Efficient solid-phase synthesis of Vpr from HIV-1 using low quantities of uniformly 13C-, 15N-labeled amino acids for NMR structural studies

Journal of Peptide Research

Volumn 54, Issue 5, 1999, Pages 427-435

  Cornille, F ^a   Wecker, K ^a   Loffet, A ^b   Genet, R ^c   Roques, Bernard ^a  

^a CNRS   (France)

^b Senn Chemicals AG   (Switzerland)

^c CEA SACLAY   (France)

Author keywords

Heteronuclear NMR; HIV; Solid phase peptide synthesis; Vpr

Indexed keywords

AMINO ACID; CARBON 13; NITROGEN 15; VPR PROTEIN;

APOPTOSIS; ARTICLE; CELL CYCLE; GENETIC TRANSCRIPTION; HUMAN IMMUNODEFICIENCY VIRUS 1; ISOTOPE LABELING; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN CONFORMATION; PROTEIN STRUCTURE; PROTEIN TRANSPORT;

AMINO ACID SEQUENCE; AMINO ACIDS; CARBON ISOTOPES; FLUORENES; GENE PRODUCTS, VPR; HIV-1; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR SEQUENCE DATA; NITROGEN ISOTOPES; PEPTIDE FRAGMENTS; PROTEIN CONFORMATION; PROTEIN STRUCTURE, SECONDARY;

HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1; RNA VIRUSES;

EID: 0032704310     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1034/j.1399-3011.1999.00129.x     Document Type: Article

References (39)

