A biosynthetic pathway for BE-7585A, a 2-thiosugar-containing angucycline-type natural product

Journal of the American Chemical Society

Volumn 132, Issue 21, 2010, Pages 7405-7417

  Sasaki, Eita ^a,b   Ogasawara, Yasushi ^a,b   Liu, Hung Wen ^a,b  

^a The Center for Molecular Carcinogenesis and Toxicology   (United States)

^b UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BAEYER-VILLIGER; BIOCHEMICAL EXPERIMENTS; BIOCHEMICAL STUDIES; BIOSYNTHETIC PATHWAY; CLONING AND SEQUENCING; DISACCHARIDE UNITS; ESSENTIAL ELEMENTS; FEEDING EXPERIMENTS; GENE CLUSTERS; GLYCOSYL TRANSFERASE; LIVING SYSTEMS; NATURAL PRODUCTS; OPEN READING FRAME; POLYKETIDES; PURIFIED ENZYME; SULFUR INCORPORATION; SYNTHASE GENE; TETRACYCLIC RINGS; UDP-GLUCOSE;

BIOCHEMISTRY; BIOSYNTHESIS; CLONING; ESCHERICHIA COLI; GLUCOSE; SPECTROSCOPIC ANALYSIS; SUGAR (SUCROSE); SULFUR;

EXPERIMENTS;

2 THIOGLUCOSE 6 PHOSPHATE; 2 THIOTREHALOSE 6 PHOSPHATE; 5 THIOMANNOSE; ANGUCYCLINE DERIVATIVE; BE 7585A; CALICHEAMICIN DERIVATIVE; CELESTICETIN; ESPERAMICIN DERIVATIVE; GILVOCARCIN V; GLUCOSE 6 PHOSPHATE; GLUCOSINOLATE; GLYCOSYLTRANSFERASE; GRISEIN; KINAMYCIN; KOTALANOL; LINCOMYCIN; NAMENAMICIN; NATURAL PRODUCT; PD 116198; PHOSPHATE; PROTEIN BEXG2; RHODONOCARDIN; SALACINOL; SB 217452; SHISHIJIMICIN; THIOSUGAR; UNCLASSIFIED DRUG; UNINDEXED DRUG; URDAMYCIN A; URIDINE DIPHOSPHATE GLUCOSE; VINEOMYCIN A;

ARTICLE; BAEYER VILLIGER REACTION; BIOSYNTHESIS; CARBOHYDRATE SYNTHESIS; GENE CLUSTER; NUCLEOTIDE SEQUENCE; OPEN READING FRAME; REACTION ANALYSIS; SPECTROSCOPY;

ACTINOMYCETALES; CLONING, MOLECULAR; GENE ORDER; MULTIGENE FAMILY; THIOSUGARS;

EID: 77952801250     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1014037     Document Type: Article

References (94)

