Bioconjugation with strained alkenes and alkynes

Accounts of Chemical Research

Volumn 44, Issue 9, 2011, Pages 805-815

  Debets, Marjoke F ^a   Van Berkel, Sander S ^a   Dommerholt, Jan ^a   Dirks, A J ^a   Rutjes, Floris P J T ^a   Van Delft, Floris L ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKYNE; AZIDE; COPPER; NUCLEIC ACID; PROTEIN;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION;

ALKENES; ALKYNES; AZIDES; CATALYSIS; COPPER; CYCLIZATION; NUCLEIC ACIDS; PROTEINS;

EID: 80053007626     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar200059z     Document Type: Article

References (86)

1. e-EROS Encyclopedia of Reagents for Organic Synthesis; John Wiley & Sons, Ltd: 2010.
2. Saxon, E.; Bertozzi, C. R. Cell Surface Engineering by a Modified Staudinger Reaction Science 2000, 287, 2007-2010 (Pubitemid 30158675)
3. Köhn, M.; Breinbauer, R. The Staudinger Ligation-A Gift to Chemical Biology Angew. Chem., Int. Ed. 2004, 43, 3106-3116 (Pubitemid 39257599)
4. van Berkel, S. S.; van Eldijk, M.; van Hest, J. C. M. Staudinger Ligation as Tool for Bioconjugation. Angew. Chem., Int. Ed. 2011, DOI: 10.1002/anie.201008102.
5. Huisgen, R. 1,3-Dipolar Cycloadditions-Introduction, Survey, Mechanism. In 1,3-dipolar cycloaddition chemistry; Padwa, A., Ed.; John Wiley & Sons Inc.: New York, 1984; Vol. 1.
6. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Click Chemistry: Diverse Chemical Function from a Few Good Reactions Angew. Chem., Int. Ed. 2002, 41, 2596-2599
7. Alder, K.; Stein, G. Über das Abgestufte Additionsvermögen von Ungesättigten Ringsystemen Liebigs Ann. Chem. 1931, 485, 211-222
8. Alder, K.; Stein, G. Über das Abgestufte Additionsvermögen von Ungesättigten Ringsystemen II Liebigs Ann. Chem. 1933, 501, 1-48
9. Huisgen, R.; Ooms, P. H. J.; Mingin, M.; Allinger, N. L. Exceptional Reactivity of the Bicyclo[2.2.1]heptene Double Bond J. Am. Chem. Soc. 1980, 102, 3951-3953
10. Huisgen, R. Cycloadditions-Definition, Classification, and Characterization Angew. Chem., Int. Ed. 1968, 7, 321-328
11. Li, Z.; Seo, T. S.; Ju, J. 1,3-Dipolar Cycloaddition of Azides with Electron-deficient Alkynes under mild Conditions in Water Tetrahedron Lett. 2004, 45, 3143-3146 (Pubitemid 38373748)
12. Reinhoudt, D. N.; Kouwenhoven, C. G. Retro-Diels-Alder Reactions of Heterocyclic Compounds under mild Conditions Tetrahedron Lett. 1974, 25, 2163-2166
13. 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. Metal-Free Triazole Formation as a Tool for Bioconjugation ChemBioChem 2007, 8, 1504-1508 (Pubitemid 47436906)
14. Gutsmiedl, K.; Wirges, C. T.; Ehmke, V.; Carell, T. Copper-Free "Click" Modification of DNA via Nitrile Oxide-Norbornene 1,3-Dipolar Cycloaddition Org. Lett. 2009, 11, 2405-2408
15. Devaraj, N. K.; Weissleder, R.; Hilderbrand, S. A. Tetrazine-Based Cycloadditions: Application to Pretargeted Live Cell Imaging Bioconjugate Chem. 2008, 19, 2297-2299
16. Thalhammer, F.; Wallfahrer, U.; Sauer, J. Reactivity of Simple Open-chain and Cyclic Dienophiles in inverse Electron-demand Diels-Alder Reactions Tetrahedron Lett. 1990, 47, 6851-6854 (Pubitemid 20358445)
17. Pipkorn, R.; Waldeck, W.; Didinger, B.; Koch, M.; Mueller, G.; Wiessler, M.; Braun, K. Inverse-electron-demand Diels-Alder reaction as a highly Efficient Chemoselective Ligation Procedure: Synthesis and Function of a BioShuttle for Temozolomide Transport into Prostate Cancer Cells J. Pept. Sci. 2009, 15, 235-241
18. Royzen, M.; Yap, G. P. A.; Fox, J. M. A Photochemical Synthesis of Functionalized trans-Cyclooctenes Driven by Metal Complexation J. Am. Chem. Soc. 2008, 130, 3760-3761 (Pubitemid 351429835)
