‘New uses for an Old Enzyme’ – the Old Yellow Enzyme family of flavoenzymes

References

1. Abramovitz A. S., Massey V. 1976; Interaction of phenols with Old Yellow Enzyme. Physical evidence for charge-transfer complexes. J Biol Chem 251:5327–5336
   [Google Scholar]
2. Altamirano M. M., Blackburn J. M., Aguayo C., Fersht A. R. 2000; Directed evolution of new catalytic activity using the α/β-barrel scaffold. Nature 403:617–622 [CrossRef]
   [Google Scholar]
3. Amberg D. C., Basart E., Botstein D. 1995; Defining protein interactions with yeast actin in vivo. Nat Struct Biol 2:28–35 [CrossRef]
   [Google Scholar]
4. Barna T. M., Khan H., Bruce N. C., Barsukov I., Scrutton N. S., Moody P. C. 2001; Crystal structure of pentaerythritol tetranitrate reductase: ‘‘flipped’’ binding geometries for steroid substrates in different redox states of the enzyme. J Mol Biol 310:433–447 [CrossRef]
   [Google Scholar]
5. Binks P. R., French C. E., Nicklin S., Bruce N. C. 1996; Degradation of pentaerythritol tetranitrate by Enterobacter cloacae PB2. Appl Environ Microbiol 62:1214–1219
   [Google Scholar]
6. Blehert D. S., Fox B. G., Chambliss G. H. 1999; Cloning and sequence analysis of two Pseudomonas flavoprotein xenobiotic reductases. J Bacteriol 181:6254–6263
   [Google Scholar]
7. Boonstra B., Rathbone D. A., Bruce N. C. 2001; Engineering novel biocatalytic routes for production of semisynthetic opiate drugs. Biomol Eng 18:41–47 [CrossRef]
   [Google Scholar]
8. Breithaupt C., Strassner J., Breitinger U., Huber R., Macheroux P., Schaller A., Clausen T. 2001; X-ray structure of 12-oxophytodienoate reductase 1 provides structural insight into substrate binding and specificity within the family of OYE. Structure 9:419–429 [CrossRef]
   [Google Scholar]
9. Brown B. J., Massey V. 1999; Study of the function of Old Yellow Enzyme in Saccharomyces cerevisiae . In Flavins and Flavoproteins 1999; Proceedings of the Thirteenth International Symposium pp 659–662 Edited by Ghisla S., Kroneck P., Macheroux P., Sund H. Berlin: Walter de Gruyter;
   [Google Scholar]
10. Brown B. J., Deng Z., Karplus P. A., Massey V. 1998; On the active site of Old Yellow Enzyme – role of histidine 191 and asparagine 194. J Biol Chem 273:32753–32762 [CrossRef]
    [Google Scholar]
11. Buckman J., Miller S. M. 2000; Transient kinetics and intermediates formed during the electron transfer reaction catalyzed by Candida albicans estrogen binding protein. Biochemistry 39:10521–10531 [CrossRef]
    [Google Scholar]
12. Falzon L., Davidson V. L. 1996; Intramolecular electron transfer in trimethylamine dehydrogenase: a thermodynamic analysis. Biochemistry 35:12111–12118 [CrossRef]
    [Google Scholar]
13. Farmer E. E. 2001; Surface-to-air signals. Nature 411:854–856 [CrossRef]
    [Google Scholar]
14. Fox K. M., Karplus P. A. 1994; Old Yellow Enzyme at 2 Å resolution – overall structure, ligand-binding, and comparison with related flavoproteins. Structure 2:1089–1105 [CrossRef]
    [Google Scholar]
15. French C. E., Bruce N. C. 1994; Purification and characterization of morphinone reductase from Pseudomonas putida M10. Biochem J 301:97–103
    [Google Scholar]
16. French C. E., Nicklin S., Bruce N. C. 1998; Aerobic degradation of 2,4,6-trinitrotoluene by Enterobacter cloacae PB2 and by pentaerythritol tetranitrate reductase. Appl Environ Microbiol 64:2864–2868
    [Google Scholar]
17. French C. E., Rosser S. J., Davies G. J., Nicklin S., Bruce N. C. 1999; Biodegradation of explosives by transgenic plants expressing pentaerythritol tetranitrate reductase. Nat Biotechnol 17:491–494 [CrossRef]
    [Google Scholar]
18. Haas E. 1938; Isolierung eines neuen gelben Ferments. Biochem Z 298:378–390
    [Google Scholar]
19. Hailes A. M., Bruce N. C. 1993; Biological synthesis of the analgesic hydromorphone, an intermediate in the metabolism of morphine, by Pseudomonas putida M10. Appl Environ Microbiol 59:2166–2170
