Benzodiazepine Biosynthesis in Streptomyces refuineus (DOI:10.1016/j.chembiol.2007.05.009);Benzodiazepine Biosynthesis in Streptomyces refuineus

Chemistry and Biology

Volumn 14, Issue 6, 2007, Pages 691-701

  Hu, Yunfeng ^a   Phelan, Vanessa ^a   Ntai, Ioanna ^a   Farnet, Chris M ^b   Zazopoulos, Emmanuel ^b   Bachmann, Brian O ^a  

^a VANDERBILT UNIVERSITY   (United States)

^b INSTITUTE FOR RESEARCH IN IMMUNOLOGY AND CANCER   (Canada)

Author keywords

CHEMBIOL; MICROBIO

Indexed keywords

ACTINOBACTERIA; STREPTOMYCES; STREPTOMYCES REFUINEUS;

EID: 34250628482     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2007.07.006     Document Type: Erratum

References (40)

1. Decaudin D. Peripheral benzodiazepine receptor and its clinical targeting. Anticancer Drugs 15 (2004) 737-745
2. Zisterer D.M., and Williams D.C. Peripheral-type benzodiazepine receptors. Gen. Pharmacol. 29 (1997) 305-314
3. Tendler M.D., and Korman S. "Refuin": a non-cytotoxic carcinostatic compound proliferated by a thermophilic actinomycete. Nature 199 (1963) 501
4. Leimgruber W., Stefanov V., Schenker F., Karr A., and Berger J. Isolation and characterization of anthramycin a new antitumor antibiotic. J. Am. Chem. Soc. 87 (1965) 5791-5793
5. Leimgruber W., Batcho A.D., and Schenker F. Structure of anthramycin. J. Am. Chem. Soc. 87 (1965) 5793-5795
6. Kopka M.L., Goodsell D.S., Baikalov I., Grzeskowiak K., Cascio D., and Dickerson R.E. Crystal structure of a covalent DNA-drug adduct: anthramycin bound to C-C-A-A-C-G-T-T-G-G and a molecular explanation of specificity. Biochemistry 33 (1994) 13593-13610
7. Baraldi P.G., Bovero A., Fruttarolo F., Preti D., Tabrizi M.A., Pavani M.G., and Romagnoli R. DNA minor groove binders as potential antitumor and antimicrobial agents. Med. Res. Rev. 24 (2004) 475-528
8. Bachmann, B.O., McAlpine, J.B., Zazopoulos, E., Farnet, C.M., and Piraee, M. 2006. U.S. patent 7,101,872.
9. Charan R.D., Schlingmann G., Janso J., Bernan V., Feng X.D., and Carter G.T. Diazepinomicin, a new antimicrobial alkaloid from a marine Micromonospora sp. J. Nat. Prod. 67 (2004) 1431-1433
10. Farnet, C.M., Dimitriadou, V., and Bachmann, B.O. March 2007. U.S. patent 7,186,713.
11. Hurley L.H. Elucidation and formulation of novel biosynthetic pathways leading to the pyrrolo[1,4]benzodiazepine antibiotics anthramycin, tomaymycin, and sibiromycin. Acc. Chem. Res. 13 (1980) 263-269
12. Hurley L., Das N., Gairola C., and Zmijewski M. Biosynthetic incorporation of Dl-tryptophan-(5-H-3) into anthramycin, sibiromycin and tomaymycin-Nih shift produced by actinomycetes. Tetrahedron Lett. 18 (1976) 1419-1422
13. Hurley L.H., Zmijewski M., and Chang C.J. Biosynthesis of anthramycin-determination of labeling pattern by use of radioactive and stable isotope techniques. J. Am. Chem. Soc. 97 (1975) 4372-4378
14. Brahme N.M., Gonzalez J.E., Rolls J.P., Hessler E.J., Mizsak S., and Hurley L.H. Biosynthesis of the lincomycins. 1. Studies using stable isotopes on the biosynthesis of the propyl-L-hygric and ethyl-L-hygric acid moieties of lincomycin-a and lincomycin-B. J. Am. Chem. Soc. 106 (1984) 7873-7878
15. Zazopoulos E., Huang K., Staffa A., Liu W., Bachmann B.O., Nonaka K., Ahlert J., Thorson J.S., Shen B., and Farnet C.M. A genomics-guided approach for discovering and expressing cryptic metabolic pathways. Nat. Biotechnol. 21 (2003) 187-190
16. Gust B., Challis G.L., Fowler K., Kieser T., and Chater K.F. PCR-targeted Streptomyces gene replacement identifies a protein domain needed for biosynthesis of the sesquiterpene soil odor geosmin. Proc. Natl. Acad. Sci. USA 100 (2003) 1541-1546
17. Sosio M., Giusino F., Cappellano C., Bossi E., Puglia A.M., and Donadio S. Artificial chromosomes for antibiotic-producing actinomycetes. Nat. Biotechnol. 18 (2000) 343-345
18. Keller U., Kleinkauf H., and Zocher R. 4-Methyl-3-hydroxyanthranilic acid activating enzyme from actinomycin-producing Streptomyces chrysomallus. Biochemistry 23 (1984) 1479-1484
19. Dalgliesh C.E., and Todd A.R. Actinomycin. Nature 164 (1949) 820
