Enzymatic production of trans-4-hydroxy-L-proline by regio- and stereospecific hydroxylation of l-proline

Bioscience, Biotechnology and Biochemistry

Volumn 64, Issue 4, 2000, Pages 746-750

  Shibasaki, Takeshi ^a   Mori, Hideo ^a   Ozaki, Akio ^a  

^a KYOWA HAKKO KOGYO CO LTD   (Japan)

Author keywords

2 oxoglutarate dependent dioxygenase; Bioconversion; Hydroxyproline; Proline; Proline 4 hydroxylase

Indexed keywords

DACTYLOSPORANGIUM SP.; ESCHERICHIA COLI;

2 OXOGLUTARIC ACID; ALPHA-KETOGLUTARIC ACID; CARBOXYLIC ACID; DRUG DERIVATIVE; HYDROXYPROLINE; PROCOLLAGEN PROLINE 2 OXOGLUTARATE 4 DIOXYGENASE; PROLINE;

AMINO ACID SEQUENCE; ARTICLE; BIOSYNTHESIS; GENE EXPRESSION; GENE VECTOR; GENETICS; HYDROXYLATION; METABOLISM; MOLECULAR GENETICS; NUCLEOTIDE SEQUENCE; PLASMID; STEREOISOMERISM;

AMINO ACID SEQUENCE; BASE SEQUENCE; CARBOXYLIC ACIDS; GENE EXPRESSION; GENETIC VECTORS; HYDROXYLATION; HYDROXYPROLINE; KETOGLUTARIC ACIDS; MOLECULAR SEQUENCE DATA; PLASMIDS; PROCOLLAGEN-PROLINE DIOXYGENASE; PROLINE; STEREOISOMERISM;

EID: 0034170020     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.64.746     Document Type: Article

References (27)

1. Remuzon, P., traαs-4-Hydroxy-L-proline, a useful and versatile chiral starting block. Tetrahedron, 52, 13803-13835 (1996).
2. Seki, M. and Matsumoto, K., A convenient synthesis of (25,45)-4-hydroxyproline. Biosci. Biotechnol. Biochem., 59, 1161-1162 (1995).
3. Baker, G. L., Fritschel, S. J., Stille, J. R., and Stille, J. K., Transition-metal-catalyzed asymmetric organic synthesis via polymer-attached optically active phosphine ligands. 5.1 Preparation of amino acids in high optically yield via catalytic hydrogenation. J. Org. Chem., 46, 2954-2960 (1981).
4. Katsumata, R. and Yokoi, H., Japan Kokai Tokkyo Koho, H03-266995 (Nov. 27, 1991).
5. Katsumata, R., Hashimoto, S., Ikeda, M., Kawanishi, M., and Sakado, K., Japan Kokai Tokkyo Koho, H06-062880 (Mar. 8, 1994).
6. Serizawa, N., Matsuoka, T., Hosoya, T., and Furuya, K., Fermentative production of trans-4-hydroxy-L-proline by Clonostachys cylindrospora. Biosci. Biotechnol. Biochem., 59, 555-557 (1995).
7. Matsuoka, T., Serizawa, N., Hosoya, T., and Furuya, K., Japan Kokai Tokkyo Koho, H05-236980 (Sep. 18, 1993).
8. Maruhashi, K., Japan Kokai Tokkyo Koho, H09-173093 (Jul. 8, 1997).
9. Iizuka, S., Matsuura, Y., Nemoto, A., Ishihara, M., Takase, I., and Miyashiro, S., Japan Kokai Tokkyo Koho, H06-245782 (Sep. 6, 1994).
10. Cardinale, G. J. and Udenfriend, S., Prolyl hydroxylase. Adv. Enzymol., 41, 245-300 (1974).
11. Katz, E., Kamal, F., and Mason, K., Biosynthesis of trans-4-hydroxy-L-proline by Streptomyces griseoviri-dus. J. Biol. Chem., 254, 6684-6690 (1979).
12. Onishi, M., Okumura, Y., Okamoto, R., and Ishikura, T., Proline hydroxylation by cell free extract of a streptomycete. Biochem. Biophys. Res. Commun., 120, 45-51 (1984).
13. 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, 185-191 (1996).
14. Shibasaki, T., Mori, H., Chiba S., and Ozaki A., Microbial proline 4-hydroxylase screening and gene cloning. Appl. Environ. Microbiol., 65, 4028-4031 (1999).
15. Ozaki, A., Shibasaki, T., and Mori, H., Specific proline and hydroxyproline detection method by postcolumn derivatization for high-performance liquid chromatography. Biosci. Biotechnol. Biochem., 59, 1764-1765 (1995).
16. Nishi, T., Saito, A., Oka, T., Itoh, S., Takaoka, C., and Taniguchi, T., Construction of plasmid expression vectors carrying the Escherichia coli tryptophan promoter. Agric. Biol. Chem., 48, 669-675 (1984).
17. Caro, L. and Berg, C. M., PI transduction. Methods Enzymol., 21, 444-458 (1971).
18. Dassa, E. and Boquet, P. L., Identification of the gene appA for the acid phosphatase (pH optimum 2.5) of Escherichia coli. Mol. Gen. Genet., 200, 68-73 (1985).
19. Bochner, B. R. and Savageau, M. A., Generalized indicator plate for genetic, metabolic, and taxonomic studies with microorganisms. Applied. Environ. Microbiol., 33, 434-444 (1977).
20. de Boer, H. A., Comstock, L. J., and Yasser, M., The tac promoter: A functional hybrid derived from the trp and lac promoters. Proc. Natl. Acad. Sci. USA, 80, 21-25 (1983).
21. Andersson, S. G. E. and Kurland, C. G., Codon preferences in free-living microorganisms. Microbiol. Rev., 54, 198-210 (1990).
22. Wada, K., Wada, Y., Ishibashi, F., Gojobori, T., and Ikemura, T., Codon usage tabulated from Gen-Bank genetic sequence data. Nucleic Acids Res., 20, 2111-2118 (1992).
23. Goldman, E., Rosenburg, A. H., Zubay, G., and Studier, F. W., Consecutive low-usage leucine codons block translation only when near the 5' end of a message in Escherichia coli. J. Mol. Biol., 245, 467-473 (1995).
24. Yokota, A., Shimizu, H., Terasawa, Y., Takaoka, N., and Tomita, F., Pyruvic acid production by a lipoic acid auxotroph of Escherichia coli W1485. Appl. Microbiol. Biotechnol., 41, 638-643 (1994).
25. ndedition”, eds. Neidhardt, F. C., et ah, ASM Press, Washington DC, pp. 358-379 (1996).
26. 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 cA-3-hydroxy-L-proline. J. Bacteriol., 179, 5677-5683 (1997).
27. Shibasaki, T., Sakurai, W., Hasegawa, A., Uosaki, Y., Mori, H., Yoshida, M., and Ozaki, A., Substrate selectivities of proline hydroxylases. Tetrahedron Lett., 40, 5227-5230 (1999).