Formation of ubiquitin dimers via azide-alkyne click reaction

Methods in Molecular Biology

Volumn 832, Issue , 2012, Pages 589-596

  Eger, Silvia ^a   Scheffner, Martin ^a   Marx, Andreas ^a   Rubini, Marina ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

Artificial amino acids; Azidohomoalanine (Aha); Click reaction; Cu(I) catalyzed Huisgen azide alkyne cycloaddition; Pyrrolysine analogue (Plk); Triazole linkage; Ubiquitin chains

Indexed keywords

ALKYNE; AMINO ACID; AZIDE; POLYUBIQUITIN; TRANSFER RNA;

ARTICLE; CHEMISTRY; CLICK CHEMISTRY; GENETICS; METABOLISM; METHANOSARCINA BARKERI; METHODOLOGY; PROTEIN PROCESSING; SYNTHESIS; UBIQUITINATION;

ALKYNES; AMINO ACIDS; AZIDES; CLICK CHEMISTRY; METHANOSARCINA BARKERI; POLYUBIQUITIN; PROTEIN PROCESSING, POST-TRANSLATIONAL; RNA, TRANSFER; UBIQUITINATION;

EID: 84858166183     PISSN: 10643745     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-1-61779-474-2_41     Document Type: Article

References (23)

1. Hershko A, Ciechanover A (1998) The ubiquitin system. Annu. Rev. Biochem. 67 :425-479.
2. Hicke L, Dunn R (2003) Regulation of membrane protein transport by ubiquitin and ubiquitin-binding proteins. Annu. Rev. Cell. Dev. Biol. 19 :141-172.
3. Pickart CM (2001) Mechanisms underlying ubiquitylation. Annu. Rev. Biochem. 70 :503-533.
4. Kerscher O, Felberbaum R, Hochstrasser M (2006) Modifi cation of proteins by ubiquitin and ubiquitin-like proteins. Annu. Rev. Cell. Dev. Biol. 222 :159-180.
5. Peng J, Schwartz D, Elias JE et al (2003) A proteomics approach to understanding protein ubiquitination. Nat. Biotechnol. 21 :921-926.
6. Li W, Ye Y (2008) Polyubiquitin chains: Function, structures and mechanisms , Birkauser Verlag, Basel.
7. Hershko A, Ciechanover A (1992) The ubiquitin system for protein degradation. Annu. Rev. Biochem. 61 :761-807.
8. Williamson A, Wickliffe KE, Mellone BG et al (2009) Identifi cation of a physiological E2 module for the human anaphase-promoting complex. PNAS 106 :18213-18218.
9. Al-Hakim AK, Zagorska A, Chapman L et al (2008) Control of AMPK-related kinases by USP9X and atypical Lys29/Lys33-linked polyubiquitin chains. Journal of Biochemistry 411 :249-260.
10. Budisa N (2004) Prolegomena to future experimental efforts on genetic code engineering by expanding its amino acid repertoire. Angewandte Chemie International Edition 43 :6426-6463.
11. Young TS, Schultz PG (2010) Beyond the Canonical 20 Amino Acids: Expanding the Genetic Lexicon. J. Biol. Chem. 285 :11039-11044.
12. Kiick KL, Saxon E, Tirrell DA et al (2002) Incorporation of azides into revombinant proteins for chemosolective modifi cation by the Staudinger ligation. PNAS 99 :19-24.
13. Kasteren SIv, Kramer HB, Jensen HH et al (2007) Expanding the diversity of chemical protein modifi cation allows post-translational mimicry. Nature 446 :1105-1109.
14. Shanmugham A, Fish A, Luna-Vargas MPA et al (2010) Nonhydrolyzable ubiquitinisopeptide isosteres as deubiquitinating enzyme probes. J. Am. Chem. Soc. 132 :8834-8835.
15. Kaya E, Gutsmiedl K, Vrabel M et al (2009) Synthesis of Threefold Glycosylated Proteins using Click Chemistry and Genetically Encoded Unnatural Amino Acids. ChemBioChem 10 :2858-2861.
16. Nguyen DP, Lusic H, Neumann H et al (2009) Genetic Encoding and Labeling of Aliphatic Azides and Alkynes in Recombinant Proteins via a Pyrrolysyl-tRNA Synthetase/tRNACUA Pair and Click Chemistry. Journal of the American Chemical Society 131 :8720-8721.
17. Fekner T, Li X, Lee MM et al (2009) A Pyrrolysine Analogue for Protein Click Chemistry. Angew. Chem. Int. Ed. 48 :1633-1635.
18. Masson J-M, Miller JH (1986) Expression of synthetic suppressor tRNA genes under the control of a synthetic promoter. Gene 47 :179-183.
19. Young RA (1979) Transcription Termination in the Escherichia coli Ribosomal RNA Operon rrnC. THE JOURNAL OF BIOLOGICAL CHEMISTRY 254 :12725-12731.
20. Huisgen R (1963) 1,3-Dipolar Cycloadditions. Past and Future. Angew. Chem. Int. Ed. 2 :565-598.
21. Rostovtsev VV, Green LG, Fokin VV et al (2002) A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective Ligation of Azides and Terminal Alkynes. Angew. Chem. Int. Ed. 41 :2596-2599.
22. Tornoe CW, Christensen C, Meldal M (2002) Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecifi c copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J. Org. Chem. 67 :3057-3064.
23. Link AJ, Vink MKS, Tirrell DA (2007) Preparation of the functionoalized methionine surrogate azidohomoalanine via coppercatalyzed diazo transfer. Nature Protocols 2 :1879-1883.