EPR spectroscopic evidence for the mechanism-based inactivation of adenosylcobalamin-dependent diol dehydratase by coenzyme analogs

Journal of Biochemistry

Volumn 124, Issue 3, 1998, Pages 598-601

  Yamanishi, Mamoru ^a   Yamada, Seiki ^a   Ishida, Atsuhiko ^a   Yamauchi, Jun ^b   Toraya, Tetsuo ^a  

^a OKAYAMA UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

Adenosylcobalamin; Coenzyme B12; Diol dehydratase; Electron paramagnetic resonance; Mechanism based inactivation

Indexed keywords

APOENZYME; COBAMAMIDE; CYCLOPROPANE; HYDROLYASE; IMIDAZOLE DERIVATIVE; PROPYLENE GLYCOL;

ARTICLE; COENZYME; ELECTRON SPIN RESONANCE; ENZYME INACTIVATION; ENZYME MECHANISM; ENZYME SUBSTRATE;

EID: 0031665080     PISSN: 0021924X     EISSN: None     Source Type: Journal    
DOI: 10.1093/oxfordjournals.jbchem.a022153     Document Type: Article

References (16)

1. Lee, H.A., Jr. and Abeles, R.H. (1963) Purification and properties of dioldehydrase, an enzyme requiring a cobamide coenzyme. J. Biol. Chem. 238, 2367-2373
2. 12-dependent diol dehydrase: glycerol as both a good substrate and a potent inactivator. Biochem. Biophys. Res. Commun. 69, 475-480
3. 12-dependent isozymes. Metal Ions Biol. Systems 30, 217-254
4. 12. J. Biol. Chem. 248, 1285-1290
5. Valinsky, J.E., Abeles, R.H., and Mildvan, A.S. (1974) Electron spin resonance studies with dioldehydrase. II. The hyperfine structure of proposed radical intermediates derived from isotopic substitution in 2-chloroacetaldehyde. J. Biol. Chem. 249, 2751-2755
6. Valinsky, J.E., Abeles, R.H., and Fee, J.A. (1974) Electron spin resonance studies on diol dehydrase. 3. Rapid kinetic studies on the rate of formation of radicals in the reaction with propanediol. J. Am. Chem. Soc. 96, 4709-4710
7. 12 dependent reaction. J. Am. Chem. Soc. 94, 275-277
8. Toraya, T. and Ishida, A. (1991) Roles of the D-ribose and 5,6-dimethylbenzimidazole moieties of the nucleotide loop of adenosylcobalamin in manifestation of coenzymic function in the diol dehydrase reaction. J. Biol. Chem. 266, 5430-5437
9. Toraya, T., Miyoshi, S., Mori, M., and Wada, K. (1994) The synthesis of a pyridyl analog of adenosylcobalamin and its coenzymic function in the diol dehydratase reaction. Biochim. Biophys. Acta 1204, 169-174
10. Ishida, A. and Toraya, T. (1993) Adenosylcobinamide methyl phosphate as a pseudocoenzyme for diol dehydrase. Biochemistry 32, 1535-1540
11. 12 and analogs synthesized from hydridocobalamin. Biochem. J. 86, 2p-3p
12. Tobimatsu, T., Hara, T., Sakaguchi, M., Kishimoto, Y., Wada, Y., Isoda, M., Sakai, T., and Toraya, T. (1995) Molecular cloning, sequencing, and expression of the genes encoding adenosylcobalamin-dependent diol dehydrase of Klebsiella oxytoca. J. Biol. Chem. 270, 7142-7148
13. Tobimatsu, T., Sakai, T., Hashida, Y., Mizoguchi, N., Miyoshi, S., and Toraya, T. (1997) Heterologous expression, purification, and properties of diol dehydratase, an adenosylcobalamin-dependent enzyme of Klebsiella oxytoca. Arch. Biochem. Biophys. 347, 132-140
14. Toraya, T., Ushio, K., Fukui, S., and Hogenkamp, H.P.C. (1977) Studies on the mechanism of the adenosylcobalamin-dependent diol dehydrase reaction by the use of analogs of the coenzyme. J. Biol. Chem. 252, 963-970
15. Toraya, T., Yamanishi, M., Muguruma, H., Ushio, K., Yamauchi, J., and Kawamura, T. (1997) An electron paramagnetic resonance study on the mechanism-based inactivation of adenosylcobalamin-dependent diol dehydrase by glycerol and other substrates. Biochim. Biophys. Acta 1337, 11-16
16. 12. Biochim. Biophys. Acta 397, 510-518