Purification of prenylated proteins by affinity chromatography on cyclodextrin-modified agarose

Analytical Biochemistry

Volumn 386, Issue 1, 2009, Pages 1-8

  Chung, Jinhwa A ^a   Wollack, James W ^a   Hovlid, Marisa L ^a   Okesli, Ayse ^a   Chen, Yan ^a   Mueller, Joachim D ^a   Distefano, Mark D ^a   Taton, T Andrew ^a  

^a University of Minnesota   (United States)

Author keywords

Affinity chromatography; Cyclodextrin; FPLC; Prenylation; Sepharose

Indexed keywords

AFFINITY CHROMATOGRAPHY; COLUMN CHROMATOGRAPHY; CYCLODEXTRINS; LANTHANUM COMPOUNDS; MASS SPECTROMETRY; PROTEINS; PURIFICATION; SUBSTRATES;

ELECTROSPRAY MASS SPECTROMETRY; FAST PROTEIN LIQUID CHROMATOGRAPHY; FPLC; ISOPRENOID SUBSTRATES; PRENYLATION; PRENYLATION REACTIONS; PROTEIN PRENYLATION; SEPHAROSE;

LIQUID CHROMATOGRAPHY;

AGAROSE; BETA CYCLODEXTRIN; CELL EXTRACT; ISOPRENOID; SEPHAROSE;

AFFINITY CHROMATOGRAPHY; ANALYTIC METHOD; ARTICLE; CARBOXY TERMINAL SEQUENCE; CELL LYSATE; CHEMICAL REACTION; CONTROLLED STUDY; CROSS LINKING; ELECTROSPRAY MASS SPECTROMETRY; ENZYME SUBSTRATE; FAST PROTEIN LIQUID CHROMATOGRAPHY; FEMALE; HELA CELL; HUMAN; HUMAN CELL; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN ISOLATION; PROTEIN PRENYLATION; PROTEIN PURIFICATION; PROTEIN TARGETING;

EID: 58349094493     PISSN: 00032697     EISSN: 10960309     Source Type: Journal    
DOI: 10.1016/j.ab.2008.09.007     Document Type: Article

References (47)

