Characterization of novel 2-oxoglutarate dependent dioxygenases converting l-proline to cis-4-hydroxy-l-proline

Biochemical and Biophysical Research Communications

Volumn 379, Issue 4, 2009, Pages 882-886

  Hara, Ryotaro ^a   Kino, Kuniki ^a  

^a WASEDA UNIVERSITY   (Japan)

Author keywords

2 Oxoglutarate dependent dioxygenase; cis 4 Hydroxy l proline; Hydroxyproline; l Proline cis 4 hydroxylase; Mesorhizobium loti; Proline hydroxylase; Sinorhizobium meliloti

Indexed keywords

2 OXOGLUTARIC ACID; BACTERIAL PROTEIN; DIOXYGENASE; FERROUS ION; HYDROXYPROLINE; OXYGENASE; PROCOLLAGEN PROLINE 2 OXOGLUTARATE 4 DIOXYGENASE; PROLINE;

AMINO ACID SEQUENCE; ARTICLE; ENZYME ACTIVITY; ENZYME ANALYSIS; ESCHERICHIA COLI; MESORHIZOBIUM; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN FUNCTION; PROTEIN PURIFICATION; SEQUENCE HOMOLOGY; SINORHIZOBIUM MELILOTI;

ALPHAPROTEOBACTERIA; CLONING, MOLECULAR; ESCHERICHIA COLI; HYDROGEN-ION CONCENTRATION; HYDROXYPROLINE; KETOGLUTARATE DEHYDROGENASE COMPLEX; PROLINE; SINORHIZOBIUM MELILOTI; TEMPERATURE;

ESCHERICHIA COLI; MESORHIZOBIUM LOTI; SINORHIZOBIUM MELILOTI;

EID: 58949102773     PISSN: 0006291X     EISSN: 10902104     Source Type: Journal    
DOI: 10.1016/j.bbrc.2008.12.158     Document Type: Article

References (26)

