Conversion of vitamin D3 to 1α,25-dihydroxyvitamin D 3 by Streptomyces griseolus cytochrome P450SU-1

Biochemical and Biophysical Research Communications

Volumn 320, Issue 1, 2004, Pages 156-164

  Sawada, Natsumi ^a   Sakaki, Toshiyuki ^a,b   Yoneda, Sachiyo ^a   Kusudo, Tatsuya ^a   Shinkyo, Raku ^a   Ohta, Miho ^c   Inouye, Kuniyo ^a  

^a KYOTO UNIVERSITY   (Japan)

^b TOYAMA PREFECTURAL UNIVERSITY   (Japan)

^c Koshien Junior College   (Japan)

Author keywords

1 Hydroxylation of 25 hydroxyvitamin D3; CYP105A1; CYP27A1; Hydroxylation of vitamin D3; Streptomyces P450

Indexed keywords

1,25 DIHYDROXYERGOCALCIFEROL; 24 HYDROXYERGOCALCIFEROL; 27 HYDROXYERGOCALCIFEROL; BACTERIAL ENZYME; CALCITRIOL; COLECALCIFEROL; CYTOCHROME P450; CYTOCHROME P450 27A1; CYTOCHROME P450 SU 1; ERGOCALCIFEROL; ERGOCALCIFEROL DERIVATIVE; MITOCHONDRIAL ENZYME; UNCLASSIFIED DRUG; BACTERIAL PROTEIN; OXYGENASE; P450SU1 PROTEIN, STREPTOMYCES GRISEOLUS; RECOMBINANT PROTEIN;

ARTICLE; BACTERIUM CULTURE; CATALYSIS; ENZYME ACTIVITY; ESCHERICHIA COLI; HYDROXYLATION; METABOLITE; NONHUMAN; PRIORITY JOURNAL; PROTEIN PURIFICATION; STREPTOMYCES; STREPTOMYCES GRISEOLUS; BACTERIUM TRANSFORMATION; BIOSYNTHESIS; CHEMISTRY; COMPARATIVE STUDY; ENZYME ACTIVATION; ENZYMOLOGY; EVALUATION; GENETICS; HUMAN; ISOLATION AND PURIFICATION; METHODOLOGY; MOLECULAR WEIGHT; PROTEIN ENGINEERING; SYNTHESIS;

ESCHERICHIA COLI; MAMMALIA; STREPTOMYCES; STREPTOMYCES GRISEOLUS;

BACTERIAL PROTEINS; CALCITRIOL; CHOLECALCIFEROL; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME ACTIVATION; ESCHERICHIA COLI; HUMANS; MOLECULAR WEIGHT; OXYGENASES; PROTEIN ENGINEERING; RECOMBINANT PROTEINS; STREPTOMYCES; TRANSFORMATION, BACTERIAL;

EID: 2942691384     PISSN: 0006291X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbrc.2004.05.140     Document Type: Article

References (40)

