Flavin adenine dinucleotide-dependent 4-phospho-D-erythronate dehydrogenase is responsible for the 4-phosphohydroxy-L-threonine pathway in vitamin B 6 biosynthesis in Sinorhizobium meliloti

Journal of Bacteriology

Volumn 188, Issue 13, 2006, Pages 4635-4645

  Tazoe, Masaaki ^a,b   Ichikawa, Keiko ^a,c   Hoshino, Tatsuo ^a,b  

^a NIPPON ROCHE RESEARCH CENTER   (Japan)

^b TAMAGAWA UNIVERSITY   (Japan)

^c CHUGAI PHARMACEUTICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXOBUTYRIC ACID; 3 HYDROXY 4 PHOSPHOHYDROXY ALPHA KETOBUTYRATE; 4 PHOSPHOHYDROXYTHREONINE; ALDEHYDE; CARBON 13; FLAVINE ADENINE NUCLEOTIDE; FLAVINE ADENINE NUCLEOTIDE DEPENDENT 4 PHOSPHO DEXTRO ERYTHRONATE DEHYDROGENASE; GENE PRODUCT; GLYCINE; GLYCOALDEHYDE; ISOMERASE; NICOTINAMIDE ADENINE DINUCLEOTIDE; OXIDOREDUCTASE; PHOSPHOTRANSFERASE; PYRIDOXINE; THREONINE; TRANSKETOLASE; UNCLASSIFIED DRUG;

ARTICLE; AUXOTROPHY; BACTERIAL GENE; BIOSYNTHESIS; CARBOHYDRATE METABOLISM; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DNA SEQUENCE; ESCHERICHIA COLI K 12; MOLECULAR CLONING; NONHUMAN; NUCLEOTIDE SEQUENCE; OXIDATION; PDXB GENE; PDXR GENE; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; POLYMERASE CHAIN REACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SACCHAROMYCES CARLSBERGENSIS; SINORHIZOBIUM MELILOTI;

ACETALDEHYDE; AMINO ACID SEQUENCE; BACTERIAL PROTEINS; FLAVIN-ADENINE DINUCLEOTIDE; GENES, BACTERIAL; ISOMERASES; MOLECULAR SEQUENCE DATA; OPEN READING FRAMES; OXIDATION-REDUCTION; OXIDOREDUCTASES; PHOSPHORIC ACID ESTERS; PHOSPHOTRANSFERASES; SEQUENCE ALIGNMENT; SINORHIZOBIUM MELILOTI; THREONINE; TRANSKETOLASE; VITAMIN B 6;

ESCHERICHIA COLI K12; SINORHIZOBIUM MELILOTI;

EID: 33745444610     PISSN: 00219193     EISSN: None     Source Type: Journal    
DOI: 10.1128/JB.01999-05     Document Type: Article

References (49)

