The leptomycin gene cluster and its heterologous expression in Streptomyces lividans

Journal of Antibiotics

Volumn 58, Issue 10, 2005, Pages 625-633

  Hu, Zhihao ^a   Reid, Ralph ^a   Gramajo, Hugo ^a  

^a KOSAN BIOSCIENCES INC   (United States)

Author keywords

Heterologous expression; Leptomycin; Nuclear export inhibitor

Indexed keywords

ANGUINOMYCIN A; ANTIBIOTIC AGENT; ANTIFUNGAL AGENT; ANTINEOPLASTIC AGENT; CALLYSTATIN A; CYTOCHROME P450; DNA; KAZUSAMYCIN A; KAZUSAMYCIN B; LEPTOFURANIN A; LEPTOLSTATIN; LEPTOMYCIN A; LEPTOMYCIN B; MALONYL COENZYME A; NATURAL PRODUCT; POLYKETIDE SYNTHASE; RATJADONE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; DRUG SYNTHESIS; EUKARYOTIC CELL; GENE; GENE CLUSTER; GENE EXPRESSION; GENE SEQUENCE; GENETIC ENGINEERING; LEPA GENE; LEPB GENE; LEPC GENE; LEPD GENE; LEPTOMYCIN GENE; MOLECULAR CLONING; NONHUMAN; NUCLEOCYTOPLASMIC TRANSPORT; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; STREPTOMYCES LIVIDANS;

EUKARYOTA; STREPTOMYCES LIVIDANS; STREPTOMYCES SP.;

EID: 28244498432     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.1038/ja.2005.86     Document Type: Article

References (52)

