Dismutase activity of ADP-L-glycero-D-manno-heptose 6-epimerase: Evidence for a direct oxidation/reduction mechanism

Biochemistry

Volumn 44, Issue 15, 2005, Pages 5907-5915

  Morrison, James P ^a   Read, Jay A ^a   Coleman Jr , William G ^b   Tanner, Martin E ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

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

Author keywords

[No Author keywords available]

Indexed keywords

BIOSYNTHESIS; CATALYSIS; HYDROGEN BONDS; OXIDATION; POLYSACCHARIDES; REDUCTION; THERMAL EFFECTS;

DEPROTONATION; DIMUTASE ACTIVITY; REPROTONATION; TRANSIENT OXIDATIONS;

ENZYMES;

ADENOSINE DIPHOSPHATE; ADENOSINE DIPHOSPHATE BETA DEXTRO MANNOHEXODIALDOSE; ADENOSINE DIPHOSPHATE BETA DEXTRO MANNOSE; ADENOSINE DIPHOSPHATE BETA DEXTRO MANNURONIC ACID; ADENOSINE DIPHOSPHATE LEVO GLYCERO DEXTRO MANNOHEPTOSE 6 EPIMERASE; ALDEHYDE; CARBOHYDRATE DERIVATIVE; EPIMERASE; MANNOSE; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; SUPEROXIDE DISMUTASE; UNCLASSIFIED DRUG;

ARTICLE; BIOLOGICAL MONITORING; CATALYSIS; CATALYST; ENZYME ACTIVITY; INCUBATION TIME; NUCLEOTIDE SEQUENCE; OXIDATION; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; PROTON TRANSPORT; REDUCTION; STEREOCHEMISTRY; STEREOSPECIFICITY; ULTRAVIOLET SPECTROSCOPY;

BASE SEQUENCE; CARBOHYDRATE EPIMERASES; CLONING, MOLECULAR; DNA, BACTERIAL; ESCHERICHIA COLI; MODELS, BIOLOGICAL; NADP; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OXIDATION-REDUCTION; RECOMBINANT PROTEINS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

NEGIBACTERIA;

EID: 17144370967     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi050106c     Document Type: Article

References (33)

