Affinity labeling of dehydrogenases has been achieved with various reactive groups bound to nucleotide pyrophosphates. Bromoketones react preferentially with sulfhydryl-groups of the protein (Jörnvall, et al., 1975; von Bahr-Lindström, et al., 1985). In the case of lactate dehydrogenase modification, the small molecule 3-bromoacetylpyridine is attached to the imidazole part of an essential histidine (Berghäuser, et al., 1971).
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Berghäuser, J., Falderbaum, I., and Woenckhaus, C., 1971, Zuordnung eines essentiellen Histidinrestes der Lactat-Dehydrogenase zur Substratbindungsstelle, Hoppe-Sevler’s Z. Physiol. Chem., 352: 52.
Berghäuser, J., 1975, A Reactive Arginine in Adenylate Kinase, Biochim. Biophys. Acta, 397: 370.
Burkhard, A., Dworsky, A., Jeck, R., Pfeiffer, M., Pundak, S., and Woenckhaus, C., 1981, Diazoniumderivate des ADP zur Identifizierung essentieller Aminosäureseitenreste im aktiven Zentrum von Dehydrogenasen, Hoppe Sevier’s Z. Phvsiol. Chem., 362: 1079.
Chen, S., and Guillory, R., 1977, Arylazido-ß-alanine NAD+, a NAD+ Photoaffinity Analogue, J. Biol. Chem., 252: 8990.
Heiland, I., and Brauer, D., 1976, Primary Structure of Protein L 10 from the Large Subunit of Escherichia Coli Ribosomes, Hoppe-Sevler’s Z. Physiol. Chem., 357: 1751.
Hempel, J., and Pietruszko, R., 1981, Selective Chemical Modification of Human Liver Aldehyde Dehydrogenase E1 and E2 by Iodoacetamide, J. Biol. Chem., 256: 10889.
Hempel, J., Kaiser, R., and Jörnvall, H., 1985, Mitochondrial aldehyde dehydrogenase from human liver, Primary structure, differences in relation to the cytosolic enzyme, and functional correlations, Eur. J. Biochem. 153: 13.
Jeck, R., 1977, The Properties of [(3-Acetylpyridinium)-n-alkyl] Adenosine Pyrophosphates, Structural Analogs of the Coenzyme NAD+, Z. Naturforsch., 32c: 550.
Jornvall, H., Woenckhaus, C., and Johnscher, G., 1975, Modification of Alcohol Dehydrogenase with a Reactive Coenzyme Analogue, Eur. J. Biochem., 53: 71.
King, S., Kim, H., and Haley, B., 1991, Strategies and Reagents for Photoaffinity Labeling of Mechanochemical Proteins, “Methods in Enzymology”, Vol. 196, R. B. Vallee, ed., Academic Press Inc. p. 449.
Koberstein, R., 1976, 8-Azidoadenine Analogs of NAD+ and FAD; Synthesis and Coenzyme Properties with NAD+-Dependent and FAD-Dependent Enzymes, Eur. J. Biochem., 67: 223.
Tu, G., C., and Weiner, H., 1988, Evidence for Two Distinct Active Sites on Aldehyde Dehydrogenase, J. Biol. Chem., 263: 1218.
Tu, G., C., and Weiner, H., 1988, Evidence for Two Distinct Active Sites on Aldehyde Dehydrogenase, J. Biol. Chem., 263: 1218.
von Bahr-Lindström, H., Jeck, R., Woenckhaus, C., Sohn, S., Hempel, J., and Jörnvall, H., 1985, Characterization of the Coenzyme Binding Site of Liver Aldehyde Dehydrogenase: Differential Reactivity of Coenzyme Analogues, Biochemistry, 24: 5847.
Woenckhaus, C., Bieber, E., and Jeck, R., 1987, Studies on the Inactivation of Aldehyde Dehydrogenase (ALDH), in “Enzymology and Molecular Biology of Carbonyl Metabolism”, H. Weiner and T. G. Flynn, eds., Alan R. Liss, New York, p. 53.
Woenckhaus, C., and Filbrich, R., 1990, Photoaffinity Labeling of Lactate Dehydrogenase by the Bisazido Analog of NAD+: P1-N6(4-azidophenylethyl)adenosine-P2-[4-(3-azidopyridinio)butyl]diphosphate, Z. Naturforsch., 45C: 1044.
Yoshikawa, M., Kato, T., and Takenishi, T., 1967, A Novel Method For Phosphorylation of Nucleosides To 5′-Nucleotides, Tetrahedron Letters, 50: 5065.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1993 Springer Science+Business Media New York
About this chapter
Cite this chapter
Woenckhaus, C., Leibrock, H., Becker, S. (1993). Photoaffinity Labeling of Aldehyde Dehydrogenase from Horse Liver by P1-N6-(4-Azidophenylethyl)adenosine-P2-[4-(3-Azidopyridinio)Butyl] Diphosphate. In: Weiner, H., Crabb, D.W., Flynn, T.G. (eds) Enzymology and Molecular Biology of Carbonyl Metabolism 4. Advances in Experimental Medicine and Biology, vol 328. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-2904-0_23
Download citation
DOI: https://doi.org/10.1007/978-1-4615-2904-0_23
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4613-6259-3
Online ISBN: 978-1-4615-2904-0
eBook Packages: Springer Book Archive