1. Lamb D.C., Skaug T., Song H.L., Jackson C.J., Podust L.M., Waterman M.R., Kelly D.E., Kelly S.L. The cytochrome P450 complement (CYPome) of Streptomyces coelicolor A3(2). J. Biol. Chem. 277:2002;24000-24005
2. Healy F.G., Krasnoff S.B., Wach M., Gibson D.M., Loria R. Involvement of a cytochrome P450 monooxygenase in thaxtomin A biosynthesis by Streptomyces acidiscabies. J. Bacteriol. 184:2002;2019-2029
3. Bruntner C., Lauer B., Schwarz W., Mohrle V., Bormann C. Molecular characterization of co-transcribed genes from Streptomyces tendae Tu901 involved in the biosynthesis of the peptidyl moiety of the peptidyl nucleoside antibiotic nikkomycin. Mol. Gen. Genet. 262:1999;102-114
4. Fouces R., Mellado E., Diez B., Barredo J.L. The tylosin biosynthetic cluster from Streptomyces fradiae: genetic organization of the left region. Microbiology. 145(Pt. 4):1999;855-868
5. Lomovskaya N., Otten S.L., Doi-Katayama Y., Fonstein L., Liu X.C., Takatsu T., Inventi-Solari A., Filippini S., Torti F., Colombo A.L., Hutchinson C.R. Doxorubicin overproduction in Streptomyces peucetius: cloning and characterization of the dnrU ketoreductase and dnrV genes and the doxA cytochrome P-450 hydroxylase gene. J. Bacteriol. 181:1999;305-318
6. Tang L., Shah S., Chung L., Carney J., Katz L., Khosla C., Julien B. Cloning and heterologous expression of the epothilone gene cluster. Science. 287:2000;640-642
7. Walczak R.J., Hines J.V., Strohl W.R., Priestley N.D. Bioconversion of the anthracycline analogue desacetyladriamycin by recombinant DoxA, a P450-monooxygenase from Streptomyces sp. strain C5. Org. Lett. 3:2001;2277-2279
8. Matsuoka T., Miyakoshi S., Tanzawa K., Nakahara K., Hosobuchi M., Serizawa N. Purification and characterization of cytochrome P-450sca from Streptomyces carbophilus. ML-236B (compactin) induces a cytochrome P-450sca in Streptomyces carbophilus that hydroxylates ML-236B to pravastatin sodium (CS-514), a tissue-selective inhibitor of 3-hydroxy-3-methylglutaryl-coenzyme-A reductase. Eur. J. Biochem. 184:1989;707-713
9. Serizawa N., Matsuoka T. A two component-type cytochrome P-450 monooxygenase system in a prokaryote that catalyzes hydroxylation of ML-236B to pravastatin, a tissue-selective inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A reductase. Biochim. Biophys. Acta. 1084:1991;35-40
10. 3 by using Streptomyces sp. strains. Appl. Environ. Microbiol. 57:1991;2841-2846
11. 3 using Amycolata sp. strains. Appl. Microbiol. Biotechnol. 38:1992;152-157
12. 3 25-hydroxylase. Biochim. Biophys. Acta. 1219:1994;179-183
13. Omer C.A., Lenstra R., Litle P.J., Dean C., Tepperman J.M., Leto K.J., Romesser J.A., O'Keefe D.P. Genes for two herbicide-inducible cytochromes P-450 from Streptomyces griseolus. J. Bacteriol. 172:1990;3335-3345
14. O'Keefe D.P., Bozak K.R., Christoffersen R.E., Tepperman J.A., Dean C., Harder P.A. Endogenous and engineered cytochrome P-450 mono-oxygenases in plants. Biochem. Soc. Trans. 20:1992;357-361
15. Taylor M., Lamb D.C., Cannell R., Dawson M., Kelly S.L. Cytochrome P450105D1 (CYP105D1) from Streptomyces griseus: heterologous expression, activity, and activation effects of multiple xenobiotics. Biochem. Biophys. Res. Commun. 263:1999;838-842
16. 3 by CYP27A1. Biochem. Biophys. Res. Commun. 273:2000;977-984
17. Akiyoshi-Shibata M., Sakaki T., Ohyama Y., Noshiro M., Okuda K., Yabusaki Y. Further oxidation of hydroxycalcidiol by calcidiol 24-hydroxylase. Eur. J. Biochem. 224:1994;335-343
18. Kondo S., Sakaki T., Ohkawa H., Inouye K. Electrostatic interaction between cytochrome P450 and NADPH-P450 reductase: comparison of mixed and fused systems consisting of rat cytochrome P4501A1 and yeast NADPH-P450 reductase. Biochem. Biophys. Res. Commun. 257:1999;273-278
19. Omura T., Sato R. The carbon monoxide-binding pigment of liver microsomes. II. Solubilisation, purification, and properties. J. Biol. Chem. 239:1964;2379-2385