19. Greenberg, A.; Liebman, J. F. Strained Organic Molecules; Academic Press: New York, 1982.
20. Shea, K. J.; Kim, J.-S. Influence of Strain on Chemical Reactivity. Relative Reactivity of Torsionally Strained Double Bonds in 1,3-Dipolar Cycloadditions J. Am. Chem. Soc. 1992, 114, 4846-4855
21. Blackman, M. L.; Royzen, M.; Fox, J. M. Tetrazine Ligation: Fast Bioconjugation Based on Inverse-Electron-Demand Diels-Alder Reactivity J. Am. Chem. Soc. 2008, 130, 13518-13519
22. Rossin, R.; Verkerk, P. R.; van den Bosch, S. M.; Vulders, R. C. M.; Verel, I.; Lub, J.; Robillard, M. S. In Vivo Chemistry for Pretargeted Tumor Imaging in Live Mice Angew. Chem., Int. Ed. 2010, 49, 3375-3378
23. Rickborn, B. The Retro-Diels-Alder Reaction. Part I. C-C Dienophiles, Org. React. 1998, 52, 1-393.
24. Rickborn, B. The Retro-Diels-Alder Reaction. Part II. Dienophiles with One or More Heteroatoms Org. React. 1998, 53, 223-629
25. Sivakumar, K.; Xie, F.; Cash, B. M.; Long, S.; Barnhill, H. N.; Wang, Q. A Fluorogenic 1,3-Dipolar Cycloaddition Reaction of 3-Azidocoumarins and Acetylenes Org. Lett. 2004, 6, 4603-4606 (Pubitemid 39611821)
26. van Berkel, S. S.; Dirks, A. J.; Meeuwissen, S. A.; Pingen, D. L. L.; Boerman, O. C.; Laverman, P.; van Delft, F. L.; Cornelissen, J. J. L. M.; Rutjes, F. P. J. T. Application of Metal-Free Triazole Formation in the Synthesis of Cyclic RGD-DTPA Conjugates ChemBioChem 2008, 9, 1805-1815
27. 111In]-DTPA-RGD Conjugates Nucl. Med. Biol. 2009, 36, 749-757
28. van Dongen, S. F. M.; Verdurmen, W. P. R.; Peters, R. J. R. W.; Nolte, R. J. M.; Brock, R.; van Hest, J. C. M. Cellular Integration of an Enzyme-Loaded Polymersome Nanoreactor Angew. Chem., Int. Ed. 2010, 49, 7213-7216
29. Devaraj, N. K.; Hilderbrand, S.; Upadhyay, R.; Mazitschek, R.; Weissleder, R. Bioorthogonal Turn-On Probes for Imaging Small Molecules inside Living Cells Angew. Chem., Int. Ed. 2010, 49, 2869-2872
30. 18F-labeled Probes Chem. Commun. 2010, 46, 8043-8045
31. Schoch, J.; Wiessler, M.; Jäschke, A. Post-Synthetic Modification of DNA by Inverse-Electron-Demand Diels-Alder Reaction J. Am. Chem. Soc. 2010, 132, 8846-8847
32. Han, H.-S.; Devaraj, N. K.; Lee, J.; Hilderbrand, S. A.; Weissleder, R.; Bawendi, M. G. Development of a Bioorthogonal and Highly Efficient Conjugation Method for Quantum Dots Using Tetrazine-Norbornene Cycloaddition J. Am. Chem. Soc. 2010, 132, 7838-7839
33. Huisgen, R.; Gambra, F. P. 1,3-Dipolar Cycloadditions of Aromatic Azoxy Compounds to Strained Cycloalkenes Tetrahedron Lett. 1982, 23, 55-58
34. Krebs, A.; Wilke, J. Angle-strained Alkynes Top. Curr. Chem. 1983, 109, 189-233
35. Heber, D.; Rösner, P.; Tochtermann, W. Cyclooctyne and 4-Cyclooctyn-1-ol - Versatile Building Blocks in Organic Synthesis Eur. J. Org. Chem. 2005, 4231-4247 (Pubitemid 41502521)
36. Blomquist, A. T.; Liu, L. H. Many-membered Carbon Rings. VII. Cyclooctyne J. Am. Chem. Soc. 1953, 75, 2153-2154
37. Wittig, G.; Krebs, A. On the Existence of Small-membered Cycloalkynes, I Chem. Ber. 1961, 94, 3260-3275
