Unnatural amino acid mutagenesis of GPCRs using amber codon suppression and bioorthogonal labeling

Methods in Enzymology

Volumn 520, Issue , 2013, Pages 281-305

  Huber, Thomas ^a   Naganathan, Saranga ^a   Tian, He ^a   Ye, Shixin ^a   Sakmar, Thomas P ^a  

^a ROCKEFELLER UNIVERSITY   (United States)

Author keywords

bioorthogonal; fluorescent label; Keywords; mutagenesis; unnatural amino acid

Indexed keywords

AMINO ACID; G PROTEIN COUPLED RECEPTOR; RHODOPSIN; UNCLASSIFIED DRUG; UNNATURAL AMINO ACID;

ANIMAL CELL; ARTICLE; CELL COUNT; CELL CULTURE; CODON; ENZYME ACTIVITY; ESCHERICHIA COLI; GENE REPRESSION; GEOBACILLUS STEAROTHERMOPHILUS; HUMAN; HUMAN CELL; MUTAGENESIS; NONHUMAN; PRIORITY JOURNAL; PROTEIN FUNCTION; PROTEIN MODIFICATION; SYNTHESIS;

EID: 84872559564     PISSN: 00766879     EISSN: 15577988     Source Type: Book Series    
DOI: 10.1016/B978-0-12-391861-1.00013-7     Document Type: Chapter

References (42)