1. Bandurski, R. S., and B. Axelrod. 1951. The Chromatographic identification of some biologically important phosphate esters. J. Biol. Chem. 193:405-410.
2. Burns, K. E., Y. Xiang, C. L. Kinsland, F. W. McLafferty, and T. P. Begley. 2005. Reconstitution and biochemical characterization of a new pyridoxal-5′-phosphate biosynthetic pathway. J. Am. Chem. Soc. 127:3682-3683.
3. Cammack, R. 1968. Flavoprotein properties of D-2-hydroxyacid dehydrogenase purified from rabbit kidney. Biochem. J. 109:45-46.
4. Cane, D. E., S. Du, J. K. Robinson, Y. Hsiung, and I. D. Spenser. 1999. Biosynthesis of vitamin B6: enzymatic conversion of 1-deoxy-D-xylulose-5- phosphate to pyridoxol phosphate. J. Am. Chem. Soc. 121:7722-7723.
5. Capela, D., F. Barloy-Hubler, J. Gouzy, G. Bothe, F. Ampe, J. Batut, P. Boistard, A. Becker, M. Boutry, E. Cadieu, S. Dréano, S. Gloux, T. Godrie, A. Goffeau, D. Kahn, E. Kiss, V. Lelaure, D. Masuy, T. Pohl, D. Porteteile, A. Fühler, B. Purnelle, U. Ramsperger, C. Renard, P. Thébault, M. Vandenbol, S. Weidner, and F. Galibert. 2001. Analysis of the chromosome sequence of the legume symbiont Sinorhizobium meliloti strain 1021. Proc. Natl. Acad. Sci. USA 98:9877-9882.
6. De Lajudie, P., A. Willems, B. Pot, D. Dewettinck, G. Maestrojuan, M. Neyra, M. D. Collins, B. Dreyfus, K. Kersters, and M. Gillis. 1994. Polyphasic taxonomy of rhizobia: emendation of the genus Sinorhizobium and description of Sinorhizobium meliloti comb. nov., Sinorhizobium saheli sp. nov., and Sinorhizobium teranga sp. nov. Int. J. Syst. Bacteriol. 44:715-733.
7. Dempsey, W. B. 1987. Synthesis of pyridoxal phosphate, p. 539-543. In F. C. Neidhardt, J. L. Ingraham, K. B. Low, B. Magasanik, M. Schaechter, and H. E. Umbarger (ed.), Escherichia coli and Salmonella typhimurium: cellular and molecular biology, vol. 1. American Society for Microbiology, Washington, D.C.
8. Dempsey, W. B. 1969. Characterization of pyridoxine auxotrophs of Escherichia coli: chromosomal position of linkage group I. J. Bacteriol. 100:295-300.
9. 6 biosynthesis. FEBS Lett. 390:179-182.
10. Ebner, M., and A. E. Stütz. 1997. Glucose isomerase catalysed isomerisation reactions of (2R,3R)-configured aldofuranoses into the corresponding open-chain 2-ketoses. Carbohydr. Res. 305:331-336.
11. 6 biosynthesis. Proc. Natl. Acad. Sci. USA 96:9374-9378.
12. Ehrenshaft, M., and M. E. Daub. 2001. Isolation of PDX2, a second novel gene in the pyridoxine biosynthesis pathway of eukaryotes, archaebacteria, and a subset of eubacteria. J. Bacteriol. 183:3383-3390.
13. Elkan, G. H., and C. R. Bunn. 1994. The rhizobia, p. 2197-2213. In A. Balows, H. G. Trüper, M. Dworkin, W. Harder, and K. H. Schleifer (ed.), The prokaryotes, 2nd ed., vol. 3. Springer-Verlag, New York, N.Y.
14. Farrington, G. K., A. Kumar, S. L. Shames, J. I. Ewaskiewicz, D. E. Ash, and F. C. Wedler. 1993. Threonine synthase of Escherichia coli: inhibition by classical and slow-binding analogues of homoserine phosphate. Arch. Biochem. Biophys. 307:165-174.