38. Agard, N. J.; Prescher, J. A.; Bertozzi, C. R. A Strain-Promoted [3 + 2] Azide-Alkyne Cycloaddition for Covalent Modification of Biomolecules in Living Systems J. Am. Chem. Soc. 2004, 126, 15046-15047 (Pubitemid 39557262)
39. Tornøe, C. W.; Christensen, C.; Meldal, M. 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. 2002, 67, 3057-3064 (Pubitemid 34457265)
40. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective "Ligation" of Azides and Terminal Alkynes Angew. Chem., Int. Ed. 2002, 41, 2596-2599 (Pubitemid 34803480)
41. Wu, P.; Fokin, V. V. Catalytic Azide-Alkyne Cycloaddition: Reactivity and Applications Aldrichimica Acta 2007, 40, 7-16
42. Meldal, M.; Tornøe, C. W. Cu-Catalyzed Azide-Alkyne Cycloaddition Chem. Rev. 2008, 108, 2952-3015
43. Del Amo, D. S.; Wang, W.; Jiang, H.; Besanceney, C.; Yan, A. C.; Levy, M.; Liu, Y.; Marlow, F. L.; Wu, P. Biocompatible Copper(I) Catalysts for in Vivo Imaging of Glycans J. Am. Chem. Soc. 2010, 132, 16893-16899
44. Agard, N. J.; Baskin, J. M.; Prescher, J. A.; Lo, A.; Bertozzi, C. R. A Comparative Study of Bioorthogonal Reactions with Azides ACS Chem. Biol. 2006, 1, 644-648
45. Baskin, J. M.; Prescher, J. A.; Laughlin, S. T.; Agard, N. J.; Chang, P. V.; Miller, I. A.; Lo, A.; Codelli, J. A.; Bertozzi, C. R. Copper-free Click chemistry for Dynamic in Vivo Imaging Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 16793-16797 (Pubitemid 350210944)
46. Codelli, J. A.; Baskin, J. M.; Agard, N. J.; Bertozzi, C. R. Second-Generation Difluorinated Cyclooctynes for Copper-Free Click Chemistry J. Am. Chem. Soc. 2008, 130, 11486-11493
47. Ning, X.; Guo, J.; Wolfert, M. A.; Boons, G.-J. Visualizing Metabolically Labeled Glycoconjugates of Living Cells by Copper-Free and Fast Huisgen Cycloadditions Angew. Chem., Int. Ed. 2008, 47, 2253-2255
48. Debets, M. F.; van Berkel, S. S.; Schoffelen, S.; Rutjes, F. P. J. T.; van Hest, J. C. M.; van Delft, F. L. Aza-dibenzocyclooctynes for fast and efficient enzyme PEGylation via copper-free (3 + 2) cycloaddition Chem. Commun. 2010, 46, 97-99
49. Kuzmin, A.; Poloukhtine, A.; Wolfert, M. A.; Popik, V. V. Surface functionalization using catalyst-free azide-alkyne cycloaddition Bioconjugate Chem. 2010, 21, 2076-2085
50. Jewett, J. C.; Sletten, E. M.; Bertozzi, C. R. Rapid Cu-Free Click Chemistry with Readily Synthesized Biarylazacyclooctynones J. Am. Chem. Soc. 2010, 132, 3688-3690
51. Antony-Meyer, C.; Meier, H. Bicyclo[6.1.0]nonyne Chem. Ber. 1988, 121, 2013-2018
52. Dommerholt, J.; Schmidt, S.; Temming, R.; Hendriks, L. J. A.; Rutjes, F. P. J. T.; van Hest, J. C. M.; Lefeber, D. J.; Friedl, P.; van Delft, F. L. Readily Accessible Bicyclononynes for Bioorthogonal Labeling and Three-Dimensional Imaging of Living Cells Angew. Chem., Int. Ed. 2010, 49, 9422-9425
53. Jewett, J. C.; Bertozzi, C. R. Chem. Soc. Rev. 2010, 39, 1272-1279
54. Baskin, J. M.; Bertozzi, C. R. Copper-Free Click Chemistry: Bioorthogonal Reagents for Tagging Azides Aldrichimica Acta 2011, 43, 15-23