1. Cohen, E.A., Terwilliger, E.F., Jalinoos, Y., Proulx, J., Sodroski, J.G. & Haseltine, W.A. (1990b) Identification of HIV-1 vpr product and function. Acquir. Immun. Defic. Syndr. 3, 11-18.
2. Garrett, E.D., Tiley, L.S. & Cullen, B.R.(1991) Rev. activates expression of the human immunodeficiency virus type 1 vif and vpr gene products. J. Virol. 65, 1653-1657.
3. Cohen, E.A., Dehni, G., Sodroski, J.G. & Haseltine, W.A. (1990a) Human immunodeficiency virus vpr product is a virion-associated regulatory protein. J. Virol. 64, 3097-3099.
4. De Rocquigny, H., Petitjean, P., Tanchou, V., Decimo, D., Drouot, L., Delaunay, T., Darlix, J.L. & Roques, B.P. (1997) The zinc fingers of HIV nucleocapsid protein NCp7 direct interactions with the viral regulatory protein Vpr. J. Biol. Chem. 272, 30753-30759.
5. Wang, L., Mukherjee, S., Jia, F., Narayan, O. & Zhao, L.J. (1995) Interaction of virion protein Vpr of human immunodeficiency virus type 1 with cellular transcription factor Sp1 and trans-activation of viral long terminal repeat. J. Biol. Chem. 270, 25564-25569.
6. Agostini, I., Navarro, J.M., Rey, F., Bouhamdan, M., Spire, B., Vigne, R. & Sire, J. (1996) The human immunodeficiency virus type 1 Vpr transactivator: cooperation with promoter-bound activator domains and binding to TFIIB. J. Mol. Biol. 261, 599-606.
7. Connor, R.I., Chen, B.K., Choe, S. & Landau, N.R. (1995) Vpr is required for efficient replication of human immunodeficiency virus type-1 in mononuclear phagocytes. Virology 206, 935-944.
8. Emerman, H. (1996) HIV-1, Vpr and the cell cycle. Curr. Biol. 6, 1096-1103.
9. Stark, L.A. & Hay, R.T. (1998) Human immunodeficiency virus type 1 [HIV-1] viral protein R (Vpr) interacts with Lys-tRNA synthetase: implications for priming of HTV-1 reverse transcription, J. Virol. 72, 3037-3044.
10. Hu, T., Guan, T. & Gerace, L. (1996) Molecular and functional characterization of the p62 complex, an assembly of nuclear pore complex glycoproteins. J. Cell. Biol. 134, 589-601.
11. Zhang, S., Pointeg, D., Singer, G., Feng, Y., Park, K. & Zhao, L.J. (1998) Direct binding to nucleic acids by Vpr of human immunodeficiency virus type 1. Gene 212, 157-166.
12. Wang, L., Mukherjee, S., Narayan, O. & Zhao, L.J. (1996) Characterization of a leucine-zipper-like domain in Vpr protein of human immunodeficiency virus type 1. Gene 178, 7-13.
13. Schüler, W., Wecker, K., de Rocquigny, H., Baudat, Y., Sire, J. & Roques, B.P. (1999) NMR structure of the (52-96) C-terminal domain of the HTV-1 regulatory protein Vpr: molecular insights into its biological functions. J. Mol. Biol. 285, 2105-2117.
14. Mahalingam, S., Ayyavoo, V., Patel, M., Kieber-Emmons, T. & Weiner, D.B. (1997) Nuclear import, virion incorporation, and cell cycle arrest/differentiation are mediated by distinct functional domains of human immunodeficiency virus type 1 Vpr. J. Virol. 71, 6339-6347.
15. Macreadie, I.G., Castelli, I.A., Hewish, D.R., Kirkpatrick, A., Ward, A.C. & Azad, A.A. (1995) A domain of human immunodeficiency virus type 1 Vpr containing repeated H (S/F) RIG amino acid motifs causes cell growth arrest and structural defects. Proc. Natl Acad. Sci. USA 92, 2770-2774.
16. Nie, Z., Bergeron, D., Subbramanian, R.A., Yao, X.J., Checroune, F., Rougeau, N. & Cohen, E.A. (1998) The putative alpha helix a of human immunodeficiency virus type 1 Vpr contains a determinant which is responsible for the nuclear translocation of proviral DNA in growth-arrested cells. J. Virol. 72, 4104-4115.
17. Jowett, J.R.M., Planelles, V., Poon, B., Shah, N.P., Chen, M.L. & Chen, I.S.Y. (1995) The human immunodeficiency virus type 1 vpr gene arrests infected T cells in the G2 + M phase of the cell cycle. J. Virol. 69, 6304-6313.
18. Fukumori, T., Akari, H., Iida, S., Hata, S., Kagawa, S., Aida, Y., Koyama, A.H. & Adachi, A. (1998) The HTV-1 Vpr displays strong anti-apoptotic activity. FFBS Lett. 432, 17-20.