1. Sheehan J.C., Zachau H.G., and Lawson W.B. The structure of etamycin. J. Am. Chem. Soc. 79 (1957) 3933-3934
2. Koehn F.E., Longley R.E., and Reed J.K. Microcolins A and B, new immunosuppressive peptides from the blue-green alga Lyngbya majuscula. J. Nat. Prod. 55 (1992) 613-619
3. Irreverre F., Morita K., Ishii S., and Witkop B. Occurrence of cis- and trans-3-hydroxy-l-proline in acid hydrolyzate of telomycin. Biochem. Biophys. Res. Commun. 9 (1962) 69-71
4. Shibata T., Iino K., and Sugimura Y. Synthesis of optically-active 3-mercaptopyrrolidine derivatives, synthetic intermediates of carbapenem rs-533 and its isomer. Heterocycles 24 (1986) 1331-1346
5. Remuzon P. Trans-4-hydroxy-l-proline, a useful and versatile chiral starting block. Tetrahedron 52 (1996) 13803-13835
6. Lawrence C.C., Sobey W.J., Field R.A., Baldwin J.E., and Schofield C.J. Purification and initial characterization of proline 4-hydroxylase from Streptomyces griseoviridus P8648: a 2-oxoacid, ferrous-dependent dioxygenase involved in etamycin biosynthesis. Biochem. J. 313 (1996) 185-191
7. Mori H., Shibasaki T., Yano K., and Ozaki A. Purification and cloning of a proline 3-hydroxylase, a novel enzyme which hydroxylates free l-proline to cis-3-hydroxy-l-proline. J. Bacteriol. 179 (1997) 5677-5683
8. Shibasaki T., Mori H., Chiba S., and Ozaki A. Microbial proline 4-hydroxylase screening and gene cloning. Appl. Environ. Microbiol. 65 (1999) 4028-4031
9. Shibasaki T., Mori H., and Ozaki A. Enzymatic production of trans-4-hydroxy-l-proline by regio- and stereospecific hydroxylation of l-proline. Biosci. Biotechnol. Biochem. 64 (2000) 746-750
10. Shibasaki T., Hashimoto S., Mori H., and Ozaki A. Construction of a novel hydroxyproline-producing recombinant Escherichia coli by introducing a proline 4-hydroxylase gene. J. Biosci. Bioeng. 90 (2000) 522-525
11. Clifton I.J., Hsueh L.C., Baldwin J.E., Harlos K., and Schofield C.J. Structure of proline 3-hydroxylase, evolution of the family of 2-oxoglutarate dependent oxygenases. Eur. J. Biochem. 268 (2001) 6625-6636
12. Mori H., Shibasaki T., Uozaki Y., Ochiai K., and Ozaki A. Detection of novel proline 3-hydroxylase activities in Streptomyces and Bacillus spp. by regio- and stereospecific hydroxylation of l-proline. Appl. Environ. Microbiol. 62 (1996) 1903-1907
13. Bontoux M.C., and Gelo-Pujic M. Microbial screening in hydroxylation of l-proline. Tetrahedron Lett. 47 (2006) 9073-9076
14. Metzner L., Kalbitz J., and Brandsch M. Transport of pharmacologically active proline derivatives by the human proton-coupled amino acid transporter hPAT1. J. Pharmacol. Exp. Ther. 309 (2004) 28-35
15. Sambrook J., and Russell D.W. Molecular cloning: a laboratory manual. third ed. (2001), Cold Spring Harbor Laboratory Press, Cold Spring Harbor Laboratory, New York
16. Beringer J.E. R factor transfer in Rhizobium leguminosarum. J. Gen. Microbiol. 84 (1974) 188-198
17. Bradford M.M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72 (1976) 248-254
18. Fujii K., Ikai Y., Oka H., Suzuki M., and Harada K. A nonempirical method using LC/MS for determination of the absolute configuration of constituent amino acids in a peptide: Combination of Marfey's method with mass spectrometry and its practical application. Anal. Chem. 69 (1997) 5146-5151
19. Wieland T. Poisonous principles of mushrooms of the genus Amanita, four-carbon amines acting on the central nervous system and cell-destroying cyclic peptides are produced. Science 159 (1968) 946-952
20. Giri K.V., Gopalkrishnan K.S., Radhakrishnan A.N., and Vaidyanathan C.S. Proline and hydroxyproline in leaves. Nature 170 (1952) 579-580
21. Kuttan R., and Radhakrishnan A.N. The biosynthesis of cis-4-hydroxy-l-proline in sandal (Santalum album L.). Biochem. J. 117 (1970) 1015-1017
22. Kuttan R., and Radhakrishnan A.N. Studies on bound trans-4-hydroxy-l-proline in sandal (Santalum album L.). Biochem. J. 119 (1970) 651-657
23. Matsuoka T., Furuya K., and Serizawa N. Fermentative production of cis-4-hydroxy-(l)-proline by Helicocerus oryzae and Acrocylindrium oryzae. Biosci. Biotechnol. Biochem. 58 (1994) 1747-1748
24. Myllyla R., Gunzler V., Kivirikko K.I., and Kaska D.D. Modification of vertebrate and algal prolyl 4-hydroxylases and vertebrate lysyl hydroxylase by diethyl pyrocarbonate, Evidence for histidine residues in the catalytic site of 2-oxoglutarate-coupled dioxygenases. Biochem. J. 286 (1992) 923-927
25. Hausinger R.P. Fe(II)/alpha-ketoglutarate-dependent hydroxylases and related enzymes. Crit. Rev. Biochem. Mol. Biol. 39 (2004) 21-68
26. Clifton I.J., McDonough M.A., Ehrismann D., Kershaw N.J., Granatino N., and Schofield C.J. Structural studies on 2-oxoglutarate oxygenases and related double-stranded beta-helix fold proteins. J. Inorg. Biochem. 100 (2006) 644-669