15. Galibert, F., T. M. Finan, S. R. Long, A. Pühler, P. Abola, F. Ampe, F. Barloy-Hubler, M. J. Barnett, A. Becker, P. Boistard, G. Bothe, M. Boutry, L. Bowser, J. Buhrmester, E. Cadieu, D. Capela, P. Chain, A. Cowie, R. W. Davis, S. Dréano, N. A. Federspiel, R. F. Fisher, S. Gloux, T. Godrie, A. Goffeau, B. Golding, J. Gouzy, M. Gurjal, I. Hernandez-Lucas, A. Hong, L. Huizar, R. W. Hyman, T. Jones, D. Kahn, M. L. Kahn, S. Kalman, D. H. Keating, E. Kiss, C. Komp, V. Lelaure, D. Masuy, C. Palm, M. C. Peck, T. M. Pohl, D. Portetelle, B. Purnelle, U. Ramsperger, R. Surzycki, P. Thébault, M. Vandenbol, F.-J. Vörholter, S. Weidner, D. H. Wells, K. Wong, K.-C. Yeh, and J. Batut. 2001. The composite genome of the legume symbiont Sinorhizobium zobium meliloti. Science 293:668-672.
16. Glazebrook, J., and G. C. Walker. 1991. Genetic techniques in Rhizobium meliloti. Methods Enzymol. 204:398-418.
17. Hanes, C. S., and F. A. Ishenvood. 1949. Separation of the phosphoric esters on the filter paper chromatogram. Nature 164:1107-1112.
18. 6. J. Biol. Chem. 271:30426-30435.
19. 6, p. 695-703. In F. C. Neidhardt, R. Curtiss III, J. L. Ingraham, E. C. C. Lin, K. B. Low, B. Magasanik, W. S. Reznikoff, M. Riley, M. Schaechter, and H. E. Umbarger (ed.), Escherichia coli and Salmonella: cellular and molecular biology, 2nd ed., vol. 1. American Society for Microbiology, Washington, D.C.
20. Hoshino, T., Y. Nagatani, K. Ichikawa, and M. Tazoe. April 2004. W.O. patent 029270 A2.
21. Kennedy, I. A., R. E. Hill, R. M. Pauloski, B. G. Sayer, and I. D. Spenser. 1995. Biosynthesis of vitamin B6: origin of pyridoxine by the union of two acyclic precursors, 1-deoxy-D-xylulose and 4-hydroxy-L-threonine. J. Am. Chem. Soc. 117:1661-1662.
22. Knauf, V. C., and E. W. Nester. 1982. Wide host range cloning vectors: a cosmid clone bank of an Agrobacterium Ti plasmid. Plasmid 8:45-54.
23. 6 biosynthesis: formation of pyridoxine 5′-phosphate from 4-(phosphohy-droxy)-L-threonine and 1-deoxy-D-xylulose-5-phosphate by PdxA and PdxJ protein. FEBS Lett. 449:45-48.
24. Laemmli, U. K. 1970. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227:680-685.
25. Lam, H.-M., and M. E. Winkler. 1990. Metabolic relationships between pyridoxine (vitamin B6) and serine biosynthesis in Escherichia coli K-12. J. Bacteriol. 172:6518-6528.
26. Lowry, O. H., N. J. Rosebrough, A. L. Farr, and R. J. Randall. 1951. Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193:265-275.
27. Marchler-Bauer, A., J. B. Anderson, C. DeWeese-Scott, N. D. Fedorova, L. Y. Geer, S. He, D. I. Hurwitz, J. D. Jackson, A. R. Jacobs, C. J. Lanczycki, C. A. Liebert, C. Liu, T. Madej, G. H. Marchler, R. Mazumder, A. N. Nikolskaya, A. R. Panchenko, B. S. Rao, B. A. Shoemaker, V. Simonyan, J. S. Song, P. A. Thiessen, S. Vasudevan, Y. Wang, R. A. Yamashita, J. J. Yin, and S. H. Bryant. 2003. CDD: a curated Entrez database of conserved domain alignments. Nucleic Acids Res. 31:383-387.
28. Mitchell, R. E., E. J. Frey, and M. H. Benn. 1986. Rhizobitoxine and L-threo-hydroxythreonine production by the plant pathogen Pseudomonas andropogonis. Phytochemistry 25:2711-2715.
29. Murray, N. E., W. J. Brammar, and K. Murray. 1977, Lambdoid phages that simplify the recovery of in vitro recombinants. Mol. Gen. Genet. 150:53-61.
30. Osmani, A. H., G. S. May, and S. A. Osmani. 1999. The extremely conserved pyroA gene of Aspergillus nidulans is required for pyridoxine synthesis and is required indirectly for resistance to photosensitizers. J. Biol. Chem. 274:23565-23569.