55. Debets, M. F.; van der Doelen, C. W. J.; Rutjes, F. P. J. T.; van Delft, F. L. Azide: A Unique Dipole for Metal-Free Bioorthogonal Ligations ChemBioChem 2010, 11, 1168-1184
56. Chang, P. V.; Prescher, J. A.; Sletten, E. M.; Baskin, J. M.; Miller, I. A.; Agard, N. J.; Loa, A.; Bertozzi, C. R. Copper-free Click Chemistry in Living Animals Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 1821-1826
57. Sletten, E. M.; Bertozzi, C. R. A Hydrophilic Azacyclooctyne for Cu-Free Click Chemistry Org. Lett. 2008, 10, 3097-3099
58. Ning, X.; Temming, R. P.; Dommerholt, J.; Guo, J.; Ania, D. B.; Debets, M. F.; Wolfert, M. A.; Boons, G.-J.P.H.; van Delft, F. L. Protein Modification by Strain-Promoted Alkyne-Nitrone Cycloaddition Angew. Chem., Int. Ed. 2010, 49, 3065-3068
59. See also: McKay, C. S.; Moran, J.; Pezacki, J. P. Nitrones as Dipoles for Rapid Strain-Promoted 1,3-Dipolar Cycloadditions with Cyclooctynes Chem. Commun. 2010, 46, 931-933
60. Belen'kii, L. I. In Nitrile Oxides. Nitrones and Nitronates in Organic Synthesis, 2 nd ed.; Feuer, H., Ed., Wiley, Hoboken, NJ, 2008.
61. Jawalekar, A. M.; Reubsaet, E.; Rutjes, F. P. J. T.; van Delft, F. L. Synthesis of Isoxazoles by hypervalent Iodine-induced Cycloaddition of Nitrile Oxides to Alkynes Chem. Commun. 2011, 47, 3198-3200
62. Sanders, B. C.; Friscourt, F.; Ledin, P. A.; Mbua, N. A.; Arumugam, S.; Guo, J.; Boltje, T. J.; Popik, V. V.; Boons, G.-J. Metal-Free Sequential [3 + 2]-Dipolar Cycloadditions using Cyclooctynes and 1,3-Dipoles of Different Reactivity J. Am. Chem. Soc. 2011, 133, 949-957
63. Lim, R. K. V.; Lin, Q. Bioorthogonal Chemistry: Recent Progress and Future Directions Chem. Commun. 2010, 46, 1589-1600
64. Sletten, E. M.; Bertozzi, C. R. Bioorthogonal Chemistry: Fishing for Selectivity in a Sea of Functionality Angew. Chem., Int. Ed. 2009, 48, 6974-6998
65. Kiick, K. L.; Saxon, E.; Tirrell, D. A.; Bertozzi, C. R. Incorporation of Azides into Recombinant Proteins for Chemoselective Modification by the Staudinger Ligation Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 19-24 (Pubitemid 34060308)
66. Chin, J. W.; Santoro, S. W.; Martin, A. B.; King, D. S.; Wang, L.; Schultz, P. G. Addition of p -Azido- l -phenylalanine to the Genetic Code of Escherichia coli J. Am. Chem. Soc. 2002, 124, 9026-9027 (Pubitemid 34847644)
67. van Dongen, S. F. M.; Teeuwen, R. L. M.; Nallani, M.; van Berkel, S. S.; Cornelissen, J. J. L. M.; Nolte, R. J. M.; van Hest, J. C. M. Single-Step Azide introduction in Protein via an Aqueous Diazo Transfer Bioconjugate Chem. 2009, 20, 20-23
68. Geoghegan, K. F.; Stroh, J. G. 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. 1992, 3, 138-146
69. Gilmore, J. M.; Scheck, R. A.; Esser-Kahn, A. P.; Joshi, N. S.; Francis, M. B. N-terminal Protein Modification through a Biomimetic Transamination Reaction Angew. Chem., Int. Ed. 2006, 45, 5307-5311 (Pubitemid 44289366)
70. Carrico, I. S.; Carlson, B. L.; Bertozzi, C. R. Introducing Genetically Encoded Aldehydes into Proteins Nat. Chem. Biol. 2007, 3, 321-322 (Pubitemid 46789266)