1. Raetz, C. R. H., and Whitfield, C. (2002) Lipopolysaccharide endotoxins, Annu. Rev. Biochem. 71, 635-700.
2. Raetz, C. R. H. (1996) in Escherichia coli and Salmonella (Neidhardt, F. C., Ed.) pp 1035-1063, American Society for Microbiology, Washington, DC.
3. Zamyatina, A., Gronow, S., Oertelt, C., Puchberger, M., Brade, H., and Kosma, P. (2000) Efficient chemical synthesis of the two anomers of ADP-L-glycero- and D-glycero-D-manno-hepto-pyranose allows the determination of the substrate specificities of bacterial heptosyltransferases, Angew. Chem., Int. Ed. 39, 4150-4153.
4. Kneidinger, B., Marolda, C., Graninger, M., Zamyatina, A., McArthur, F., Kosma, P., Valvano, M. A., and Messner, P. (2002) Biosynthesis pathway of ADP-L-glycero-β-D-manno-heptose in Escherichia coli, J. Bacteriol. 184, 363-369.
5. Valvano, M. A., Messner, P., and Kosma, P. (2002) Novel pathways for biosynthesis of nucleotide-activated glycero-manno-heptose precursors of bacterial glycoproteins and cell surface polysaccharides, Microbiology 148, 1979-1989.
6. Samuel, J., and Tanner, M. E. (2002) Mechanistic aspects of enzymatic carbohydrate epimerization, Nat. Prod. Rep. 19, 261-277.
7. Tanner, M. E. (2002) Understanding nature's strategies for enzyme-catalyzed racemization and epimerization, Acc. Chem. Res. 35, 237-246.
8. + is the physiological cofactor of ADP-L-glycero-D-manno-heptose 6-epimerase, J. Biol. Chem. 276, 27329-27334.
9. Deacon, A. M., Ni, Y. S., Coleman, W. G., Jr., and Ealick, S. E. (2000) The crystal structure of ADP-L-glycero-D-manno-heptose 6-epimerase: catalysis with a twist, Structure 8, 453-461.
10. Ding, L., Seto, B. L., Ahmed, S. A., and Coleman, W. G., Jr. (1994) Purification and properties of the Escherichia coli K-12 NAD-dependent nucleotide diphosphosugar epimerase, ADP-L-glycero-D-manno-heptose 6-epimerase, J. Biol. Chem. 269, 24384-24390.
11. Read, J. A., Ahmed, R. A., Morrison, J. P., Coleman, W. G., Jr., and Tanner, M. E. (2004) The mechanism of the reaction catalyzed by ADP-β-L-glycero-D-manno-heptose 6-epimerase, J. Am. Chem. Soc. 126, 8878-8879.
12. + and active site residues of UDP-galactose 4-epimerase: Implications for the activation induced by uridine nucleotides, Biochemistry 40, 11279-11287.
13. Berger, E., Arabshahi, A., Wei, Y., Schilling, J. F., and Frey, P. A. (2001) Acid-base catalysis by UDP-galactose 4-epimerase: Correlations of kinetically measured acid dissociation constants with thermodynamic values for tyrosine 149, Biochemistry 40, 6699-6705.
14. Thoden, J. B., and Holden, H. M. (1998) Dramatic differences in the binding of UDP-galactose and UDP-glucose to UDP-galactose 4-epimerase from E. coli, Biochemistry 37, 11469-11477.
15. Frey, P. A. (1996) The Leloir pathway, FASEB J. 10, 461-470.
16. Koropatkin, N. M., Liu, H.-W., and Holden, H. M. (2003) High resolution X-ray structure of tyvelose epimerase from Salmonella typhi, J. Biol. Chem. 278, 20847-20881.
17. Hallis, T. M., Zhao, Z., and Liu, H.-W. (2000) New insights into the mechanism of CDP-tyvelose 2-epimerase: an enzyme catalyzing epimerization at an unactivated stereocenter, J. Am. Chem. Soc. 122, 10493-10503.
18. Bradford, M. M. (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding, Anal. Biochem. 72, 248-254.
19. Helferich, B., and Leete, J. F. (1929) Trityläther der mannose. Eine neue tetracetyl-mannose, Ber. Dtsch. Chem. Ges. 62, 1549-1554.
20. Campbell, R. E., and Tanner, M. E. (1997) Uridine diphospho-α-D- gluco-hexodialdose: Synthesis and kinetic competence in the reaction catalyzed by UDP-glucose dehydrogenase, Angew. Chem., Intl. Ed. Engl. 36, 1520-1522.
21. Nicoll-Griffith, D., and Weiler, L. (1984) Stereospecific introduction of an asymmetric centre at C-6 in a glycoside, J. Chem. Soc., Chem. Commun. 659-661.
22. Binkley, R. W. (1977) A mud process for the oxidation of partially protected carbohydrates, J. Org. Chem. 42, 1216-1221.
23. 4. Applications to gibberellins, Tetrahedron Lett. 23, 4293-4296.
24. Sim, M. M., Kondo, H., and Wong, C.-H. (1993) Synthesis and use of glycosyl phosphites: An effective route to glycosyl phosphates, sugar nucleotides and glycosides, J. Am. Chem. Soc. 115, 2260-2267.
25. Gardner Swain, C., Powell, A. L., Sheppard, W. A., and Morgan, C. R. (1979) Mechanism of the Cannizzaro reaction, J. Am. Chem. Soc. 101, 3576-3583.
26. Ge, X., Penney, L. C., van de Rijn, I., and Tanner, M. E. (2004) Active site residues and mechanism of UDP-glucose dehydrogenase, Eur. J. Biochem. 271, 14-22.
27. Henehan, G. T. M., Chang, S. H., and Oppenheimer, N. J. (1995) Aldehyde dehydrogenase activity of Drosophila melanogaster alcohol dehydrogenase: Burst kinetics at high pH and aldehyde dismutase activity at physiological pH, Biochemistry 34, 12294-12301.
28. Henehan, G. T. M., and Oppenheimer, N. J. (1993) Horse liver alcohol dehydrogenase-catalyzed oxidation of aldehydes: Dismutation precedes net production of reduced nicotiamide adenine dinucleotide, Biochemistry 32, 735-738.
29. Hara, A., Yamamoto, H., Deyashiki, Y., Nakayama, T., Oritani, H., and Sawada, H. (1991) Aldehdye dismutation catalyzed by pulmonary carbonyl reductase: Kinetic studies of chloral hydrate metabolism to trichloroacetic acid and trichloroethanol, Biochim. Biophys. Acta 1075, 61-67.
30. Eisses, K. T. (1989) On the oxidation of aldehdyes by alcohol dehydrogenase of Drosophila melanogaster: Evidence for the gem-diol as the reacting substrate, Bioorg. Chem. 17, 268-274.
31. Moxon, L. N., Holmes, R. S., Parsons, P. A., Irving, M. G., and Doddrell, D. M. (1985) Purification and molecular properties of alcohol dehydrogenase from Drosophila melanogaster: Evidence from NMR and kinetic studies for function as an aldehdye dehydrogenase, Comp. Biochem. Physiol. 80B, 525-535.
32. Hinson, J. A., and Neal, R. A. (1975) An examination of octanol and octanol metabolism to octanoic acid by horse liver alcohol dehydrogenase, Biochim. Biophys. Acta 384, 1-11.
33. Abeles, R. H., and Lee, H. A., Jr. (1960) The dismutation of formaldehyde by liver alcohol dehydrogenase, J. Biol. Chem. 235, 1499-1503.