20. Waxman D.J., Walsh C. Phenobarbital-induced rat liver cytochrome P-450. Purification and characterization of two closely related isozymic forms. J. Biol. Chem. 257:1982;10446-10457
21. O'Keefe D.P., Gibson K.J., Emptage M.H., Lenstra R., Romesser J.A., Litle P.J., Omer C.A. Ferredoxins from two sulfonylurea herbicide monooxygenase systems in Streptomyces griseolus. Biochemistry. 30:1991;447-455
22. 3 analogs and their 3-epimers on human promyelocytic leukemia (HL-60) cell differentiation and apoptosis. Steroids. 66:2001;327-337
23. 3-1α-hydroxylase) of bovine kidney mitochondria. Biochem. Biophys. Res. Commun. 105:1982;320-327
24. Lowry O.H., Rosebrough N.J., Farr A.L., Randall R.J. Protein measurement with the folin phenol reagent. J. Biol. Chem. 193:1951;265-275
25. Hussain H.A., Ward J.M. Enhanced heterologous expression of two Streptomyces griseolus cytochrome P450s and Streptomyces coelicolor ferredoxin reductase as potentially efficient hydroxylation catalysts. Appl. Environ. Microbiol. 69:2003;373-382
26. Guo Y.D., Strugnell S., Back D.W., Jones G. Transfected human liver cytochrome P-450 hydroxylates vitamin D analogs at different side-chain positions. Proc. Natl. Acad. Sci. USA. 90:1993;8668-8672
27. 3 1alpha-hydroxylase gene in patients with pseudovitamin D-deficiency rickets. N. Engl. J. Med. 338:1998;653-661
28. 3-1α- hydroxylase and mutations causing vitamin D dependent rickets type I. Mol. Endocrinol. 11:1997;1961-1970
29. Poulos T.L., Finzel B.C., Gunsalus I.C., Wagner G.C., Kraut J. The 2.6-Å crystal structure of Pseudomonas putida cytochrome P-450. J. Biol. Chem. 260:1985;16122-16130
30. Ravichandran K.G., Boddupalli S.S., Hasermann C.A., Peterson J.A., Deisenhofer J. Crystal structure of hemoprotein domain of P450BM-3, a prototype for microsomal P450's. Science. 261:1993;731-736
31. Hasemann C.A., Ravichandran K.G., Peterson J.A., Deisenhofer J. Crystal structure and refinement of cytochrome P450terp at 2.3. Å resolution J. Mol. Biol. 236:1994;1169-1185
32. Cupp-Vickery J.R., Poulos T.L. Structure of cytochrome P450eryF involved in erythromycin biosynthesis. Nat. Struct. Biol. 2:1995;144-153
33. Park S.Y., Shimizu H., Adachi S., Nakagava A., Tanaka I., Nakahara K., Shoun H., Obayashi E., Nakamura H., Iizuka T., Shiro Y. Crystal structure of nitric oxide reductase from denitrifying fungus Fusarium oxysporum. Nat. Struct. Biol. 4:1997;827-832
34. Yano J.K., Koo L.S., Schuller L.D.J., Li H., Montellano P.R.O., Poulos T.L. Crystal structure of a thermophilic cytochrome P450 from the Archaeon Sulfolobus solfataricus. J. Biol. Chem. 275:2000;31086-31092
35. Podust L.M., Poulos T.L., Waterman M.R. Crystal structure of cytochrome P450 14alpha-sterol demethylase (CYP51) from Mycobacterium tuberculosis in complex with azole inhibitors. Proc. Natl. Acad. Sci. USA. 98:2001;3068-3073
36. Podust L.M., Kim Y., Arase M., Neely B.A., Beck B.J., Bach H., Sherman D.H., Lamb D.C., Kelly S.L., Waterman M.R. The 1.92-Å structure of Streptomyces coelicolor A3(2) CYP154C1. A new monooxygenase that functionalizes macrolide ring systems. J. Biol. Chem. 278:2003;12214-12221
37. Williams P.A., Comse J., Sridhar V., Johnson E.F., McRee D.E. Mammalian microsomal cytochrome P450 monooxygenase: structural adaptations for membrane binding and functional diversity. Mol. Cell. 5:2000;121-131
38. 3 1α-hydroxylase expressed in Escherichia coli. Eur. J. Biochem. 259:1999;731-738
39. 3 1α-hydroxylase. Eur. J. Biochem. 265:1999;950-956
40. Sawada N., Sakaki T., Kitanaka S., Kato S., Inouye K. Structure-function analysis of CYP27B1 and CYP27A1. Studies on mutants from patients with vitamin D-dependent rickets type I (VDDR-I) and cerebrotendinous xanthomatosis (CTX). Eur. J. Biochem. 268:2001;6607-6615