71. Ebisu, K.; Tateno, H.; Kuroiwa, H.; Kawakami, K.; Ikeuchi, M.; Hirabayashi, J.; Sisido, M.; Taki, M. N-Terminal Specific Point-Immobilization of Active Proteins by the One-Pot NEXT-A Method ChemBioChem 2009, 10, 2460-2464
72. Witus, L. S.; Moore, T.; Thuronyi, B. W.; Esser-Kahn, A. P.; Scheck, R. A.; Iavarone, A. T.; Francis, M. B. Identification of Highly Reactive Sequences for PLP-Mediated Bioconjugation using a Combinatorial Peptide Library J. Am. Chem. Soc. 2010, 132, 16812-16817
73. Dawson, P. E.; Kent, S. B. H. Synthesis of Native Proteins by Chemical Ligation Annu. Rev. Biochem. 2000, 69, 923-960
74. Borgia, J. A.; Fields, G. B. Chemical Synthesis of Proteins Trends Biotechnol. 2002, 18, 243-251 (Pubitemid 30251994)
75. Kalia, J.; Raines, R. T. Hydrolytic Stability of Hydrazones and Oximes Angew. Chem., Int. Ed. 2008, 47, 7523-7526
76. Singh, I.; Heaney, F. Solid Phase Strain-Promoted "click" Modification of DNA via [3 + 2]-Nitrile Oxide-Cyclooctyne Cycloadditions Chem. Commun. 2011, 47, 2706-2708
77. Jayaprakash, K. N.; Peng, C. G.; Butler, D.; Varghese, J. P.; Maier, M. A.; Rajeev, K. G.; Manoharan, M. Non-Nucleoside Building Blocks for Copper-Assisted and Copper-Free Click Chemistry for the Efficient Synthesis of RNA Conjugates Org. Lett. 2010, 12, 5410-5413
78. van Delft, P.; Meeuwenoord, N. J.; Hoogendoorn, S.; Dinkelaar, J.; Overkleeft, H. S.; van der Marel, G. A.; Filippov, D. V. Synthesis of Oligoribonucleic Acid Conjugates Using a Cyclooctyne Phosphoramidite Org. Lett. 2010, 12, 5486-5489
79. Canalle, L. A.; van Berkel, S. S.; de Haan, L. T.; van Hest, J. C. M. Copper-Free Clickable Coatings Adv. Funct. Mat. 2009, 19, 3464-3470
80. Hong, V.; Kislukhin, A. A.; Finn, M. G. Thiol-Selective Fluorogenic Probes for Labeling and Release J. Am. Chem. Soc. 2009, 131, 9986-9994
81. Bernardin, A.; Cazet, A.; Guyon, L.; Delannoy, P.; Vinet, F.; Bonnaffé, F.; Texier, I. Copper-Free Click Chemistry for Highly Luminescent Quantum Dot Conjugates: Application to in Vivo Metabolic Imaging Bioconjugate Chem. 2010, 21, 583-588
82. DeForest, C. A.; Polizzotti, B. D.; Anseth, K. S. Sequential Click Reactions for Synthesizing and Patterning Three-Dimensional Cell Microenvironments Nat. Mater. 2009, 8, 659-664
83. Johnson, J. A.; Baskin, J. M.; Bertozzi, C. R.; Koberstein, J. T.; Turro, N. J. Copper-free Click Chemistry for the in Situ Crosslinking of Photodegradable Star Polymers Chem. Commun. 2008, 3064-3066 (Pubitemid 351904561)
84. Wilson, J. T.; Krishnamurthy, V. R.; Cui, W.; Qu, Z.; Chaikof, E. L. Noncovalent Cell Surface Engineering with Cationic Graft Copolymers J. Am. Chem. Soc. 2009, 131, 18228-18229
85. Ornelas, C.; Broichhagen, J.; Weck, M. Strain-Promoted Alkyne Azide Cycloaddition for the Functionalization of Poly(amide)-Based Dendrons and Dendrimers J. Am. Chem. Soc. 2010, 132, 3923-3931
86. Poloukhtine, A. A.; Mbua, N. E.; Wolfert, M. A.; Boons, G.-J.; Popik, V. V. Selective Labeling of Living Cells by a Photo-Triggered Click Reaction J. Am. Chem. Soc. 2009, 131, 15769-15776