Synthesis and fluorescence properties of Oregon Green 514 labeled peptides

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 20, 1999, Pages 2989-2994

  Delmotte, Caroline ^a   Delmas, Agnès ^a  

^a CENTRE DE BIOPHYSIQUE MOLÉCULAIRE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

6 CARBOXYFLUORESCEIN; CARBOXYLIC ACID; FLUORESCENT DYE; PEPTIDE; RESIN;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL LABELING; CONJUGATION; FLUORESCENCE ANALYSIS; MICROFLUOROMETRY; SOLID; SYNTHESIS;

BUFFERS; ELECTROCHEMISTRY; FLUORESCEINS; FLUORESCENT DYES; HYDROGEN-ION CONCENTRATION; MICELLES; OCTOXYNOL; PEPTIDES; SPECTROMETRY, FLUORESCENCE;

EID: 0033581598     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00512-0     Document Type: Article

References (17)

1. Song, L.; Hennink, E. J.; Young, I. T.; Tanke, H. J. Biophys. J. 1995, 68(6), 2588-2600
2. Sjöback, R.; Nygren, J.: Kubista, M. Spectrochim. Acta. A. 1995, 51, 7
3. Sun, W. C.; Gee, K. R.; Klaubert, D. H.; Haughland, R. P. J. Org. Chem. 1997, 62, 6469-6475.
4. Haugland, R. P. In Handbook of Fluorescent Probes and Research Chemicals; Spence, M. T. Z.; Molecular Probes: USA, 1996; Sixth Edition, pp 22-28, 562-564
5. Favard, C.; Valisa, P.; Egret-Charlier, M.; Sharonov, S.; Herben, C.; Manfait, M.; Da Silva, E.; Vigny, P. Biospectroscopy 1999, 5(2), 101-115
6. Sequence of the peptides used: TT-NP6: LSEIKGVIVHRLEGVLSEIKGVIVHR-LEGVLDRLVRLIG, TT: LSEIKGVIVHRLEGVLSEIKGVIVHRLEGV, T-NP6: LSEIKGVIVHRLEGVLDRLVRLIG;
7. Partidos, C.D.; Delmas, A.; and Steward, M.W., Mol Immunol. 1996, 33, 1223-1229.
8. Lelièvre, D.; Hsu, S. C.; Daubos, P.; Favard, C.; Vigny, P.; Trudelle, Y.; Steward, M. W.; Delmas, A. Eur. J. Biochem. 1997, 249, 895-904
9. Faure, M. P.; Gaudreau, P.; Shaw, I.; Cashman, N. R.; Beaudet, A. J. Histochem. Cytochem. 1994, 42, 755-763;
10. Kropshofer, H.; Bohlinger, I.; Max, H.; Kalbacher, H. Biochemistry 1991, 30, 9177- 9187.
11. Weber, P. J. A.; Bader, J. E.; Folkers, G.; Beck-Sickinger, G. B. Bioorg. Med. Chem. Lett. 1998, 8, 597- 600
12. Reagents: Oregon Green 514 carboxylic acid was obtained from Molecular Probes (Leiden, The Netherlands). Protected amino acids and resin were obtained from Senn Chemicals (Les Ulis, France) and Neosystem (Strasbourg, France) respectively. The chain side protections were as followed: tert-butyl (E, D, S), trityl (H), N-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl (R), tert-butoxycarbonyl (K). Peptides were synthesized on an ABI 431 A Applied Biosystems peptide Synthesizer. The mass spectrometer was a VG Quattro II type (Micromass) equipped with an electrospray ion source.
13. 6.
14. Lloyd-Williams, P.; Albericio, F.; Giralt, E. In Chemical Approches to the Synthesis of Peptides and Proteins, Rees, C. W. Ed; CRC Press LLC: Boca Raton, Florida, 1997; pp 48-56
15. Schnölzer, M.; Alewood, P.; Jones, A.; Alewood, D.; Kent, S. B. H. Int. J. Peptide Protein Res. 1992, 40, 180-193
16. Fluorescence spectroscopy was carried out at 20°C on a Fluoromax 2 (Jobin Yvon) fluorometer with a correction for excitation and emission spectra, using 5 mm pathlength quartz cuvettes, a Xenon lamp and 1 nm slits for excitation and emission.
17. Chen, R., F.; Arch. Biochem. Biophys. 1969, 133, 263-276