1. Rohr, J. and Thiericke, R. Nat. Prod. Rep. 1992, 9, 103-137
2. Okabe, T., Suda, H., Sato, F., and Okanishi, M. (Banyu Pharmaceutical Co., Ltd., Japan). Jpn. Kokai Tokkyo Koho JP 02-16894 A, 1990.
3. Begley, T. P., Xi, J., Kinsland, C., Taylor, S., and McLafferty, F. Curr. Opin. Chem. Biol. 1999, 3, 623-629
4. Fontecave, M., Ollagnier-de-Choudens, S., and Mulliez, E. Chem. Rev. 2003, 103, 2149-2166
5. Mueller, E. G. Nat. Chem. Biol. 2006, 2, 185-194
6. Kessler, D. FEMS Microbiol. Rev. 2006, 30, 825-840
7. Booker, S. J., Cicchillo, R. M., and Grove, T. L. Curr. Opin. Chem. Biol. 2007, 11, 543-552
8. Jurgenson, C. T., Begley, T. P., and Ealick, S. E. Annu. Rev. Biochem. 2009, 78, 569-603
9. Etoh, H., Iguchi, M., Nagasawa, T., Tani, Y., Yamada, H., and Fukami, H. Agric. Biol. Chem. 1987, 51, 1819-1824
10. Hoeksema, H., Bannister, B., Birkenmeyer, R. D., Kagan, F., Magerlein, B. J., Mackellar, F. A., Schroeder, W., Slomp, G., and Herr, R. R. J. Am. Chem. Soc. 1964, 86, 4223-4224
11. Hoeksema, H. J. Am. Chem. Soc. 1964, 86, 4224-4225
12. Lee, M. D., Dunne, T. S., Siegel, M. M., Chang, C. C., Morton, G. O., and Borders, D. B. J. Am. Chem. Soc. 1987, 109, 3464-3466
13. Golik, J., Clardy, J., Dubay, G., Groenewold, G., Kawaguchi, H., Konishi, M., Krishnan, B., Ohkuma, H., Saitoh, K., and Doyle, T. W. J. Am. Chem. Soc. 1987, 109, 3461-3462
14. McDonald, L. A., Capson, T. L., Krishnamurthy, G., Ding, W.-D., Ellestad, G. A., Bernan, V. S., Maiese, W. M., Lassota, P., Discafani, C., Kramer, R. A., and Ireland, C. M. J. Am. Chem. Soc. 1996, 118, 10898-10899
15. Oku, N., Matsunaga, S., and Fusetani, N. J. Am. Chem. Soc. 2003, 125, 2044-2045
16. Benz, G., Schröder, T., Kurz, J., Wünsche, C., Karl, W., Steffens, G., Pfitzner, J., and Schmidt, D. Angew. Chem., Int. Ed. 1982, 21, 527-528
17. Stefanska, A. L., Fulston, M., Houge-Frydrych, C. S. V., Jones, J. J., and Warr, S. R. J. Antibiot. 2000, 53, 1346-1353
18. Yoshikawa, M., Murakami, T., Yashiro, K., and Matsuda, H. Chem. Pharm. Bull. 1998, 46, 1339-1340
19. Yoshikawa, M., Morikawa, T., Matsuda, H., Tanabe, G., and Muraoka, O. Bioorg. Med. Chem. 2002, 10, 1547-1554
20. Gershenzon, J. and Halkier, B. A. Annu. Rev. Plant Biol. 2006, 57, 303-333
21. Capaon, R. J. and MacLeod, J. K. J. Chem. Soc., Chem. Commun. 1987, 15, 1200-1201
22. Ahlert, J., Shepard, E., Lomovskaya, N., Zazopoulos, E., Staffa, A., Bachmann, B. O., Huang, K., Fonstein, L., Czisny, A., Whitwam, R. E., Farnet, C. M., and Thorson, J. S. Science 2002, 297, 1173-1174
23. Peschke, U., Schmidt, H., Zhang, H.-Z., and Piepersberg, W. Mol. Microbiol. 1995, 16, 1137-1156
24. Ermàk, L., Novotnà, J., Sàgovà- Mareèkovà, M., Kopeck , J., Najmanovà, L., and Janata, J. Folia Microbiol. 2007, 52, 457-462
25. He, X. M. and Liu, H. -w. Annu. Rev. Biochem. 2002, 71, 701-754
26. Thibodeaux, C. J., Melancon, C. E., III., and Liu, H.-w. Nature 2007, 446, 1008-1016
27. Mendez, C., Luzhetskyy, A., Bechthold, A., and Salas, J. A. Curr. Top. Med. Chem. 2008, 8, 710-724
28. Thibodeaux, C. J., Melancon, C. E., III., and Liu, H.-w. Angew. Chem., Int. Ed. 2008, 47, 9814-9859