1. Lane K.T., and Beese L.S. Structural biology of protein farnesyltransferase and geranylgeranyltransferase type I. J. Lipid Res. 47 (2006) 681-699
2. Zhang F.L., and Casey P.J. Protein prenylation: molecular mechanisms and functional consequences. Annu. Rev. Biochem. 65 (1996) 241-269
3. Roskoski R. Protein prenylation: a pivotal posttranslational process. Biochem. Biophys. Res. Commun. 303 (2003) 1-7
4. Wright L.P., and Philips M.R. CAAX modification and membrane targeting of Ras. J. Lipid Res. 47 (2006) 883-891
5. Silvius J.R. Mechanisms of Ras protein targeting in mammalian cells. J. Membr. Biol. 190 (2002) 83-92
6. Resh M.D. Trafficking and signaling by fatty-acylated and prenylated proteins. Nat. Chem. Biol. 2 (2006) 584-590
7. Gelb M.H., Brunsveld L., Hrycyna C.A., Michaelis S., Tamanoi F., Van Voorhis W.C., and Waldmann H. Therapeutic intervention based on protein prenylation and associated modifications. Nat. Chem. Biol. 2 (2006) 518-528
8. Duckworth B.P., Chen Y., Wollack J.W., Sham Y., Mueller J.D., Taton T.A., and Distefano M.D. A universal method for the preparation of covalent protein-DNA conjugates for use in creating protein nanostructures. Angew. Chem. Intl. Ed. 46 (2007) 8819-8822
9. Duckworth B.P., Xu J., Taton T.A., Guo A., and Distefano M.D. Site-specific, covalent attachment of proteins to a solid surface. Bioconj. Chem. 17 (2006) 967-974
10. Xu J., Degraw A.J., Duckworth B.P., Lenevich S., Tann C.-M., Jenson E.C., Gruber S.J., Barany G., and Distefano M.D. Synthesis and reactivity of 6,7-dihydrogeranylazides: reagents for primary azide incorporation into peptides and subsequent Staudinger ligation. Chem. Biol. Drug Des. 68 (2006) 85-96
11. Rose M.W., Rose N.D., Boggs J., Lenevich S., Xu J., Barany G., and Distefano M.D. Evaluation of geranylazide and farnesylazide diphosphate for incorporation of prenylazides into a CAAX box-containing peptide using protein farnesyltransferase. J. Peptide Res. 65 (2005) 529-537
12. Rose M.W., Xu J., Kale T.A., O'Doherty G., Barany G., and Distefano M.D. Enzymatic incorporation of orthogonally reactive prenylazide groups into peptides using geranylazide diphosphate via protein farnesyltransferase: implications for selective protein labeling. Biopolymers 80 (2005) 164-171
13. 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. A tagging-via-substrate technology for detection and proteomics of farnesylated proteins. Proc. Natl. Acad. Sci. USA 101 (2004) 12479-12484
14. Duckworth B.P., Zhang Z., Hosokawa A., and Distefano M.D. Selective labeling of proteins by using protein farnesyltransferase. ChemBioChem 8 (2007) 98-105
15. Labadie G.R., Viswanathan R., and Poulter C.D. Farnesyl diphosphate analogues with ω-bioorthogonal azide and alkyne functional groups for protein farnesyl transferase-catalyzed ligation reactions. J. Org. Chem. 72 (2007) 9291-9297
16. Gauchet C., Labadie G.R., and Poulter C.D. Regio- and chemoselective covalent immobilization of proteins through unnatural amino acids. J. Am. Chem. Soc. 128 (2006) 9274-9275
17. Dursina B., Reents R., Delon C., Wu Y., Kulharia M., Thutewohl M., Veligodsky A., Kalinin A., Evstifeev V., Ciobanu D., Szedlacsek S.E., Waldmann H., Goody R.S., and Alexandrov K. Identification and specificity profiling of protein prenyltransferase inhibitors using new fluorescent phosphoisoprenoids. J. Am. Chem. Soc. 128 (2006) 2822-2835
18. Dursina B.-E., Reents R., Niculae A., Veligodsky A., Breitling R., Pyatkov K., Waldmann H., Goody R.S., and Alexandrov K. A genetically encodable microtag for chemo-enzymatic derivatization and purification of recombinant proteins. Protein Express. Purif. 39 (2005) 71-81
19. Turek-Etienne T.C., Strickland C.L., and Distefano M.D. Biochemical and structural studies with prenyl diphosphate analogues provide insights into isoprenoid recognition by protein farnesyltransferase. Biochemistry 42 (2003) 3716-3724
20. Nguyen U.T.T., Cramer J., Gomis J., Reents R., Gutierrez-Rodriguez M., Goody R.S., Alexandrov K., and Waldmann H. Exploiting the substrate tolerance of farnesyltransferase for site-selective protein derivatization. ChemBioChem 8 (2007) 408-423
21. Krzysiak A.J., Rawat D.S., Scott S.A., Pais J.E., Handley M., Harrison M.L., Fierke C.A., and Gibbs R.A. Combinatorial modulation of protein prenylation. ACS Chem. Biol. 2 (2007) 385-389
22. Bordier C. Phase-separation of integral membrane proteins in Triton X-114 solution. J. Biol. Chem. 256 (1981) 1604-1607
23. Casey P.J., Solski P.A., Der C.J., and Buss J.E. P21ras is modified by a farnesyl isoprenoid. Proc. Natl. Acad. Sci. USA 86 (1989) 8323-8327
