Cytochrome P450 homolog is responsible for C-N bond formation between aglycone and deoxysugar in the staurosporine biosynthesis of Streptomyces sp. TP-A0274

Bioscience, Biotechnology and Biochemistry

Volumn 69, Issue 9, 2005, Pages 1753-1759

  Onaka, Hiroyasu ^a   Asamizu, Shumpei ^a   Igarashi, Yasuhiro ^a   Yoshida, Ryuji ^a   Furumai, Tamotsu ^a  

^a TOYAMA PREFECTURAL UNIVERSITY   (Japan)

Author keywords

Biosynthesis; Cytochrome P450; Indolocarbazole; Staurosporine; Streptomyces

Indexed keywords

BIOSYNTHESIS; CATALYSIS; CATALYSTS; CHEMICAL BONDS; NITROGEN; SUGARS;

CYTOCHROME P450; INDOLOCARBAZOLES; STAUROSPORINES; STREPTOMYCES;

GENES;

7 DEOXY 13 DIHYDROADRIAMYCINONE; 7-DEOXY-13-DIHYDROADRIAMYCINONE; AMINE; CARBAZOLE DERIVATIVE; CYTOCHROME P450; DEOXYSUGAR; DOXORUBICIN; DRUG DERIVATIVE; INDOLE DERIVATIVE; REBECCAMYCIN; STAUROSPORINE;

AMINO ACID SEQUENCE; ARTICLE; BIOSYNTHESIS; CHEMICAL MODEL; CHEMISTRY; ENZYMOLOGY; GENETICS; METABOLISM; MOLECULAR GENETICS; MUTATION; SEQUENCE HOMOLOGY; STREPTOMYCES; THEORETICAL MODEL;

AMINES; AMINO ACID SEQUENCE; CARBAZOLES; CYTOCHROME P-450 ENZYME SYSTEM; DEOXY SUGARS; DOXORUBICIN; INDOLES; MODELS, CHEMICAL; MODELS, THEORETICAL; MOLECULAR SEQUENCE DATA; MUTATION; SEQUENCE HOMOLOGY, AMINO ACID; STAUROSPORINE; STREPTOMYCES;

STREPTOMYCES; STREPTOMYCES SP.;

EID: 25844485154     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.69.1753     Document Type: Article

References (17)

1. Omura, S., Sasaki, Y., Iwai, Y., and Takesima, H., Staurosporine, a potentially important gift from a microorganism. J. Antibiotics, 48, 535-548 (1995).
2. Onaka, H., Taniguchi, S., Igarashi, Y., and Furumai, T., Cloning of the staurosporine biosynthetic gene cluster from Streptomyces sp. TP-A0274 and its heterologous expression in Streptomyces lividans. J. Antibiotics, 55, 1063-1071 (2002).
3. Sanchez, C., Zhu, L., Brana, A. F., Salas, A. P., Rohr, J., Mendez, C., and Salas, J. A., Combinatorial biosynthesis of antitumor indolocarbazole compounds. Proc. Natl. Acad. Sci. U.S.A., 102, 461-466 (2005).
4. Sanchez, C., Butovich, I. A., Brana, A. F., Rohr, J., Mendez, C., and Salas, J. A., The biosynthetic gene cluster for the antitumor rebeccamycin: characterization and generation of indolocarbazole derivatives. Chem. Biol., 9, 519-531 (2002).
5. Onaka, H., Taniguchi, S., Igarashi, Y., and Furumai, T., Characterization of the biosynthetic gene cluster of rebeccamycin from Lechevalieria aerocolonigenes ATCC 39243. Biosci. Biotechnol. Biochem., 67, 127-138 (2003).
6. Andersen, J. F., and Hutchinson, C. R., Characterization of Saccharopolyspora erythraea cytochrome P-450 genes and enzymes, including 6-deoxyerythronolide B hydroxylase. J. Bacteriol., 174, 725-735 (1992).
7. Mazodier, P., Petter, R., and Thompson, C., Intergeneric conjugation between Escherichia coli and Streptomyces species. J. Bacteriol., 171, 3583-3585 (1989).
8. Schafer, A., Tauch, A., Jager, W., Kalinowski, J., Thierbach, G., and Puhler, A., Small mobilizable multi-purpose cloning vectors derived from the Escherichia coli plasmids pK18 and pK19: selection of defined deletions in the chromosome of Corynebacterium glutamicum. Gene, 145, 69-73 (1994).
9. Sambrook, J., and Russell, D. W., Molecular cloning: a laboratory manual, third ed., Cold Spring Harbor Laboratory Press, NY (2001).
10. Onaka, H., Tabata, H., Igarashi, Y., Sato, Y., and Furumai, T., Goadsporin, a chemical substance which promotes secondary metabolism and morphogenesis in streptomycetes. I. Purification and characterization. J. Antibiotics, 54, 1036-1044 (2001).
11. Kieser, T., Bibb, M. J., Buttner, M. J., Chater, K. F., and Hopwood, D. A., "Practical Streptomyces Genetics", John Innes Foundation, Norwich (2000).
12. Pang, C. H., Shiiyama, M., Ikeda, H., Tanaka, H., and Omura S., Cosmid vector for cloning and analysis of Streptomyces DNA. Actinomycetol., 8, 21-25 (1994).
13. Williams, D. E., Bernan, V. S., Ritacco, F. V., Maiese, W. M., Greenstein, M., and Andersen, R. J., Holyrines A and B, possible intermediates in staurosporine biosynthesis produced in culture by a marine actinomycete obtained from the North Atlantic Ocean. Tetrahedron Lett., 40, 7171-7174 (1999).
14. Kase, H., Iwahashi, K., and Matsuda, Y., K-252a, a potent inhibitor of protein kinase C of microbial origin. J. Antibiotics, 39, 1059-1065 (1986).
15. Akinaga, S., Sugiyama, K., and Akiyama, T., UCN-01 (7- hydroxystaurosporine) and other indolocarbazole compounds: a new generation of anti-cancer agents for the new century? Anticancer Drug Des., 15, 43-52 (2000).
16. Takahashi, H., Osada, H., Uramoto, M., and Isono, K., A new inhibitor of protein kinase C, RK-286C (4′-demethylamino-4′-hydroxystaurosporine) . II. Isolation, physico-chemical properties and structure. J. Antibiotics, 43, 168-173 (1990).
17. Hoehn, P., Ghisalba, O., Moerker, T., and Peters, H. H., 3′-Demethoxy-3′-hydroxystaurosporine, a novel staurosporine analogue produced by a blocked mutant. J. Antibiotics, 48, 300-305 (1995).