19. Tung, H.Y.L., de Rocquigny, H.; Zhao, L.J., Cayla, X., Roques, B.P. & Ozon, R. (1997) Direct activation of protein phosphatase-2Ao by HIV-1 encoded protein complex NCp7/Vpr. FEBS Lett. 401, 197-201.
20. Piller, S.C., Jans, P., Gage, P.W. & Jans, D.A. (1998) Extracellular HTV-1 virus protein R causes a large inward current and cell death in cultured hippocampal neurons: implications for AIDS pathology. Proc. Natl Acad. Sci. USA 98, 4595-4600.
21. Macreadie, I.G., Thorburn, D.R., Kirby, D.M., Castelli, L.A., de Rozario, N.L. & Azad, A.A. (1997) HIV-1 protein Vpr causes gross mitochondrial dysfunction in the yeast Saccharomyces cerevisiae. FERS Lett. 410, 145-149.
22. Atherton, E., Sheppard, R.C. (1989). Fluorenymethoxycarbonyl-amino acids. In Solid Phase Peptide Synthesis: A Practical Approach (Atherton, E. & Sheppard, R.C., eds.). IRL Press, Oxford, pp. 47-63.
23. Gras-masse, H., Amcisen, J.C., Boutillon, C., Gesquière, J.C., Vian, S., Neyrinck, J.L., Drobrecq, H., Capron, A. & Tartar, A. (1990) A synthetic protein corresponding to the entire vpr gene product from the human immunodeficiency virus HUM is recognized by antibodies from HIV-infected patients. Int. J. Peptide Protein Res. 36, 219-226.
24. Larsen, B.D. & Holm, A. (1994) Incomplete Fmoc deprotection in solid-phase synthesis of peptides. Int. J. Peptide Protein Res. 43, 1-9.
25. Johnson, T., Quibell, M. & Sheppard, R.C. (1995) N, O-bisFmoc derivatives of N-(2-hydroxy-4-methoxybenzyl)-amino acids: useful intermediates in peptide synthesis. J. Peptide Sci. 1, 11-25.
26. Hyde, C., Johnson, T., Owen, D., Quibell, M. & Sheppard, R.C. (1994) 'Difficult sequences' made easy - backbone protection in solid phase peptide synthesis. In Innovation and Perspectives in Solid Phase Synthesis Peptides, Proteins and Nucleic Acids (Epton, R., ed.). Mayflower Worldwide, Birmingham, AL, pp. 29-38.
27. Yang, Y., Sweeney, W.V., Schneider, K., Thörnqvist, S., Chait, B.T. & Tam, J.P. (1994) Aspartimide formation in base-driven 9-fluorenyimethoxycarbonyl chemistry. Tetrahedron Lett. 35, 9689-9692.
28. Zhao, L.J., Wang, L., Mukherjee, S. & Narayan, O. (1994) Biochemical mechanism of HIV-1 Vpr function. Oligomerization mediated by the N-terminal domain, J. Biol. Chem. 269, 32131-32137.
29. Segawa, S.I., Fukuno, T., Fujiwara, K. & Noda, Y. (1991) Local structures in unfolded lysozyme and correlation with secondary structures in the native conformation: helix-forming or -breaking propensity of peptide segments. Biopolymers 31, 497-509.
30. Dyson, H.J., Merutka, G., Waltho, J.P., Lerner, R.A. & Wright, P.E. (1992) Folding of peptide fragments comprising the complete sequence of proteins. Models for initiation of protein folding. I. Myohemerythrin. J. Mol. Biol. 226, 795-817.
31. Stewart, S.A., Poon, B., Jowett, J.B. & Chen, I.S. (1997) Human immunodeficiency virus type 1 Vpr induces apoptosis following cell cycle arrest. J. Virol. 71, 5579-5592.
32. 1 Vpr. Res. Virol. 148, 207-213.
33. Roques, B.P., Morellet, N., de Rucquigny, H., Déméné, H., Schüler, W. & Jullian, N. (1997) Structure, biological functions and inhibition of the HIV-1 proteins Vpr and NCp7. Biochimie 79, 673-680.
34. Merrifield, R.B. (1963) Solid phase peptide synthesis. I The synthesis of a tetrapeptide. J. Am. Chem. Soc. 85, 2149-2154.
35. Wang, S.-S. (1973) p-Alkoxyhenzyl alcohol resin and p-alkoxybenzyloxycarbonyl-hydraside resin for solid phase synthesis of protected peptide fragments. J. Am. Chem. Soc. 95, 1328-1333.
36. Griesinger, C., Otting, G., Wüthrich, K. & Ernst, R.R. (1988) Clean TOCSY for 1H spin system identification in macromolecules. J. Am. Chem. Soc. 110, 7870-7872.
37. Jeener, J., Meier, B.H., Bachmann, P. & Ernst, R.R. (1982) Investigation of exchange processes by two-dimensional NMR spectroscopy. J. Chem. Phys. 71, 4546-4553.
38. 1H spin-spin coupling constants in proteins. Biochem. Biophys. Res. Commun. 113, 967-974.
39. Bodenhausen, G. & Ruben, D.J. (1980) Natural abondance nitrogen-15 NMR enhanced heteronuclear spectroscopy. Chem. Phys. Lett. 69, 185-189.