24. Finkielstein C.V., Overduin M., and Capelluto D.G.S. Cell migration and signaling specificity is determined by the phosphatidylserine recognition motif of Rac1. J. Biol. Chem. 281 (2006) 27317-27326
25. Gorzalczany Y., Sigal N., Itan M., Lotan O., and Pick E. Targeting of Rac1 to the phagocyte membrane is sufficient for the induction of NADPH oxidase assembly. J. Biol. Chem. 275 (2000) 40073-40081
26. Rak A., Niculae A., Kalinin A., Thoma N.H., Sidorovitch V., Goody R.S., and Alexandrov K. In vitro assembly, purification, and crystallization of the Rab geranylgeranyl transferase:substrate complex. Protein Express. Purif. 25 (2002) 23-30
27. Nguyen T., Joshi N.S., and Francis M.B. An affinity-based method for the purification of fluorescently-labeled biomolecules. Bioconj. Chem. 17 (2006) 869-872
28. Connors K.A. Population characteristics of cyclodextrin complex stabilities in aqueous solution. J. Pharm. Sci. 84 (1995) 843-848
29. Davisson V.J., Woodside A.B., Neal T.R., Stremler K.E., Muehlbacher M., and Poulter C.D. Phosphorylation of isoprenoid alcohols. J. Org. Chem. 51 (1986) 4768-4779
30. Mayer M.P., Prestwich G.D., Dolence J.M., Bond P.D., Hong-yu W., and Poulter C.D. Protein farnesyltransferase: production in Escherichia coli and immunoaffinity purification of the heterodimer from Saccharomyces cerevisiae. Gene 132 (1993) 41-47
31. DeGraw A.J., Zhao Z., Strickland C.L., Taban A.H., Hsieh J., Jefferies M., Xie W., Shintani D.K., McMahan C.M., Cornish K., and Distefano M.D. A photoactive isoprenoid diphosphate analogue containing a stable phosphonate linkage: synthesis and biochemical studies with prenyltransferases. J. Org. Chem. 72 (2007) 4587-4595
32. Gomez R., Goodman L.E., Tripathy S.K., O'Rourke E., Manne V., and Tamanoi F. Purified yeast protein farnesyltransferase is structurally and functionally similar to its mammalian counterpart. Biochem. J. 289 (1993) 25-31
33. Chan T.R., Hilgraf R., Sharpless K.B., and Fokin V.V. Polytriazoles as copper(I)-stabilizing ligands in catalysis. Org. Lett. 6 (2004) 2853-2855
34. Shaner N.C., Campbell R.E., Steinbach P.A., Giepmans B.N.G., Palmer A.E., and Tsien R.Y. Improved monomeric red, orange, and yellow fluorescent proteins derived from Discosoma sp. red fluorescent protein. Nat. Biotechnol. 22 (2004) 1567-1572
35. Wilder D.R., Tindall G.W., Cunningham L.J., and Little J.L. High-performance liquid chromatographic analysis of sulfonated aromatics using a β-cyclodextrin-bonded phase. J. Chromatogr. 635 (1993) 221-226
36. Wang Q., Chan T.R., Hilgraf R., Fokin V.V., Sharpless K.B., and Finn M.G. Bioconjugation by copper(I)-catalyzed azide-alkyne [3+2] cycloaddition. J. Am. Chem. Soc. 125 (2003) 3192-3193
37. Kolb H.C., Finn M.G., and Sharpless K.B. Click chemistry: diverse chemical function from a few good reactions. Angew. Chem. Intl. Ed. 40 (2001) 2004-2021
38. 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. Identification of palmitoylated mitochondrial proteins using a bio-orthogonal azido-palmitate analogue. FASEB J. 22 (2008) 721-732
39. Martin D.D.O., Vilas G.L., Prescher J.A., Rajaiah G., Falck J.R., Bertozzi C.R., and Berthiaume L.G. Rapid detection, discovery, and identification of post-translationally myristoylated proteins during apoptosis using a bio-orthogonal azidomyristate analog. FASEB J. 22 (2008) 797-806
40. Wirtz J., and Kolter T. Novel tools for the proteomic identification of acylated proteins. ChemBioChem 8 (2007) 1631-1635
41. Troutman J.M., Roberts M.J., Andres D.A., and Spielmann H.P. Tools to analyze protein farnesylation in cells. Bioconj. Chem. 16 (2005) 1209-1217
42. Zhao Y., Zhang W., Kho Y., and Zhao Y. Proteomic analysis of integral plasma membrane proteins. Anal. Chem. 76 (2004) 1817-1823
43. Epstein W.W., Lever D., Leining L.M., Bruenger E., and Rilling H.C. Quantitation of prenylcysteines by a selective cleavage reaction. Proc. Natl. Acad. Sci. USA 88 (1991) 9668-9670
44. Pais J.E., Bowers K.E., Stoddard A.K., and Fierke C.A. A continuous fluorescent assay for protein prenyltransferases measuring diphosphate release. Anal. Biochem. 345 (2005) 302-311
45. Chowdhury S.K., Katta V., Beavis R.C., and Chait B.T. Origin and removal of adducts (molecular mass = 98 U) attached to peptide and protein ions in electrospray ionization mass spectra. J. Am. Soc. Mass Spectrom. 1 (1990) 382-388
46. Stephenson Jr. J.L., and McLuckey S.A. Ion/Ion proton transfer reactions for protein mixture analysis. Anal. Chem. 68 (1996) 4026-4032
47. Fountoulakis M., Vilbois F., Oesterhelt G., and Vetter W. Phosphoric acid entrapment leads to apparent protein heterogeneity. Bio/Technology 13 (1995) 383-388