31. Pizer, L. I. 1963. The pathway and control of serine biosynthesis in Escherichia coli. J. Biol. Chem. 238:3934-3944.
32. Rohmer, M., M. Knani, P. Simonin, B. Sutler, and H. Sahm. 1993. Isoprenoid biosynthesis in bacteria: a novel pathway for the early steps leading to isopentenyl diphosphate. Biochem. J. 295:517-524.
33. Schoenlein, P. V., B. B. Roa, and M. E. Winkler. 1989. Divergent transcription of pdxB and homology between the pdxB and serA gene products in Escherichia coli K-12. J. Bacteriol. 171:6084-6092.
34. Sevostyanova, I. A., O. N. Soloyjeva, and G. A. Kochetov. 2004. A hitherto unknown transketolase-catalyzed reaction. Biochem. Biophys. Res. Commun. 313:771-774.
35. Shames, S. L., D. E. Ash, F. C. Wedler, and J. J. Villafranca. 1984. Interaction aspartate and aspartate-derived antimetabolites with the enzymes of the threonine biosynthetic pathway of Escherichia coli. J. Biol. Chem. 259:15331-15339.
36. Simon, R., U. Priefer, and A. Pühler. 1983. A broad host range mobilization system for in vivo genetic engineering: transposon mutagenesis in gram negative bacteria. Bio/Technology 1:784-791.
37. Sperry, J. F., and D. C. Robertson. 1975. Erythritol catabolism by Brucella abortus. J. Bacteriol. 121:619-630.
38. 6 in Rhizobium. J. Biol. Chem. 275:11300-11305.
39. 6 in Rhizobium: in vitro synthesis of pyridoxine from 1-deoxy-D-xylulose and 4-hydroxy-L-threonine. Biosci. Biotechnol. Biochem. 66:934-936.
40. Tazoe, M., K. Ichikawa, and T. Hoshino. Unpublished results.
41. Tazoe, M., K. Ichikawa, and T. Hoshino. 2005. Purification and characterization of pyridoxine 5′-phosphate phosphatase from Sinorhizobium meliloti. Biosci. Biotechnol. Biochem. 69:2277-2284.
42. 6 in Rhizobium. Biosci. Biotechnol. Biochem. 63:1378-1382.
43. Thérisod, M., J. C. Fischer, and B. Estramareix. 1981. The origin of the carbon chain in the thiazole moiety of thiamine in Escherichia coli: incorporation of deuterated 1-deoxy-D-threo-2-pentulose. Biochem. Biophys. Res. Commun. 98:374-379.
44. Wawszkiewicz, E. J., and H. A. Barker. 1968. Erythritol metabolism by Propionibacterium pentosaceum. J. Biol. Chem. 243:1948-1956.
45. Woodruff, W. W., III, and R. Wolfenden. 1979. Inhibition of ribose-5-phosphate isomerase by 4-phosphoerythronate. J. Biol. Chem. 254:5866-5867.
46. Wungsintaweekul, J., S. Herz, S. Hecht, W. Wisenreich, R. Feicht, F. Rohdich, A. Bacher, and M. H. Zenk. 2001. Phosphorylation of 1-deoxy-D-xylulose by D-xylulokinase of Escherichia coli. Eur. J. Biochem. 268:310-316.
47. Yang, Y., G. Zhao, T.-K. Man, and M. E. Winkler. 1998. Involvement of the gapA- and epd (gapB)-encoded dehydrogenases in pyridoxal 5′-phosphate coenzyme biosynthesis in Escherichia coli K-12. J. Bacteriol. 180:4294-4299.
48. Yokota, A., and K. Sasajima. 1984. Formation of 1-deoxy-D-threo-pentulose and 1-deoxy-L-rAreo-pentulose by cell-free extracts of microorganisms. Agric. Biol. Chem. 48:149-158.
49. Zhao, G., A. J. Pease, N. Bharani, and M. E. Winkler. 1995. Biochemical characterization of gapB-encoded erythrose 4-phosphate dehydrogenase of Escherichia coli K-12 and its possible role in pyridoxal 5′-phosphate biosynthesis. J. Bacteriol. 177:2804-2812.