for functionalization of alkyne-encoded proteins in aqueous medium and in bacterial cells J. Am. Chem. Soc. 133, 15316-15319
186. Yusop, R. M., Unciti-Broceta, A., Johansson, E. M., Sanchez-Martin, R. M., and Bradley, M. (2011) Palladium-mediated intracellular chemistry Nat. Chem. 3, 239-243
187. Spicer, C. D., Triemer, T., and Davis, B. G. (2012) Palladium-mediated cell-surface labeling J. Am. Chem. Soc. 134, 800-803
188. Lercher, L., McGouran, J. F., Kessler, B. M., Schofield, C. J., and Davis, B. G. (2013) DNA modification under mild conditions by Suzuki-Miyaura cross-coupling for the generation of functional probes Angew. Chem., Int. Ed. 52, 10553-10558
189. Li, J., Lin, S., Wang, J., Jia, S., Yang, M., Hao, Z., Zhang, X., and Chen, P. R. (2013) Ligand-free palladium-mediated site-specific protein labeling inside gram-negative bacterial pathogens J. Am. Chem. Soc. 135, 7330-7338
190. Riggsbee, C. W. and Deiters, A. (2010) Recent advances in the photochemical control of protein function Trends Biotechnol. 28, 468-475
191. Pauloehrl, T., Delaittre, G., Winkler, V., Welle, A., Bruns, M., Borner, H. G., Greiner, A. M., Bastmeyer, M., and Barner-Kowollik, C. (2012) Adding spatial control to click chemistry: phototriggered Diels-Alder surface (bio)functionalization at ambient temperature Angew. Chem., Int. Ed. 51, 1071-1074
192. Arumugam, S. and Popik, V. V. (2011) Light-induced hetero-Diels-Alder cycloaddition: A facile and selective photoclick reaction J. Am. Chem. Soc. 133, 5573-5579
193. Adzima, B. J., Tao, Y. H., Kloxin, C. J., DeForest, C. A., Anseth, K. S., and Bowman, C. N. (2011) Spatial and temporal control of the alkyne-azide cycloaddition by photoinitiated Cu(II) reduction Nat. Chem. 3, 256-259
194. Wang, Y., Song, W., Hu, W. J., and Lin, Q. (2009) Fast alkene functionalization in vivo by Photoclick chemistry: HOMO lifting of nitrile imine dipoles Angew. Chem., Int. Ed. 48, 5330-5333
195. Poloukhtine, A. A., Mbua, N. E., Wolfert, M. A., Boons, G. J., and Popik, V. V. (2009) Selective labeling of living cells by a photo-triggered click reaction J. Am. Chem. Soc. 131, 15769-15776
196. Deiters, A. (2010) Principles and applications of the photochemical control of cellular processes ChemBioChem 11, 47-53
197. Lim, R. K. and Lin, Q. (2011) Photoinducible bioorthogonal chemistry: A spatiotemporally controllable tool to visualize and perturb proteins in live cells Acc. Chem. Res. 44, 828-839
198. McNitt, C. D. and Popik, V. V. (2012) Photochemical generation of oxa-dibenzocyclooctyne (ODIBO) for metal-free click ligations Org. Biomol. Chem. 10, 8200-8202
199. Yu, Z., Ohulchanskyy, T. Y., An, P., Prasad, P. N., and Lin, Q. (2013) Fluorogenic, two-photon triggered photoclick chemistry in live mammalian cells J. Am. Chem. Soc. 135, 16766-16769
200. Li, Q., Dong, T., Liu, X., and Lei, X. (2013) A bioorthogonal ligation enabled by click cycloaddition of o -quinolinone quinone methide and vinyl thioether J. Am. Chem. Soc. 135, 4996-4999
201. An, P., Yu, Z. P., and Lin, Q. (2013) Design of oligothiophene-based tetrazoles for laser-triggered photoclick chemistry in living cells Chem. Commun. 49, 9920-9922
202. Chen, W. X., Wang, D. Z., Dai, C. F., Hamelberg, D., and Wang, B. H. (2012) Clicking 1,2,4,5-tetrazine and cyclooctynes with tunable reaction rates Chem. Commun. 48, 1736-1738
203. Liang, Y., Mackey, J. L., Lopez, S. A., Liu, F., and Houk, K. N. (2012) Control and design of mutual orthogonality in bioorthogonal cycloadditions J. Am. Chem. Soc. 134, 17904-17907
204. Karver, M. R., Weissleder, R., and Hilderbrand, S. A. (2012) Bioorthogonal reaction pairs enable simultaneous, selective, multi-target imaging Angew. Chem., Int. Ed. 51, 920-922
205. Willems, L. I., Li, N., Florea, B. I., Ruben, M., van der Marel, G. A., and Overkleeft, H. S. (2012) Triple bioorthogonal ligation strategy for simultaneous labeling of multiple enzymatic activities Angew. Chem., Int. Ed. 51, 4431-4434
206. 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
207. Schoenebeck, F., Ess, D. H., Jones, G. O., and Houk, K. N. (2009) Reactivity and regioselectivity in 1,3-dipolar cycloadditions of azides to strained alkynes and alkenes: A computational study J. Am. Chem. Soc. 131, 8121-8133
208. Kamber, D. N., Nazarova, L. A., Liang, Y., Lopez, S. A., Patterson, D. M., Shih, H. W., Houk, K. N., and Prescher, J. A. (2013) Isomeric cyclopropenes exhibit unique bioorthogonal reactivities J. Am. Chem. Soc. 135, 13680-13683
209. Gold, B., Dudley, G. B., and Alabugin, I. V. (2013) Moderating strain without sacrificing reactivity: Design of fast and tunable noncatalyzed alkyne-azide cycloadditions via stereoelectronically controlled transition state stabilization J. Am. Chem. Soc. 135, 1558-1569
210. Kolodych, S., Rasolofonjatovo, E., Chaumontet, M., Nevers, M. C., Creminon, C., and Taran, F. (2013) Discovery of chemoselective and biocompatible reactions using a high-throughput immunoassay screening Angew. Chem., Int. Ed. 52, 12056-12060