29. Sambrook, J. and Russell, D. W. Molecular Cloning: A Laboratory Mannual, 3 rd ed.; Cold Spring Harbor Laboratory Press:: Cold Spring Harbor, NY, 2001.
30. Bierman, M., Logan, R., O'Brien, K., Seno, E. T., Nagaraja Rao, R., and Schoner, B. E. Gene 1992, 116, 43-49
31. Han, L., Yang, K., Ramalingam, E., Mosher, R. H., and Vining, L. C. Microbiology 1994, 140, 3379-3389
32. Malpartida, F. and Hopwood, D. A. Nature 1984, 309, 462-464
33. Malpartida, F., Hallam, S. E., Kieser, H. M., Motamedi, H., Hutchinson, C. R., Butler, M. J., Sugden, D. A., Warren, M., McKillop, C., Bailey, C. R., Humphreys, G. O., and Hopwood, D. A. Nature 1987, 325, 818-821
34. Chen, H., Agnihotri, G., Guo, Z., Que, N. L. S., Chen, X., and Liu, H.-w. J. Am. Chem. Soc. 1999, 121, 8124-8125
35. Draeger, G., Park, S.-H., and Floss, H. G. J. Am. Chem. Soc. 1999, 121, 2611-2612
36. Zhang, H., White-Phillip, J. A., Melancon, C. E., III., Kwon, H.-j., Yu, W.-l., and Liu, H.-w. J. Am. Chem. Soc. 2007, 129, 14670-14683
37. Hong, L., Zhao, Z., and Liu, H.-w. J. Am. Chem. Soc. 2006, 128, 14262-14263
38. Hoffmeister, D., Ichinose, K., Domann, S., Faust, B., Trefzer, A., Dräger, G., Kirschning, A., Fischer, C., Künzel, E., Bearden, D. W., Rohr, J., and Bechthold, A. Chem. Biol. 2000, 7, 821-831
39. Westrich, L., Domann, S., Faust, B., Bedford, D., Hopwood, D. A., and Bechthold, A. FEMS Microbiol. Lett. 1999, 381-387
40. Melancon, C. E., III. and Liu, H.-w. J. Am. Chem. Soc. 2007, 129, 4896-4897
41. Ishikawa, J. and Hotta, K. FEMS Microbiol. Lett. 1999, 174, 251-253
42. Bradford, M. M. Anal. Biochem. 1976, 72, 248-254
43. Deferrari, J. O., Gros, E. G., and Mastronardi, I. O. Carbohydr. Res. 1967, 4, 432-434
44. Kovàè, P. Carbohydr. Res. 1986, 153, 168-170
45. Hamacher, K. Carbohydr. Res. 1984, 128, 291-295
46. Pavliak, V. and Kovàè, P. Carbohydr. Res. 1991, 210, 333-337
47. Kirk, B. A. and Knapp, S. Tetrahedron Lett. 2003, 44, 7601-7605
48. Knapp, S., Naughton, A. B. J., Jaramillo, C., and Pipik, B. J. Org. Chem. 1992, 57, 7328-7334
49. See Supporting Information.
50. Hertweck, C., Luzhetskyy, A., Rebets, Y., and Bechthold, A. Nat. Prod. Rep. 2007, 24, 162-190
51. Rohr, J. J. Antibiot. 1989, 42, 1151-1157
52. Tanaka, H. and Omura, S. J. Antibiot. 1982, 35, 602-608
53. Gould, S. J., Cheng, X. C., and Halley, K. A. J. Am. Chem. Soc. 1992, 114, 10066-10068
54. Sato, Y., Geckle, M., and Gould, S. J. Tetrahedron Lett. 1985, 26, 4023-4026
55. Sato, Y. and Gould, S. J. J. Am. Chem. Soc. 1986, 108, 4625-4631
56. Seaton, P. J. and Gould, S. J. J. Am. Chem. Soc. 1987, 109, 5282-5284
57. Takahashi, K. and Tomita, F. J. Antibiot. 1983, 36, 1531-1535
58. Carter, G. T., Fantini, A. A., James, J. C., Borders, D. B., and White, R. J. J. Antibiot. 1985, 38, 242-248
59. Gould, S. J. and Halley, K. A. J. Am. Chem. Soc. 1991, 113, 5092-5093
60. Liu, T., Fischer, C., Beninga, C., and Rohr, J. J. Am. Chem. Soc. 2004, 126, 12262-12263
61. Rix, U., Wang, C., Chen, Y., Lipata, F. M., Rix, L. L. R., Greenwell, L. M., Vining, L. C., Yang, K., and Rohr, J. ChemBioChem 2005, 6, 838-845
62. Gibson, M., Nur-e-alam, M., Lipata, F., Oliveira, M. A., and Rohr, J. J. Am. Chem. Soc. 2005, 127, 17594-17595
63. Beam, M. P., Bosserman, M. A., Noinaj, N., Wehenkel, M., and Rohr, J. Biochemistry 2009, 48, 4476-4487
