Organometallic palladium reagents for cysteine bioconjugation

Nature

Volumn 526, Issue 7575, 2015, Pages 687-691

  Vinogradova, Ekaterina V ^a   Zhang, Chi ^a   Spokoyny, Alexander M ^a,b   Pentelute, Bradley L ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; CYSTEINE; HALIDE; NUCLEOPHILE; ORGANOMETALLIC COMPOUND; ORGANOMETALLIC PALLADIUM; PALLADIUM COMPLEX; PEPTIDE; PERIODIC ACID; TRANSITION ELEMENT; TRASTUZUMAB; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG; DRUG; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; PALLADIUM; PROTEIN;

AMINO ACID; HALIDE; MOLECULAR ANALYSIS; PALLADIUM; PEPTIDE; SULFONATE; TRANSITION ELEMENT;

AFFINITY LABELING; ALLYLATION; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONJUGATION; CONTROLLED STUDY; CROSS COUPLING REACTION; EFFECTIVE CONCENTRATION; ELECTROPHILICITY; LOW TEMPERATURE; MASS SPECTROMETRY; MICHAEL ADDITION; OXIDATION; PH; PRIORITY JOURNAL; PROTEIN MODIFICATION; PROTEIN SYNTHESIS INHIBITION; REACTION TIME; CATALYSIS; CHEMISTRY; SYNTHESIS;

CATALYSIS; CHEMISTRY TECHNIQUES, SYNTHETIC; CYSTEINE; HYDROGEN-ION CONCENTRATION; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; PHARMACEUTICAL PREPARATIONS; PROTEINS;

EID: 84945561397     PISSN: 00280836     EISSN: 14764687     Source Type: Journal    
DOI: 10.1038/nature15739     Document Type: Article

References (30)

1. Crabtree, R. H. in The Organometallic Chemistry of the Transition Metals 6th edn (Wiley, 2014).
2. Diederich, F., Stang, P. J. Metal-catalyzed Cross-coupling Reactions (Wiley & Sons, 2008).
3. Antos, J. M., Francis, M. B. Transition metal catalyzed methods for site-selective protein modification. Curr. Opin. Chem. Biol. 10, 253-262 (2006).
4. Yang, M., Li, J., Chen, P. R. Transition metal-mediated bioorthogonal protein chemistry in living cells. Chem. Soc. Rev. 43, 6511-6526 (2014)
5. Walsh, C. T., Garneau-Tsodikova, S., Gatto, G. J. Protein posttranslational modifications: the chemistry of proteome diversifications. Angew. Chem. Int. Edn 44, 7342-7372 (2005).
6. Rabuka, D. Chemoenzymatic methods for site-specific protein modification. Curr. Opin. Chem. Biol. 14, 790-796 (2010).
7. Spicer, C. D., Davis, B. G. Selective chemical protein modification. Nature Commun. 5, 4740 (2014).
8. Chalker, J. M., Bernardes, G. J. L., Lin, Y. A., Davis, B. G. Chemical modification of proteins at cysteine: opportunities in chemistry and biology. Chem. Asian J. 4, 630-640 (2009).
9. Cal, P. M. S. D., Bernardes, G. J. L., Gois, P. M. P. Cysteine-selective reactions for antibody conjugation. Angew. Chem. Int. Edn 53, 10585-10587 (2014).
10. Toda, N., Asano, S., Barbas, C. F. Rapid, stable, chemoselective labeling of thiols with Julia-Kocieński-like reagents: a serum-stable alternative tomaleimide based protein conjugation. Angew. Chem. Int. Edn 52, 12592-12596 (2013).
11. Lyon, R. P. et al. Self-hydrolyzing maleimides improve the stability and pharmacological properties of antibody-drug conjugates. Nature Biotechnol. 32, 1059-1062 (2014).
12. Simmons, R. L., Yu, R. T., Myers, A. G. Storable arylpalladium(II) reagents for alkene labeling in aqueous media. J. Am. Chem. Soc. 133, 15870-15873 (2011).
13. Cheng, G., Lim, R. K. V., Li, N., Lin, Q. Storable palladacycles for selective functionalization of alkyne-containing proteins. Chem. Commun. 49, 6809-6811 (2013).
14. Barder, T. E., Biscoe, M. R., Buchwald, S. L. Structural insights into active catalyst structures and oxidative addition to (biaryl)phosphine-palladium complexes via density functional theory and experimental studies. Organometallics 26, 2183-2192 (2007).
15. Lee, C.-F., Liu, Y.-C., Badsara, S. S. Transition-metal-catalyzed C-S bond coupling reaction. Chem. Asian J. 9, 706-722 (2014).
16. Bong, D. T., Ghadiri, M. R. Chemoselective Pd(0)-catalyzed peptide coupling in water. Org. Lett. 3, 2509-2511 (2001).
17. Korneeva, E. N., Ovchinnikov,M. V., Kostić, N.M. Peptide hydrolysis promoted by polynuclear and organometallic complexes of palladium(II) and platinum(II). Inorg. Chim. Acta 243, 9-13 (1996).
18. Tilley, S. D., Francis, M. B. Tyrosine-selective protein alkylation using p-allylpalladium complexes. J. Am. Chem. Soc. 128, 1080-1081 (2006).
19. Shafer, D. E., Inman, J. K., Lees, A. Reaction of tris(2-carboxyethyl)phosphine (TCEP) with maleimide and a-haloacyl groups: anomalous elution of TCEP by gel filtration. Anal. Biochem. 282, 161-164 (2000).
20. Gorin, G., Martic, P. A., Doughty, G. Kinetics of the reaction of N-ethylmaleimide with cysteine and some congeners. Arch. Biochem. Biophys. 115, 593-597 (1966).
21. Gilbreth, R. N., Koide, S. Structural insights for engineering binding proteins based on non-antibody scaffolds. Curr. Opin. Struct. Biol. 22, 413-420 (2012).
22. Kung, K. K.-Y. et al. Cyclometalated gold(III) complexes for chemoselective cysteine modification via ligand controlled C-S bond-forming reductive elimination. Chem. Commun. 50, 11899-11902 (2014).
23. Arora, N., Leppla, S. H. Fusions of anthrax toxin lethal factor with shiga toxin and diphtheria toxin enzymatic domains are toxic to mammalian cells. Infect. Immun. 62, 4955-4961 (1994).
24. Bird, G. H., Gavathiotis, E., LaBelle, J. L., Katz, S. G., Walensky, L. D. Distinct BimBH3 (BimSAHB) stapled peptides for structural and cellular studies. ACS Chem. Biol. 9, 831-837 (2014).
25. Verdine, G. L., Hilinski, G. J. Stapled peptides for intracellular drug targets. Methods Enzymol. 503, 3-33 (2012).
26. Lau, Y. H., de Andrade, P.,Wu, Y., Spring, D. R. Peptide stapling techniques based on different macrocyclization chemistries. Chem. Soc. Rev. 44, 91-102 (2015).
27. Writing the macrocycle manual. Nature Chem. Biol. 10, 693 (2014).
28. Spokoyny, A. M. et al. A perfluoroaryl-cysteine SNAr chemistry approach to unprotected peptide stapling. J. Am. Chem. Soc. 135, 5946-5949 (2013).
29. Chari, R. V. J., Miller, M. L., Widdison, W. C. Antibody-drug conjugates: an emerging concept in cancer therapy. Angew. Chem. Int. Edn 53, 3796-3827 (2014).
30. Sun,M. M. C. et al. Reduction-alkylation strategies for the modification of specific monoclonal antibody disulfides. Bioconjug. Chem. 16, 1282-1290 (2005).