1. N.J. Agard, J.M. Baskin, J.A. Prescher, A. Lo, and C.R. Bertozzi A comparative study of bioorthogonal reactions with azides ACS Chemical Biology 1 2006 644 648
2. B. Ahn, S.G. Rhee, and E.R. Stadtman Use of fluorescein hydrazide and fluorescein thiosemicarbazide reagents for the fluorometric determination of protein carbonyl groups and for the detection of oxidized protein on polyacrylamide gels Analytical Biochemistry 161 1987 245 257 (Pubitemid 17045972)
3. S. Banerjee, T. Huber, and T.P. Sakmar Rapid incorporation of functional rhodopsin into nanoscale apolipoprotein bound bilayer (NABB) particles Journal of Molecular Biology 377 2008 1067 1081
4. E.A. Bayer, H. Ben-Hur, and M. Wilchek Biocytin hydrazide - A selective label for sialic acids, galactose, and other sugars in glycoconjugates using avidin-biotin technology Analytical Biochemistry 170 1988 271 281
5. 2-adrenergic G protein-coupled receptor Science 318 2007 1258 1265 (Pubitemid 350172884)
6. J.W. Chin, T.A. Cropp, J.C. Anderson, M. Mukherji, Z.W. Zhang, and P.G. Schultz An expanded eukaryotic genetic code Science 301 2003 964 967 (Pubitemid 36994808)
7. V.W. Cornish, K.M. Hahn, and P.G. Schultz Site-specific protein modification using a ketone handle Journal of the American Chemical Society 118 1996 8150 8151 (Pubitemid 26305181)
8. K.A. Daggett, and T.P. Sakmar Site-specific in vitro and in vivo incorporation of molecular probes to study G-protein-coupled receptors Current Opinion in Chemical Biology 15 2011 392 398
9. M.F. Debets, S.S. Van Berkel, J. Dommerholt, A.J. Dirks, F.P.J.T. Rutjes, and F.L. Van Delft Bioconjugation with strained alkenes and alkynes Accounts of Chemical Research 44 2011 805 815
10. A.J. de Graaf, M. Kooijman, W.E. Hennink, and E. Mastrobattista Nonnatural amino acids for site-specific protein conjugation Bioconjugate Chemistry 20 2009 1281 1295
11. A. Deiters, T.A. Cropp, M. Mukherji, J.W. Chin, J.C. Anderson, and P.G. Schultz Adding amino acids with novel reactivity to the genetic code of Saccharomyces cerevisiae Journal of the American Chemical Society 125 2003 11782 11783 (Pubitemid 37175389)
12. A. Dirksen, T.M. Hackeng, and P.E. Dawson Nucleophilic catalysis of oxime ligation Angewandte Chemie International Edition 45 2006 7581 7584 (Pubitemid 44851688)
13. 2A receptor in complex with ZM241385 and the xanthines XAC and caffeine Structure 19 2011 1283 1293
14. P.A. Grimsrud, H.W. Xie, T.J. Griffin, and D.A. Bernlohr Oxidative stress and covalent modification of protein with bioactive aldehydes The Journal of Biological Chemistry 283 2008 21837 21841
15. A. Grunbeck, T. Huber, R. Abrol, B. Trzaskowski, W.A. Goddard III, and T.P. Sakmar Genetically-encoded photocrosslinkers map the binding site of a small molecule allosteric drug on a G protein-coupled receptor ACS Chemical Biology 7 2012 967 972
16. A. Grunbeck, T. Huber, P. Sachdev, and T.P. Sakmar Mapping the ligand-binding site on a G protein-coupled receptor (GPCR) using genetically encoded photocrosslinkers Biochemistry 50 2011 3411 3413
17. A. Grunbeck, T. Huber, and T.P. Sakmar Mapping the ligand binding sites using genetically encoded photoactivatable crosslinkers Methods in Enzymology 520 2012 305 320
18. T. Huber, A.V. Botelho, K. Beyer, and M.F. Brown Membrane model for the G-protein-coupled receptor rhodopsin: Hydrophobic interface and dynamical structure Biophysical Journal 84 2004 2078 2100 (Pubitemid 38524399)
19. T. Huber, and T.P. Sakmar Escaping the flatlands: New approaches for studying the dynamic assembly and activation of GPCR signaling complexes Trends in Pharmacological Sciences 32 2011 410 419
20. Huber, T., Ye, S., Naganathan, S., Kazmi, M. A., Duarte, T., & Sakmar, T. P., submitted. Bioorthogonal labeling of functional G protein-coupled receptors at genetically encoded keto and azido groups.
21. C. Joo, H. Balci, Y. Ishitsuka, C. Buranachai, and T. Ha Advances in single-molecule fluorescence methods for molecular biology Annual Review of Biochemistry 77 2008 51 76
22. M.A. Kazmi, L.A. Snyder, A.M. Cypess, S.G. Graber, and T.P. Sakmar Selective reconstitution of human D4 dopamine receptor variants with Giα subtypes Biochemistry 39 2000 3734 3744 (Pubitemid 30183855)
23. A.M. Knepp, A. Grunbeck, S. Banerjee, T.P. Sakmar, and T. Huber Direct measurement of thermal stability of expressed CCR5 and stabilization by small molecule ligands Biochemistry 50 2011 502 511
24. C. Köhrer, J.H. Yoo, M. Bennett, J. Schaack, and U.L. RajBhandary A possible approach to site-specific insertion of two different unnatural amino acids into proteins in mammalian cells via nonsense suppression Chemistry and Biology 10 2003 1095 1102 (Pubitemid 37496440)
25. S.T. Laughlin, N.J. Agard, J.M. Baskin, I.S. Carrico, P.V. Chang, and A.S. Ganguli Metabolic labeling of glycans with azido sugars for visualization and glycoproteomics Methods in Enzymology 415 2006 230 250 (Pubitemid 44751101)
26. S.T. Laughlin, and C.R. Bertozzi Metabolic labeling of glycans with azido sugars and subsequent glycan-profiling and visualization via Staudinger ligation Nature Protocols 2 2007 2930 2944
27. M. Meldal, and C.W. Tornoe Cu-catalyzed azide-alkyne cycloaddition Chemical Reviews 108 2008 2952 3015
28. Naganathan, S., Ye, S., Sakmar, T. P., & Huber, T., submitted. Site-specific epitope tagging of GPCRs by bioorthogonal modification of a genetically-encoded unnatural amino acid.
29. K. Palczewski, T. Kumasaka, T. Hori, C.A. Behnke, H. Motoshima, and B.A. Fox Crystal structure of rhodopsin: A G protein-coupled receptor Science 289 2000 739 745 (Pubitemid 30650186)
30. 2 adrenergic G-protein-coupled receptor Nature 450 2007 383 387 (Pubitemid 350126755)
31. 2 adrenergic receptor-Gs protein complex Nature 477 2011 549 555
32. P.J. Reeves, J. Hwa, and H.G. Khorana Structure and function in rhodopsin: Kinetic studies of retinal binding to purified opsin mutants in defined phospholipid- detergent mixtures serve as probes of the retinal binding pocket Proceedings of the National Academy of Sciences of the United States of America 96 1999 1927 1931 (Pubitemid 29117844)
33. V.O. Rodionov, S.I. Presolski, S. Gardinier, Y.H. Lim, and M.G. Finn Benzimidazole and related ligands for Cu-catalyzed azide-alkyne cycloaddition Journal of the American Chemical Society 129 2007 12696 12704 (Pubitemid 350004481)
34. E. Saxon, and C.R. Bertozzi Cell surface engineering by a modified Staudinger reaction Science 287 2000 2007 2010 (Pubitemid 30158675)
35. E. Saxon, S.J. Luchansky, H.C. Hang, C. Yu, S.C. Lee, and C.R. Bertozzi Investigating cellular metabolism of synthetic azidosugars with the Staudinger ligation Journal of the American Chemical Society 124 2002 14893 14902 (Pubitemid 36014096)
36. E.M. Sletten, and C.R. Bertozzi From mechanism to mouse: A tale of two bioorthogonal reactions Accounts of Chemical Research 44 2011 666 676
37. E.R. Stadtman, and R.L. Levine Free radical-mediated oxidation of free amino acids and amino acid residues in proteins Amino Acids 25 2003 207 218 (Pubitemid 38043943)
38. M.L. Tsao, F. Tian, and P.G. Schultz Selective staudinger modification of proteins containing p-azidophenylalanine ChemBioChem 6 2005 2147 2149
39. 2-adrenoceptor Gs complex Proceedings of the National Academy of Sciences of the United States of America 108 2011 16086 16091
40. B. Wu, E.Y.T. Chien, C.D. Mol, G. Fenalti, W. Liu, and V. Katritch Structures of the CXCR4 chemokine GPCR with small-molecule and cyclic peptide antagonists Science 330 2010 1066 1071
41. S. Ye, T. Huber, R. Vogel, and T.P. Sakmar FTIR analysis of GPCR activation using azido probes Nature Chemical Biology 5 2009 397 399
42. S. Ye, C. Köhrer, T. Huber, M. Kazmi, P. Sachdev, and E.C.Y. Yan Site-specific incorporation of keto amino acids into functional G protein-coupled receptors using unnatural amino acid mutagenesis The Journal of Biological Chemistry 283 2008 1525 1533