    [Google Scholar]
20. He X. Y., Yang S. Y., Schulz H. 1997; Cloning and expression of the fad H gene and characterization of the gene product 2,4-dienoyl-coenzyme A reductase from Escherichia coli . Eur J Biochem 248:516–520 [CrossRef]
    [Google Scholar]
21. Iuchi S., Yamaguchishinozaki K., Urao T., Terao T., Shinozaki K. 1996; Novel drought-inducible genes in the highly drought-tolerant cowpea – cloning of cDNAs and analysis of the expression of the corresponding genes. Plant Cell Physiol 37:1073–1082 [CrossRef]
    [Google Scholar]
22. Kohli R. M., Massey V. 1998; The oxidative half-reaction of old yellow enzyme – the role of tyrosine 196. J Biol Chem 273:32763–32770 [CrossRef]
    [Google Scholar]
23. Kraulis P. J. 1991; molscript: a program to produce both detailed and schematic plots of protein structure. J Appl Crystallogr 24:946–949 [CrossRef]
    [Google Scholar]
24. Lee J., Godon C., Lagniel G., Spector D., Garin J., Labarre J., Toledano M. B. 1999; Yap1 and Skn7 control two specialized oxidative stress response regulons in yeast. J Biol Chem 274:16040–16046 [CrossRef]
    [Google Scholar]
25. Lim L. W., Shamala N., Mathews F. S., Steenkamp D. J., Hamlin R., Xuong N. H. 1986; Three-dimensional structure of the iron-sulfur flavoprotein trimethylamine dehydrogenase at 2·4 Å resolution. J Biol Chem 261:15140–15146
    [Google Scholar]
26. Massey V., Strickland S., Mayhew S. G., Howell L. G., Engel P. C., Matthews R. G., Schuman M., Sullivan P. A. 1969; The production of superoxide anion radicals in the reaction of reduced flavins and flavoproteins with molecular oxygen. Biochem Biophys Res Commun 36:891–897 [CrossRef]
    [Google Scholar]
27. Meah Y., Massey V. 2000; Old Yellow Enzyme: stepwise reduction of nitro-olefins and catalysis of aci-tautomerisation. Proc Natl Acad Sci USA 97:10733–10738 [CrossRef]
    [Google Scholar]
28. Meah Y., Brown B. J., Chakraborty S., Massey V. 2001; Old Yellow Enzyme: reduction of nitrate esters, glycerin trinitrate, and propylene 1,2-dinitrate. Proc Natl Acad Sci USA 98:8560–8565 [CrossRef]
    [Google Scholar]
29. Miranda M., Ramirez J., Guevara S., Ongaylarios L., Pena A., Coria R. 1995; Nucleotide sequence and chromosomal localization of the gene encoding the Old Yellow Enzyme from Kluyveromyces lactis . Yeast 11:459–465 [CrossRef]
    [Google Scholar]
30. Miura K., Tomioka Y., Suzuki H., Yonezawa M., Hishinuma T., Mizugaki M. 1997; Molecular cloning of the nem A gene encoding N-ethylmaleimide reductase from Escherichia coli . Biol Pharm Bull 20:110–112 [CrossRef]
    [Google Scholar]
31. Mizugaki M., Unuma T., Yamanaka H. 1979; Studies on the metabolism of unsaturated fatty acids. II. Separation and general properties of reduced nicotinamide adenine dinucleotide phosphate dependent cis-2-enoyl-coenzyme A reductase from Escherichia coli K-12. Chem Pharm Bull 27:2334–2337 [CrossRef]
    [Google Scholar]
32. Moody P. C. E., Craig D. H., Scrutton N. S., Munro A. W., Chapman S. K., Bruce N. C. 1999; Structure and mechanism of an opiate-transforming redox enzyme: morphinone reductase. In Flavins and Flavoproteins 1999; Proceedings of the Thirteenth International Symposium pp 667–670 Edited by Ghisla S., Kroneck P., Macheroux P., Sund H. Berlin: Walter de Gruyter;
    [Google Scholar]
33. Murthy Y. V. S. N., Meah Y., Massey V. 1999; Conversion of a flavoprotein reductase to a desaturase by manipulation of the flavin redox potential. J Am Chem Soc 121:5344–5345 [CrossRef]
    [Google Scholar]
34. Niino Y. S., Chakraborty S., Brown B. J., Massey V. 1995; A new old yellow enzyme of Saccharomyces cerevisiae . J Biol Chem 270:1983–1991 [CrossRef]
    [Google Scholar]
35. Peters W., Vanderknaap E., Kende H. 1996; The level of a mRNA with sequence similarity to the Old Yellow Enzyme-NADPH dehydrogenase increases in Chenopodium rubrum cells in response to cytokinin. J Plant Physiol 149:233–236 [CrossRef]
