Specific labeling of polypeptides at amino-terminal cysteine residues using Cy5-benzyl thioester

Bioconjugate Chemistry

Volumn 13, Issue 5, 2002, Pages 1039-1043

  Schuler, Benjamin ^a   Pannell, Lewis K ^a  

^a NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOSYNTHESIS; ENERGY TRANSFER; ESTERS; PEPTIDES; POLYPEPTIDES;

BENZYL MERCAPTAN; CYSTEINE RESIDUES; FLUORESCENT DYES; LABELINGS; LYSINE RESIDUES; SINGLE PROBE; SUCCINIMIDYL ESTER; TERMINAL CYSTEINE; THIOESTERS; TRIMETHYL ALUMINUMS;

AMINO ACIDS;

CARBOCYANINE; CY5 BENZYL THIOESTER; CY5-BENZYL THIOESTER; CYANINE DYE 5; CYSTEINE; DRUG DERIVATIVE; ESTER; FLUORESCENT DYE; PEPTIDE;

ARTICLE; CHEMISTRY; KINETICS; MOLECULAR PROBE; SYNTHESIS;

CARBOCYANINES; CYSTEINE; ESTERS; FLUORESCENT DYES; KINETICS; MOLECULAR PROBES; PEPTIDES;

EID: 0036738673     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc025509t     Document Type: Article

References (19)

1. Cohen, T., and Gapinski, R. E. (1978) The conversion of esters to phenyl thioesters by boron thiophenoxide and aluminum thiophenoxide. Tetrahedron Lett. 45, 4319-4322.
2. Corey, E. J., and Beames, D. J. (1973) A method for the protection of lactones and esters against nucleophilic attack. J. Am. Chem. Soc. 95, 5829-5831.
3. Dawson, P. E., Churchill, M. J., Ghadiri, M. R., and Kent, S. B. H. (1997) Modulation of reactivity in native chemical ligation through the use of thiol additives. J. Am. Chem. Soc. 119, 4325-4329.
4. Dawson, P. E., and Kent, S. B. (2000) Synthesis of native proteins by chemical ligation. Annu. Rev. Biochem. 69, 923-960.
5. Dawson, P. E., Muir, T. W., Clark-Lewis, I., and Kent, S. B. (1994) Synthesis of proteins by native chemical ligation. Science 266, 776-779.
6. Deniz, A. A., Laurence, T. A., Beligere, G. S., Dahan, M., Martin, A. B., Chemla, D. S., Dawson, P. E., Schultz, P. G., and Weiss, S. (2000) Single-molecule protein folding: Diffusion fluorescence resonance energy transfer studies of the denaturation of chymotrypsin inhibitor 2. Proc. Natl. Acad. Sci. U.S.A. 97, 5179-5184.
7. Erlanson, D. A., Chytil, M., and Verdine, G. L. (1996) The leucine zipper domain controls the orientation of AP-1 in the NFAT.AP-1.DNA complex. Chem. Biol. 3, 981-991.
8. Gill, S. C., and von Hippel, P. H. (1989) Calculation of protein extinction coefficients from amino acid sequence data. Anal. Biochem. 182, 319-326.
9. Gruber, H. J., Hahn, C. D., Kada, G., Riener, C. K., Harms, G. S., Ahrer, W., Dax, T. G., and Knaus, H. G. (2000) Anomalous fluorescence enhancement of Cy3 and Cy3.5 versus anomalous fluorescence loss of Cy5 and Cy7 upon covalent linking to IgG and noncovalent binding to avidin. Bioconjugate Chem. 11, 696-704.
10. Ha, T. (2001) Single-molecule fluorescence resonance energy transfer. Methods 25, 78-86.
11. Hackeng, T. M., Dawson, P. E., Griffin, J. H., Kent, S. B. H. (1997) Total chemical synthesis of enzymatically active human type II secretory phospholipase A2. Proc. Natl. Acad. Sci. U.S.A. 94, 7845-7850.
12. Hatch, P. H., and Weinreb, S. M. (1977) Preparation of tert-Butyl Thioesters. J. Org. Chem. 42, 3960-3961.
13. Haugland, R. (2001) Handbook of fluorescent probes and research chemicals, Molecular Probes, Inc., Eugene, OR
14. Hermanson, G. T. (1996) Bioconjugate Techniques, Academic Press, London.
15. Mujumdar, R. B., Ernst, L. A., Mujumdar, S. R., Lewis, C. J., and Waggoner, A. S. (1993) Cyanine dye labeling reagents: sulfoindocyanine succinimidyl esters. Bioconjugate Chem. 4, 105-111.
16. Perler, F. B., Xu, M. Q., and Paulus, H. (1997) Protein splicing and autoproteolysis mechanisms. Curr. Opin. Chem. Biol. 1, 292-299.
17. Rudolph, R., Böhm, G., Lilie, H., and Jaenicke, R. (1997) Folding proteins. In: Protein Function. A Practical Approach (T. E. Creighton, Ed.) pp 57-99, Oxford University Press, Oxford.
18. Watt, R. M., and Voss, E. W., Jr. (1977) Mechanism of quenching of fluorescein by anti-fluorescein IgG antibodies. Immunochemistry 14, 533-551.
19. Weiss, S. (1999) Fluorescence spectroscopy of single biomolecules. Science 283, 1676-1683.