64. Drautz, H., Zähner, H., Rohr, J., and Zeeck, A. J. Antibiot. 1986, 12, 1657-1669
65. Decker, H. and Haag, S. J. Bacteriol. 1995, 177, 6126-6136
66. Faust, B., Hoffmeister, D., Weitnauer, G., Westrich, L., Haag, S., Schneider, P., Decker, H., Künzel, E., Rohr, J., and Bechthold, A. Microbiology 2000, 146, 147-154
67. Fischer, C., Lipata, F., and Rohr, J. J. Am. Chem. Soc. 2003, 125, 7818-7819
68. Kharel, M. K., Zhu, L., Liu, T., and Rohr, J. J. Am. Chem. Soc. 2007, 129, 3780-3781
69. Gould, S. and Cheng, X. C. J. Org. Chem. 1994, 59, 400-405
70. Wang, L., McVey, J., and Vining, L. C. Microbiology 2001, 147, 1535-1545
71. Räty, K., Kunnari, T., Hakala, J., Mäntsälä, P., and Ylihonko, K. Mol. Gen. Genet. 2000, 264, 164-172
72. Ichinose, K., Bedford, D. J., Tornus, D., Bechthold, A., Bibb, M. J., Revill, W. P., Floss, H. G., and Hopwood, D. A. Chem. Biol. 1998, 5, 647-659
73. Olano, C., Gómez, C., Pérez, M., Palomino, M., Pineda-Lucena, A., Carbajo, R. J., Braña, A. F., Méndez, C., and Salas, J. A. Chem. Biol. 2009, 16, 1031-1044
74. Thorson, J. S. and Liu, H.-w. J. Am. Chem. Soc. 1993, 115, 7539-7540
75. Hallis, T. M. and Liu, H.-w. Acc. Chem. Res. 1999, 32, 579-588
76. He, X., Agnihotri, G., and Liu, H.-w. Chem. Rev. 2000, 100, 4615-4661
77. Hong, L., Zhao, Z., Melanμon, C. E., III., Zhang, H., and Liu, H.-w. J. Am. Chem. Soc. 2008, 130, 4954-4967
78. Chang, S., Duerr, B., and Serif, G. J. Biol. Chem. 1988, 263, 1693-1697
79. Alam, J., Beyer, N., and Liu, H.-w. Biochemistry 2004, 43, 16450-16460
80. Trefzer, A., Hoffmeister, D., Künzel, E., Stockert, S., Weitnauer, G., Westrich, L., Rix, U., Fuchser, J., Bindseil, K. U., Rohr, J., and Bechthold, A. Chem. Biol. 2000, 7, 133-142
81. Schuman, B., Alfaro, J. A., and Evans, S. V. Top. Curr. Chem. 2007, 272, 217-257
82. Begley, T. P. Nat. Prod. Rep. 2006, 23, 15-25
83. Settembre, E. C., Dorrestein, P. C., Zhai, H., Chatterjee, A., McLafferty, F. W., Begley, T. P., and Ealick, S. E. Biochemistry 2004, 43, 11647-11657
84. Xi, J., Ge, Y., Kinsland, C., McLafferty, F. W., and Begley, T. P. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 8513-8518
85. Lehmann, C., Begley, T. P., and Ealick, S. E. Biochemistry 2006, 45, 11-19
86. Avonce, N., Mendoza-Vargas, A., Morett, E., and Iturriaga, G. BMC Evol. Biol. 2006, 6, 109
87. Ikeda, H., Ishikawa, J., Hanamoto, A., Shinose, M., Kikuchi, H., Shiba, T., Sakaki, Y., Hattori, M., and Omura, S. Nat. Biotechnol. 2003, 21, 526-531
88. Oliynyk, M., Samborskyy, M., Lester, J. B., Mironenko, T., Scott, N., Dickens, S., Haydock, S. F., and Leadlay, P. F. Nat. Biotechnol. 2007, 25, 447-453
89. Qu, Q., Lee, S.-J., and Boos, W. J. Biol. Chem. 2004, 279, 47890-47897
90. Ryu, S.-I., Park, C.-S., Cha, J., Woo, E.-J., and Lee, S.-B. Biochem. Biophys. Res. Commun. 2005, 329, 429-436
91. Kouril, T., Zaparty, M., Marrero, J., Brinkmann, H., and Siebers, B. Arch. Microbiol. 2008, 190, 355-369
92. Nobre, A., Alarico, S., Fernandes, C., Empadinhas, N., and da Costa, M. S. J. Bacteriol. 2008, 190, 7939-7946
93. Rohr, J. J. Chem. Soc., Chem. Commun. 1989, 8, 492-493
94. Walsh, C. Nature 2000, 406, 775-781