Si-face stereospecificity at C5 of coenzyme F420 for F420-dependent glucose-6-phosphate dehydrogenase from Mycobacterium smegmatis and f420-dependent alcohol dehydrogenase from Methanoculleus thermophilicus

European Journal of Biochemistry

Volumn 239, Issue 1, 1996, Pages 93-97

  Klein, Andreas R ^a   Berk, Holger ^a   Purwantini, Endang ^b   Daniels, Lacy ^b   Thauer, Rudolf K ^a,c  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b UNIVERSITY OF IOWA   (United States)

^c MAX PLANCK INSTITUTE FOR TERRESTRIAL MICROBIOLOGY   (Germany)

Author keywords

Coenzyme F420; F420 dependent alcohol dehydrogenase; F420 dependent glucose 6 phosphate dehydrogenase; Methanogenic Archaea; Mycobacterium

Indexed keywords

ALCOHOL DEHYDROGENASE; COENZYME F420; GLUCOSE 6 PHOSPHATE DEHYDROGENASE; UNCLASSIFIED DRUG;

ARTICLE; ENZYME ACTIVITY; METHANOBACTERIUM; MYCOBACTERIUM SMEGMATIS; PRIORITY JOURNAL; STEREOSPECIFICITY;

ARCHAEA; METHANOBACTERIUM; METHANOCULLEUS THERMOPHILUS; MYCOBACTERIUM; MYCOBACTERIUM SMEGMATIS; TRITIUM;

EID: 0029984804     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1432-1033.1996.0093u.x     Document Type: Article

References (46)