    [Google Scholar]
36. Rathbone D. A., Lister D. L., Bruce N. C. 2001; Biotransformation of alkaloids. Alkaloids Chem Biol 57:1–74
    [Google Scholar]
37. Rohde B. H., Schmid R., Ullrich M. S. 1999; Thermoregulated expression and characterization of an NAD(P)H-dependent 2-cyclohexen-1-one reductase in the plant pathogenic bacterium Pseudomonas syringae pv glycinea. J Bacteriol 181:814–822
    [Google Scholar]
38. Rohdich F., Wiese A., Feicht R., Simon H., Bacher A. 2001; Enoate reductases of Clostridia – cloning, sequencing, and expression. J Biol Chem 276:5779–5787 [CrossRef]
    [Google Scholar]
39. Saito K., Thiele D. J., Davio M., Lockridge O., Massey V. 1991; The cloning and expression of a gene encoding old yellow enzyme from Saccharomyces carlsbergensis . J Biol Chem 266:20720–20724
    [Google Scholar]
40. Schaller F., Weiler E. W. 1997; Molecular cloning and characterization of 12-oxophytodienoate reductase, an enzyme of the octadecanoid signaling pathway from Arabidopsis thaliana . J Biol Chem 272:28066–28072 [CrossRef]
    [Google Scholar]
41. Schaller F., Biesgen C., Mussig C., Altmann T., Weiler E. W. 2000; 12-Oxophytodienoate reductase 3 (OPR3) is the isoenzyme involved in jasmonate biosynthesis. Planta 210:979–984 [CrossRef]
    [Google Scholar]
42. Schopfer L. M., Massey V. 1991; Old Yellow Enzyme. In A Study of Enzymes pp 247–269 Edited by Kuby S. A. Cleveland, OH: CRC Press;
    [Google Scholar]
43. Schuhle K., Jahn M., Ghisla S., Fuchs G. 2001; Two similar gene clusters coding for enzymes of a new type of aerobic 2-aminobenzoate (anthranilate) metabolism in the bacterium Azoarcus evansii . J Bacteriol 183:5268–5278 [CrossRef]
    [Google Scholar]
44. Scrutton N. S. 1994; α/β barrel evolution and the modular assembly of enzymes – emerging trends in the flavin oxidase/dehydrogenase family. Bioessays 16:115–122 [CrossRef]
    [Google Scholar]
45. Snape J. R., Walkley N. A., Morby A. P., Nicklin S., White G. F. 1997; Purification, properties and sequence of glycerol trinitrate reductase from Agrobacterium radiobacter . J Bacteriol 179:7796–7802
    [Google Scholar]
46. Stott K., Saito K., Thiele D. J., Massey V. 1993; Old Yellow Enzyme – the discovery of multiple isozymes and a family of related proteins. J Biol Chem 268:6097–6106
    [Google Scholar]
47. Strassner J., Furholz A., Macheroux P., Amrhein N., Schaller A. 1999; A homolog of Old Yellow Enzyme in tomato – spectral properties and substrate specificity of the recombinant protein. J Biol Chem 274:35067–35073 [CrossRef]
    [Google Scholar]
48. Theorell H. 1955; Nobel Prize Lecture. http://www.nobel.se/medicine/laureates/1955/theorell-lecture.pdf
49. Vaz A. N., Chakraborty S., Massey V. 1995; Old Yellow Enzyme – aromatization of cyclic enones and the mechanism of a novel dismutation reaction. Biochemistry 34:4246–4256 [CrossRef]
    [Google Scholar]
50. Vollenweider S., Weber H., Stolz S., Chetelat A., Farmer E. E. 2000; Fatty acid ketodienes and fatty acid ketotrienes: Michael addition acceptors that accumulate in wounded and diseased Arabidopsis leaves. Plant J 24:467–476 [CrossRef]
    [Google Scholar]
51. Vorbeck C., Lenke H., Fischer P., Spain J. C., Knackmuss H.-J. 1998; Initial reductive reactions in aerobic microbial metabolism of 2,4,6-trinitrotoluene. Appl Environ Microbiol 64:246–252
    [Google Scholar]
52. Warburg O., Christian W. 1932; Ein zweites sauerstoffübertragendes Ferment und sein Absorptionspektrum. Naturwissenschaften 20:688
    [Google Scholar]
53. Wood V., Gwilliam R., Rajandream M. A. 129 other authors 2002; The genome sequence of Schizosaccharomyces pombe . Nature 415:871–880 [CrossRef]
    [Google Scholar]
54. Xu D., Kohli R. M., Massey V. 1999; The role of threonine 37 in flavin reactivity of the Old Yellow Enzyme. Proc Natl Acad Sci USA 96:3556–3561 [CrossRef]
    [Google Scholar]