1. Hamamoto T, Gunji S, Tsuji H, Beppu T. Leptomycins A and B, new antifungal antibiotics. I. Taxonomy of the producing strain and their fermentation, purification and characterization. J Antibiot 36: 639-645 (1983)
2. Hamamoto T, Seto H, Beppu T. Leptomycins A and B, new antifungal antibiotics. II. Structure elucidation. J Antibiot 36: 646-650 (1983).
3. Gerth K, Schumme D, Hofle G, Irschik H, Reichenbach H. Ratjadon: a new antifungal compound from Sorangium cellulosum (myxobacteria) production, physico-chemical and biological properties. J Antibiot 48: 973-976 (1995)
4. Komiyama K, Okada K, Oka H, Tomisaka S, Miyano T, Funayama S, Umezawa I. Structural study of a new antitumor antibiotic, kazusamycin. J Antibiot 38: 220-229 (1985)
5. Komiyama K, Okada K, Hirokawa Y, Masuda K, Tomisaka S, Umezawa I. Antitumor activity of a new antibiotic, kazusamycin. J Antibiot 38: 224-229 (1985)
6. Umezawa I, Komiyama K, Oka H, Okada K, Tomisaka S, Miyano T, Takano S. A new antitumor antibiotic, kazusamycin. J Antibiot 37: 706-711 (1984)
7. Hayakawa Y, Sohda KY, Shin-Ya K, Hidaka T, Seto H. Anguinomycins C and D, new antitumor antibiotics with selective cytotoxicity against transformed cells. J Antibiot 48: 954-961 (1995)
8. Hayakawa Y, Adachi K, Komeshima N. New antitumor antibiotics, anguinomycins A and B. J Antibiot 40:1349-1352 (1987)
9. Hayakawa Y, Sohda K, Seto H. Studies on new antitumor antibiotics, leptofuranins A, B, C and D. II. Physicochemical properties and structure elucidation. J Antibiot 49: 980-984 (1996)
10. Hayakawa Y, Sohda K, Furihata K, Kuzuyama T, Shin-ya K, Seto H. Studies on new antitumor antibiotics, leptofuranins A, B, C and D. I. Taxonomy, fermentation, isolation and biological activities. J Antibiot 49: 974-979 (1996)
11. Abe K, Yoshida M, Horinouchi S, Beppu T. Leptolstatin from Streptomyces sp. SAM1595, a new gap phase-specific inhibitor of the mammalian cell cycle. I. Screening, taxonomy, purification and biological activities. J Antibiot 46: 728-734 (1993)
12. Abe K, Yoshida M, Naoki H, Horinouchi S, Beppu T. Leptolstatin from Streptomyces sp. SAM1595, a new gap phase-specific inhibitor of the mammalian cell cycle. II. Physico-chemical properties and structure. J Antibiot 46: 735-740 (1993)
13. Kobayashi M, Kitagawa I. Marine spongean cytotoxins. J Nat Toxins 8: 249-258 (1999)
14. Scheifele LZ, Ryan EP, Parent LJ. Detailed mapping of the nuclear export signal in the Rous sarcoma virus Gag protein. J Virol 79: 8732-8741 (2005)
15. Dangel AW, Hull S, Roberts TM, Boris-Lawrie K. Nuclear interactions are necessary for translational enhancement by spleen necrosis virus RU5. J Virol 76: 3292-3300 (2002)
16. DeLong LJ, Bonamy GM, Fink EN, Allison LA. Nuclear export of the oncoprotein v-ErbA is mediated by acquisition of a viral nuclear export sequence. J Biol Chem 279: 15356-15367 (2004)
17. Yoshida M, Horinouchi S. Trichostatin and leptomycin: Inhibition of Histone deacetylation and signal-dependent nuclear export. Ann NY Acad Sci 886: 23-35 (1999)
18. Strunze S, Trotman LC, Boucke K, Greber UF. Nuclear targeting of adenovirus type 2 requires CRM1-mediated nuclear export. Mol Biol Cell 16: 2999-3009 (2005)
19. Kudo N, Matsumori N, Taoka H, Fujiwara D, Schreiner EP, Wolff B, Yoshida M, Horinouchi S. Leptomycin B inactivates CRM1/exportin 1 by covalent modification at a cysteine residue in the central conserved region. Proc Natl Acad Sci USA 96: 9112-9117 (1999)
20. Kudo N, Wolff B, Sekimoto T, Schreiner EP, Yoneda Y, Yanagida M, Horinouchi S, Yoshida M. Leptomycin B inhibition of signal-mediated nuclear export by direct binding to CRM1. Exp Cell Res 242: 540-547 (1998)
21. Nishi K, Yoshida M, Fujiwara D, Nishikawa M, Horinouchi S, Beppu T. Leptomycin B targets a regulatory cascade of crm1, a fission yeast nuclear protein, involved in control of higher order chromosome structure and gene expression. J Biol Chem 269: 6320-6324 (1994)
22. Vigneri P, Wang JY. Induction of apoptosis in chronic myelogenous leukemia cells through nuclear entrapment of BCR-ABL tyrosine kinase. Nat Med 7: 228-234 (2001)
23. Ziermann R, Betlach MC. Recombinant polyketide synthesis in Streptomyces: engineering of improved host strains. Biotechniques 26: 106-110 (1999)
24. Kieser T, Bibb MJ, Buttner MJ, Chater KF, Hopwood DA. Practical Streptomyces genetics. (John Innes Centre, Norwich Reseach Park, Colney, Norwich NR4 7UH, England) (2000)
25. Leaf T, Burlingam M, Desai R, Regentin R, Woo E, Ashley G, Licari P. Employing racemic precursors in directed biosynthesis of 6-dEB analogs. J Chem Tech Biotech 77: 1122-1126 (2002)
26. Kao CM, Katz L, Khosla C. Engineered biosynthesis of a complete macrolactone in a heterologous host. Science 265: 509-512 (1994)
27. Kuhstoss S, Rao RN. Analysis of the integration function of the streptomycete bacteriophage φC31. J Mol Biol 222: 897-908 (1991)