1. Alex , L. A., Reeve, J. N., Orme-Johnson, W. H. & Walsh, C. T. (1990) Cloning, sequence determination, and expression of the genes encoding the snbunits of the nickel-containing 8-hydroxy-5-deazaflavin reducing hydrogenase from Methanobacterium thermoautotrophicum AH. Biochemistry 29, 7237-7244.
2. Benner, S. A. (1982) The stereoselectivivity of alcohol dehydrogenases: A stereochemical imperative ? Experientia 38, 633-637.
3. Benner, S. A., Nambiar, K. P & Chambers, G. K. (1985) A stereochemical imperative in dehydrogenases: New data and criteria for evaluating function-based therories in bioorganic chemistry, J. Am. Chem. Soc. 107, 5513-5517.
4. Breitung, J., Börner, G., Scholz, S., Linder, D., Stetter, K. O. & Thauer, R. K. (1992) Salt dependence, kinetic properties and catalytic mechanism of N-formylmethanofuran:tetrahydromethanopterin formyltransferase from the extreme thermophile Methanopyrus kandleri, Eur. J. Biochem. 210, 971 - 981.
5. 420. from Methanobacterium strain M.o. H. J. Bacteriol. 112, 527 - 531.
6. Coats, J. H., Li, G. P., Kuo, M.-S. & Yurek, D. A. (1989) Discovery, production, and biological assay of an unusual flavenoid cofactor involved in lincomycin biosynthesis, J. Antibiot. 42, 472 - 474.
7. Daniels, L., Bakhiet, N. & Harmon, K. (1985) Widespread distribution of a 5-deazaflavin cofactor in actinomyces and related bacteria. System. Appl. Microbiol. 6, 12 - 17.
8. DiMarco, A. A., Bobik, T. A. & Wolfe, R. S. (1990) Unusual coenzymes of methanogenesis. Annu. Rev. Biochem. 59, 355 - 394.
9. 420 from Methanobacterium. Biochemistry 17, 4583 - 4593.
10. Eker, A. P. M., Hessels, J. K. C. & van de Velde, J. (1988) Photoreacting enzyme from the green alga Scenedesmus acutus. Evidence for the presence of two different flavin chromophores, Biochemistry 27, 1758 - 1765.
11. Escalante-Semerena, J. C., Rinehart, K. L. Jr & Wolfe, R. S. (1984) Tetrahydromethanopterin, a carbon carrier in methanogenesis, J. Biol. Chem. 259, 9447 - 9455.
12. Fox, J. A., Livingston, D. J., Orme-Johnson, W. H. & Walsh, C. T. (1987) 8-Hydroxy-5-deazaflavin-reducing hydrogenase from Methanobacterium thermoautotrophicum: 1. Purification and characterization. Biochemistry 26, 4219-4227.
13. Glasfeld, A. & Benner, S. A. (1989) The specificity of the ferrous-ion-dependent alcohol dehydrogenase from Zymomonas mobilis, Eur. J. Biochem. 180, 373-375.
14. Gloss, L. M. & Hausinger, R. P. (1987) Reduction potential characterization of methanogen factor 390. FEMS Microbiol. Lett. 48, 143 - 145.
15. Jacobson, F. & Walsh, C. (1984) Properties of 7,8-didemethyl-8-hydroxy-5-deazaflavins relevant to redox coenzyme function in methanogen metabolism, Biochemistry 23, 979 -988.
16. Kiener, A., Husain, I., Sancar, A. & Walsh, C. (1989) Purification and properties of Methanobacterum thermoautotrophicum DNA photolyase, J. Biol. Chem. 264, 13880 - 13887.
17. 2 → T< >T) kinetics in Anacystis nidulans photolyase, Biochemistry 31. 11244 - 11248.
18. 420-dependent methylenetetrahydro-methanopterin dehydrogenase from methanogenic Archaea, Eur. J. Biochem. 227, 169 - 174.
19. 120-dependent enzyme, Arch. Microbiol. 160, 186 - 192.
20. 420-dependent NADP reductase in the extremely thermophilic sulfate reducing Archacoglobus fulgidus, Arch. Microbiol. 160, 199 - 205.
21. 2:dimethylnaphthoquinone oxidoreductase, Eur. J. Biochem. 214, 641 - 646.
22. Kuo, M.-S., Yurek, D. A., Coats, J. H. & Li, G. P. (1989) Isolation and identification of 7,8-didemethyl-8-hydroxy-5-deazariboflavin, an unusual cosynthetic factor in Streptomycetes,from Streptomyces lincolncnsis, J. Antibiot. 3, 475 - 479.
23. 420 and its γ-monoglutamyl derivative in nonmethanogenic archaebacteria. J. Bacteriol. 168, 444 - 448.
24. Mayerl, F., Piret, J., Kiener, A., Walsh, C. T. & Yasui, A. (1990) Functional expression of 5-deazaflavin dependent DNA photolyase from Anacystis nidulans in Streptomyces dependent DNA photolyase from 6061 - 6065.
25. 420 of Methanobacteriun species. J. Am. Chem. Soc. 104, 4014 - 4015.
26. 420 in Archaeoglobus fulgidus, Arch. Microbiol. 152, 362 - 368.
27. 420-dependent methylene-5,6,7,8-tetrahydromethanopterin dehydrogenase gene from Methanobacterium thermoautotrophicum strain Marburg and functional expression in Escherichia coli, J. Biol. Chem. 270, 2827 - 2832.
28. Piepersberg, W. (1994) Pathway engineering in secondary metabolite-producing actinomycetes. Crit. Rev. Biotechnol. 14, 251 - 285.
29. 420-dependent glucose-6-phosphate dehydrogenase from Mycobacterium smegmatis, J. Bacteriol. 178, 2861 - 2866.
30. Sancar, G. B. & Sancar, A. (1987) Structure and function of DNA photolyases, Trends Biochem. Sci. 12, 259 - 261.
31. 420 reducing formate dehydrogenase from Methanobacteriun formicicum, Biochemistry 25, 7163 - 7168.
32. 10-methylenetetrahydromethanopterin dehydrogenase from Methanobacterium thermoautotrophicum catalyzes a stereo-selective hydride transfer as determined by two-dimensional NMR spectroscopy, Biochemistry 33, 3986 - 3993.
33. x) of Methanobacterium themoautotrophicum, Arch. Microbiol. 127, 59 - 65.
34. Shuher, A. P., Orr, E. C., Recny, M. A., Schendel, P. F., May, H. D., Schauer, N. L. & Ferry, J. G. (1986) Cloning, expression, and nucleotide sequence of the formate dehydrogenase genes from Methanobacterium formicicum, J. Biol. Chem. 261, 12942 - 12947.
35. Sumner, J. S. & Matthews, R. G. (1992) Stereochemistry and mechanism of hydrogen transfer between NADPH and methylenetetrahydrofolate in the reaction catalyzed by methylenetetrahydrofolate reductase from pig liver, J. Am. Chem. Soc. 114, 6949 - 6956.
36. Takao, M., Kobayashi, T., Oikawa, A. & Yasui, A. (1989) Tandem arrangement of photolyase and Superoxide dismutase genes in Halobacterium halobium, J. Bacteriol. 171, 6323 - 6329.
37. 1]-3,4-dihydro-7-hydroxy-1-hydroxyethylquinolinone. Tetrahedron Lett. 26, 351 - 354
38. 10-methylenetetrahydromethanopterin reductase (Mer) from Methano-bacterium thermoautotrophicum strain Marburg. Cloning. sequencing, transcriptional analysis and functional expression in Escherichia coli of the mer gene, Eur. J. Biochem. 231, 773 - 778.
39. Walsh. C. (1986) Naturally occurring 5-deazaflavin coenzymes: Biological redox roles, Acc. Chem. Res. 19, 216 - 221.
40. Weiss. D. S. & Thauer, R. K. (1993) Methanogenesis and the unity of biochemistry, Cell 72, 819 - 822.
41. 420-specific enzyme from Methanogenium thermophilum strain TCI. Arch. Microbiol. 152, 322 - 328.
42. Wolfe, R. S. (1991) My kind of biology. Annu. Rev. Microbiol. 45, 1 - 35.
43. Yamazaki, S., Tsai, L., Stadtman, T. C., Jacobson, F. S. & Walsh, C. (1980) Stereochemical studies of 8-hydroxy-5-deazaflavin in-dependent NADP reductase from Methanococcus vannielii. J. Biol. Chem. 255, 9025 - 9027.
44. Yamazaki, S., Tsai, L., Stadtman, T. C., Teshima, T., Nakaji, A. & Shiba, T. (1985) Stereochemical studies of a selenium-containing hydrogenase from Methanococcus vannielii: Determination of the absolute configuration of C-5 chirally labeled dihydro-8-hydroxy-5-deazaflavin cofactor, Proc. Natl Acad. Sci. USA 82, 1364 - 1366.
45. Yasui, A., Eker, A. P. M., Yasuhira, S., Yajima, H., Kobayashi, T., Takao, M. & Oikawa, A. (1994) A new class of DNA photolyases in various organisms including aplacental mammals, EMBO J. 13, 6143 - 6151.
46. You, K. (1982) Stereospecificities of the pyridine nucleotide-linked enzymes, Methods Enzymol. 87, 101 - 126.