Adenosine 2′-monophosphate, 5′-O-[S-(4- succinimidylbenzophenone)-thiophosphate]: A new photoaffinity label for the coenzyme site of porcine NADP-specific isocitrate dehydrogenase

Bioconjugate Chemistry

Volumn 16, Issue 3, 2005, Pages 650-659

  Lee, Peychii ^a   Colman, Roberta F ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CHLORINE COMPOUNDS; ENZYME ACTIVITY; IRRADIATION; THIN LAYER CHROMATOGRAPHY;

AMINO-ACIDS; COUPLING REACTION; DOUBLE MUTANTS; ISOCITRATE DEHYDROGENASE; MALEIMIDES; MASS SPECTROSCOPY; MUTANT ENZYMES; PHOTOAFFINITY; REACTIVE CYSTEINE; SYNTHESISED;

MASS SPECTROMETRY;

2' MONOPHOSPHOADENOSINE 5' DIPHOSPHORIBOSE; ADENOSINE 2' MONOPHOSPHATE, 5' O [S (4 SUCCINIMIDYL BENZOPHENONE) THIOPHOSPHATE]; AGENTS INTERACTING WITH TRANSMITTER, HORMONE OR DRUG RECEPTORS; ISOCITRATE DEHYDROGENASE; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; RIBOSE PHOSPHATE; UNCLASSIFIED DRUG; ADENOSINE; ADENOSINE 2' MONOPHOSPHATE, 5' O (S (4 SUCCINIMIDYLBENZOPHENONE) THIOPHOSPHATE); ADENOSINE 2'-MONOPHOSPHATE, 5'-O-(S-(4-SUCCINIMIDYLBENZOPHENONE)-THIOPHOSPHATE); CYSTEINE; DRUG DERIVATIVE; LIGAND; SUCCINIMIDE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; ENZYME ACTIVITY; ENZYME BINDING; ENZYME INACTIVATION; ENZYME KINETICS; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PHOSPHORYLATION; PHOTOAFFINITY LABELING; PROTEIN ANALYSIS; PROTEIN BINDING; SYNTHESIS; THIN LAYER CHROMATOGRAPHY; ULTRAVIOLET IRRADIATION; ANIMAL; BINDING SITE; CHEMISTRY; CIRCULAR DICHROISM; ENZYME ACTIVATION; GENETICS; ISOLATION AND PURIFICATION; KINETICS; METABOLISM; MUTATION; PROTEIN SECONDARY STRUCTURE; SWINE;

SUIDAE;

ADENOSINE; ANIMALS; BINDING SITES; CIRCULAR DICHROISM; CYSTEINE; ENZYME ACTIVATION; ISOCITRATE DEHYDROGENASE; KINETICS; LIGANDS; MOLECULAR STRUCTURE; MUTATION; NADP; PHOTOAFFINITY LABELS; PROTEIN STRUCTURE, SECONDARY; SUCCINIMIDES; SWINE;

EID: 18844406795     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc049722w     Document Type: Article

References (38)