20. Velasco A., Acebo P., Gomez A., Schleissner C., Rodriguez P., Aparicio T., Conde S., Muñoz R., de la Calle F., Garcia J.L., and Sánchez-Puelles J.M. Molecular characterization of the safracin biosynthetic pathway from Pseudomonas fluorescens A2-2: designing new cytotoxic compounds. Mol. Microbiol. 56 (2005) 144-154
21. Peschke U., Schmidt H., Zhang H.Z., and Piepersberg W. Molecular characterization of the lincomycin-production gene-cluster of Streptomyces lincolnensis-78-11. Mol. Microbiol. 16 (1995) 1137-1156
22. Novotna J., Honzatko A., Bednar P., Kopecky J., Janata J., and Spizek J. L-3,4-dihydroxyphenyl alanine-extradiol cleavage is followed by intramolecular cyclization in lincomycin biosynthesis. Eur. J. Biochem. 271 (2004) 3678-3683
23. Neusser D., Schmidt H., Spizek J., Novotna J., Peschke U., Kaschabeck S., Tichy P., and Piepersberg W. The genes lmbB1 and lmbB2 of Streptomyces lincolnensis encode enzymes involved in the conversion of L-tyrosine to propylproline during the biosynthesis of the antibiotic lincomycin A. Arch. Microbiol. 169 (1998) 322-332
24. Challis G.L., and Naismith J.H. Structural aspects of non-ribosomal peptide biosynthesis. Curr. Opin. Struct. Biol. 14 (2004) 748-756
25. Finking R., and Marahiel M.A. Biosynthesis of nonribosomal peptides1. Annu. Rev. Microbiol. 58 (2004) 453-488
26. Schwarzer D., Finking R., and Marahiel M.A. Nonribosomal peptides: from genes to products. Nat. Prod. Rep. 20 (2003) 275-287
27. Pospiech A., Bietenhader J., and Schupp T. Two multifunctional peptide synthetases and an O-methyltransferase are involved in the biosynthesis of the DNA-binding antibiotic and antitumour agent saframycin Mx1 from Myxococcus xanthus. Microbiol. 142 (1996) 741-746
28. Gaitatzis N., Kunze B., and Muller R. In vitro reconstitution of the myxochelin biosynthetic machinery of Stigmatella aurantiaca Sg a15: biochemical characterization of a reductive release mechanism from nonribosomal peptide synthetases. Proc. Natl. Acad. Sci. USA 98 (2001) 11136-11141
29. Kopp F., Mahlert C., Grunewald J., and Marahiel M.A. Peptide macrocyclization: the reductase of the nostocyclopeptide synthetase triggers the self-assembly of a macrocyclic imine. J. Am. Chem. Soc. 128 (2006) 16478-16479
30. Sims J.W., Fillmore J.P., Warner D.D., and Schmidt E.W. Equisetin biosynthesis in Fusarium heterosporum. Chem. Commun. (Camb.) 2 (2005) 186-188
31. Challis G.L., Ravel J., and Townsend C.A. Predictive, structure-based model of amino acid recognition by nonribosomal peptide synthetase adenylation domains. Chem. Biol. 7 (2000) 211-224
32. Stachelhaus T., Mootz H.D., and Marahiel M.A. The specificity-conferring code of adenylation domains in nonribosomal peptide synthetases. Chem. Biol. 6 (1999) 493-505
33. Jones G.H. Combined purification of actinomycin synthetase-I and 3-hydroxyanthranilic acid 4-methyltransferase from Streptomyces antibioticus. J. Biol. Chem. 268 (1993) 6831-6834
34. Liu W., Christenson S.D., Standage S., and Shen B. Biosynthesis of the enediyne antitumor antibiotic C-1027. Science 297 (2002) 1170-1173
35. Lomovskaya N., Hong S.K., Kim S.U., Fonstein L., Furuya K., and Hutchinson R.C. The Streptomyces peucetius drrC gene encodes a UvrA-like protein involved in daunorubicin resistance and production. J. Bacteriol. 178 (1996) 3238-3245
36. Wang L., and Vining L.C. Control of growth, secondary metabolism and sporulation in Streptomyces venezuelae ISP5230 by jadW(1), a member of the afsA family of gamma-butyrolactone regulatory genes. Microbiol. 149 (2003) 1991-2004
37. Kieser T., Hopwood D.A., Wright H.M., and Thompson C.J. pIJ101, a multi-copy broad host-range Streptomyces plasmid: functional analysis and development of DNA cloning vectors. Mol. Gen. Genet. 185 (1982) 223-228
38. Altschul S.F. A protein alignment scoring system sensitive at all evolutionary distances. J. Mol. Evol. 36 (1993) 290-300
39. Altschul S.F., and Lipman D.J. Protein database searches for multiple alignments. Proc. Natl. Acad. Sci. USA 87 (1990) 5509-5513
40. Fleischmann R.D., Adams M.D., White O., Clayton R.A., Kirkness E.F., Kerlavage A.R., Bult C.J., Tomb J.F., Dougherty B.A., Merrick J.M., et al. Whole-genome random sequencing and assembly of Haemophilus influenzae Rd. Science 269 (1995) 496-512