28. Kuhstoss S, Richardson MA, Rao RN. Plasmid cloning vectors that integrate site-specifically in Streptomyces spp. Gene 97: 143-146 (1991)
29. Rausch H, Lehmann M. Structural analysis of the actinophage phi C31 attachment site. Nucleic Acids Res 19: 5187-5189 (1991)
30. Hu Z, Pfeifer BA, Chao E, Murli S, Kealey J, Carney JR, Ashley G, Khosla C, Hutchinson CR. A specific role of the Saccharopolyspora erythraea thioesterase II gene in the function of modular polyketide synthases. Microbiology 149: 2213-2225 (2003)
31. Bierman M, Logan R, O'Brien K, Seno ET, Rao RN, Schoner BE. Plasmid cloning vectors for the conjugal transfer of DNA from Escherichia coli to Streptomyces spp. Gene 116: 43-49 (1992)
32. Altschul SF, Gish W, Miller W, Myers EW, Lipman DJ. Basic local alignment search tool. J Mol Biol 215: 403-410 (1990)
33. August PR, Yu TW, Floss HG, Molecular Biological Aspects of Antibiotics Biosynthesis. In Drug Discovery from Nature. Ed., Grabley S, Thiericke R, pp. 215-232, Springer, Jena (1999)
34. Santi DV, Siani MA, Julien B, Kupfer D, Roe B. An approach for obtaining perfect hybridization probes for unknown polyketide synthase genes: a search for the epothilone gene cluster. Gene 247: 97-102 (2000)
35. Bisang C, Long PF, Cortes J, Westcott J, Crosby J, Matharu AL, Cox RJ, Simpson TJ, Staunton J, Leadlay PF. A chain initiation factor common to both modular and aromatic polyketide synthases. Nature 401: 502-505 (1999)
36. Witkowski A, Joshi AK, Lindqvist Y, Smith S. Conversion of a beta-ketoacyl synthase to a malonyl decarboxylase by replacement of the active-site cysteine with glutamine. Biochemistry 38: 11643-11650 (1999)
37. Anderson V, Hammes G. Stereochemistry of the reactions catalyzed by chicken liver fatty acid synthase. Biochemistry 23: 2088-2094 (1984)
38. Chang SI, Hammes GG. Structure and mechanism of a multifunctional enzyme: Fatty acid synthase. Acc Chem Res 23: 363-369(1990)
39. Reid R, Piagentini M, Rodriguez E, Ashley G, Viswanathan N, Carney J, Santi D, Hutchinson C, McDaniel R. A model of structure and catalysis for ketoreductase domains in modular polyketide synthases. Biochemistry 42: 72-79 (2003)
40. Palaniappan N, Kim BS, Sekiyama Y, Osada H, Reynolds KA. Enhancement and selective production of phoslactomycin B, a protein phosphatase IIa inhibitor, through identification and engineering of the corresponding biosynthetic gene cluster. J Biol Chem 278: 35552-35557 (2003)
41. Haydock SF, Aparicio JF, Molnar I, Schwecke T, Khaw LE, Konig A, Marsden AF, Galloway IS, Staunton J, Leadlay PF. Divergent sequence motifs correlated with the substrate specificity of (methyl)malonyl-CoA:acyl carrier protein transacylase domains in modular polyketide synthases. FEBS Lett 374: 246-248 (1995)
42. Kakavas SJ, Katz L, Stassi D. Identification and characterization of the niddamycin polyketide synthase genes from Streptomyces caelestis. J Bacteriol 179: 7515-7522 (1997)
43. Jiralerspong S, Rangaswamy V, Bender CL, Parry RJ. Analysis of the enzymatic domains in the modular portion of the coronafacic acid polyketide synthase. Gene 270: 191-200 (2001)
44. Rangaswamy V, Jiralerspong S, Parry R, Bender CL. Biosynthesis of the Pseudomonas polyketide coronafacic acid requires monofunctional and multifunctional polyketide synthase proteins. Proc Natl Acad Sci USA 95: 15469-15474 (1998)
45. Cundliffe E, Bate N, Butler A, Fish S, Gandecha A, Merson-Davies L. The tylosin-biosynthetic genes of Streptomyces fradiae. Antonie Van Leeuwenhoek 79: 229-234 (2001)
46. Xue Y, Wilson D, Zhao L, Liu H, Sherman DH. Hydroxylation of macrolactones YC-17 and narbomycin is mediated by the pikC-encoded cytochrome P450 in Streptomyces venezuelae. Chem Biol 5: 661-667 (1998).
47. 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: 640-642 (2000)
48. McDaniel R, Ebert-Khosla S, Fu H, Hopwood DA, Khosla C. Engineered biosynthesis of novel polyketides: influence of a downstream enzyme on the catalytic specificity of a minimal aromatic polyketide synthase. Proc Natl Acad Sci USA 91: 11542-11546 (1994)
49. Zhang W, Reynolds KA. MeaA, a putative coenzyme B12-dependent mutase, provides methylmalonyl coenzyme A for monensin biosynthesis in Streptomyces cinnamonensis. J Bacteriol 183: 2071-2080 (2001)
50. Wu K, Chung L, Revill WP, Katz L, Reeves CD. The FK520 gene cluster of Streptomyces hygroscopicus var. ascomyceticus (ATCC 14891) contains genes for biosynthesis of unusual polyketide extender units. Gene 251: 81-90 (2000)
51. Hu Z, Hopwood DA, Hutchinson CR. Enhanced heterologous polyketide production in Streptomyces by exploiting plasmid co-integration. J Ind Microbiol Biotechnol 30: 516-522 (2003)
52. Reid R, Piagentini M, Rodriguez E, Ashley G, Viswanathan N, Carney J, Santi DV, Hutchinson CR, McDaniel R. A model of structure and catalysis for ketoreductase domains in modular polyketide synthases. Biochemistry 42: 72-79 (2003)