1. Colman, R. F. (1997) Chemical arrows for enzymatic targets. FASEB J. 217-226.
2. Colman, R. F. (1997) Affinity labels for NAD(P)-specific sites. Methods in Enzymology, vol. 280, pp 186-203, Academic Press, New York.
3. Kumar, A., and Colman, R. F. (1994) 8-(4-Bromo-2,3-dioxobutylthio)NAD: a new affinity label for NAD-specific isocitrate dehydrogenase. Arch. Biochem. Biophys. 308, 357-366.
4. Dombrowski, K. E., and Colman, R. F. (1989) 5′-p-(Fluorosulfonyl) benzoyl-8-azidoadenosine: a new bifunctional affinity label for nucleotide binding sites in proteins. Arch. Biochem. Biophys. 275, 302-308.
5. Madhusoodanan, K. S., and Colman, R. F. (2001) Adenonsine 5′-O-[S-(4-succinimidyl-benzophenone)thiophosphate]: a new photoaffinity label of the allosteric ADP site of bovine liver glutamate dehydrogenase. Biochemistry 40, 1577-1586.
6. Dorman, G., and Prestwich, G. D. (1994) Benzophenone photophores in biochemistry. Biochemistry 33, 5661-5673.
7. Wang, J., Bauman, S., and Colman, R. F. (1998) Photoaffinity labeling of rat liver glutathinone S-transferase, 4-4, by glutathionyl S-[4-(succinimidyl)- benzophenone]. Biochemistry 37, 15671-15679.
8. Colman, R. F. (1983) Aspects of the structure and function of the isocitrate dehydrogenases. Peptide and Protein Review, vol. 1, pp 41-69, Marcel Dekker, Inc. New York.
9. + complexes. Biochemistry 30, 8671-8678.
10. 6-ethenoadenosine 2′,5′-bisphosphate. Biochemistry 24, 5367-5377.
11. Haselbeck, R. J., Colman, R. F., and McAlister-Henn, L. (1992) Isolation and sequence of a cDNA encoding porcine mitochondrial NADP-specific isocitrate dehydrogenase. Biochemistry 31, 6219-6223.
12. Kelly, J. H., and Plaut, G. W. E. (1981) Physcial evidence for the dimerization of the triphosphorylpyridine-specific isocitrate dehydrogenase from pig heart. J. Biol. Chem. 256, 330-334.
13. +-dependent isocitrate dehydrogenase. Acta Crystallogr. D52, 1024-1026.
14. 2+ and isocitrate. J. Biol. Chem. 277, 43454-43462.
15. 141 in the active site of Bacillus subitilis adenylosuccinate lyase by affinity labeling with 6-(4-bromo-2,3-dioxobutyl) thioadenosine 5′-monophosphate. J. Biol. Chem. 272, 458-465.
16. Deutsch, D. H., and Phillips, R. E. (1957) Preparation of tricarboxylic acids. Methods in Enzymology, vol. 3, pp 421-425, Academic Press, New York.
17. 35S]thiophosphoryl chloride production. Anal. Biochem. 209, 143-149.
18. Lee, P., Gorrell, A., Fromm, H. J., and Colman, R. F. (1999) 8-(4-Bromo-2,3-dioxobutylthio)guanosine 5′-triphosphate: a new affinity label for purine nucleotide sites in proteins. Arch. Biochem. Biophys. 372, 205-213.
19. Soundar, S., Danek, B. L., and Colman, R. F. (2000) Identification by mutagenesis of arginines in the substrate binding site of the porcine NADP-dependent isocitrate dehydrogenase. J. Biol. Chem. 275, 5606-5612.
20. Grodsky, N. B., Soundar, S., and Colman, R. F. (2000) Evaluation by site-directed mutagenesis of aspartic acid residues in the metal site of pig heart NADP-dependent isocitrate dehydrogenase. Biochemistry 39, 2193-2200.
21. 316 in the coenzyme site of pig mitochondrial NADP-dependent isocitrate dehydrogenase. Arch. Biochem. Biophys. 401, 81-90.
22. Laemmli, U. K. (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227, 680-685.
23. Bradford, M. M. (1976) A rapid and sensitive method for the quantitaion of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72, 248-254.
24. Penefsky, H. S. (1979) A centrifuged-column procedure for the measurement of ligand binding by beef heart F1. Methods in Enzymology, vol. 56, pp 527-530, Academic Press, New York.
25. +-dependent isocitrate dehydrogenase using resonance energy transfer. Biochemistry 26, 4893-4900.
26. Bailey, J. M., and Colman, R. F. (1987) 2[(4-bromo-2,3-dioxobutyl)thio]- and 2-[(3-bromo-2-oxopropyl)thio]adenosine 2′,5′-bisphosphate: new nucleotide analogue that act as affinity labels of nicotinamide adenine dinucleotide phosphate specific isocitrate dehydrogenase. Biochemistry 26, 6858-6869.
27. 319 in the coenzyme site of pig heart NADP-dependent isocitrate dehydrogenase. Biochemistry 41, 5637-5643.
28. Connolly, B. A., and Eckstein, F. (1982) S-methylated nucleoside phosphorothioates as probes of enzyme metal-nucleotide binding sites. Biochemistry 21, 6158-6167.
29. Smyth, G. E., and Colman, R. F. (1991) Cysteinyl peptides of pig heart NADP-dependent isocitrate dehydrogenase that are modified upon inaction by N-ethylmaleimide. J. Biol. Chem. 266, 14918-14925.
30. Smyth, G. E., and Colman, R. F. (1992) Inactivation of pig heart NADP-specific isocitrate dehydrogenase by two affinity reagents is due to reaction with a cysteine not essential for function. Arch. Biochem. Biophys. 293, 356-361.
31. +-specific isocitrate dehydrogenase. J. Biol. Chem. 262, 12620-12626.
32. Ehrlich, R. S., and Colman, R. F. (1975) Coenzyme binding by native and chemically modified pig heart triphosphopyridine nucleotide dependent isocitrate dehydrogenase. Biochemistry 14, 5008-5016.
33. Mas, M. T., and Colman, R. F. (1985) Spectroscopic studies of the interactions of coenzymes and coenzyme fragments with pig heart, oxidized triphosphopyridine nucleotide specific isotictrate dehydrogenase. Biochemistry 24, 1634-1646.
34. Stoddard, B. L., Dean, A., and Koshland, D. E. Jr. (1993) Structure of isocitrate dehydrogenase with isocitrate, nicotinamide adenine dinucleotide phosphate, and calcium at 2.5-Å resolution: a pseudo-Michaelis ternary complex. Biochemistry 32, 9310-9316.
35. Chen, R., Greer, A., and Dean, A. M. (1995) A highly active decarboxylating dehydrogenase with rationally inverted coenzyme specificity. Proc. Natl. Acad. Sci. U.S.A. 92, 11666-11670.
36. +-specific isocitrate dehydrogenase. Biochemistry 23, 1675-1683.
37. +. J. Biol. Chem. 278, 36897-36904.
38. Ehrlich, R. S., and Colman, R. F. (1978) Histidine in the nucleotide-binding site of NADP-linked isocitrate dehydrogenase from pig heart. Eur. J. Biochem. 89, 575-587.