An Enzyme Catalyzing O-Prenylation of the Glucose Moiety of Fusicoccin A, a Diterpene Glucoside Produced by the Fungus Phomopsis amygdali

ChemBioChem

Volumn 13, Issue 4, 2012, Pages 566-573

  Noike, Motoyoshi ^a   Liu, Chengwei ^a   Ono, Yusuke ^a   Hamano, Yoshimitsu ^b   Toyomasu, Tomonobu ^c   Sassa, Takeshi ^c   Kato, Nobuo ^d   Dairi, Tohru ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b FUKUI PREFECTURAL UNIVERSITY   (Japan)

^c YAMAGATA UNIVERSITY   (Japan)

^d OSAKA UNIVERSITY   (Japan)

Author keywords

Biosynthesis; Fungi; Fusicoccin; Prenyltransferases; Terpenoids

Indexed keywords

DIMETHYLALLYL DIPHOSPHATE; DIMETHYLALLYLTRANSFERASE; DIVALENT CATION; FUSICOCCIN; FUSICOCCIN A; GERANYLGERANYL PYROPHOSPHATE; GLUCOSE; MONOMER; PYROPHOSPHATE; RECOMBINANT ENZYME; SUGAR; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CONTROLLED STUDY; COVALENT BOND; ENZYME ACTIVITY; FUNGAL GENE; FUNGAL GENOME; FUNGUS; GENETIC DATABASE; IN VITRO STUDY; NONHUMAN; PHOMOPSIS AMYGDALI; PRENYLATION; PRIORITY JOURNAL;

ASCOMYCOTA; BIOCATALYSIS; DIMETHYLALLYLTRANSTRANSFERASE; GLUCOSE; GLYCOSIDES; KINETICS; MOLECULAR CONFORMATION; PRENYLATION; SUBSTRATE SPECIFICITY;

ACTINOBACTERIA; FUNGI; PHOMOPSIS AMYGDALI;

EID: 84863261905     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.201100725     Document Type: Article

References (55)

1. D. W. Christianson, Science 2007, 316, 60-61.
2. J. D. Connolly, R. A. Hill, Dictionary of Terpenoids, Chapman and Hall, New York, 1992.
3. P. M. Dewick, Nat. Prod. Rep. 2002, 19, 181-222.
4. B. H. Wang, B. Ternai, G. Polya, Phytochemistry 1997, 44, 787-796.
5. M. Maitrejean, G. Comte, D. Barron, K. El Kirat, G. Conseil, A. Di Pietro, Bioorg. Med. Chem. Lett. 2000, 10, 157-160.
6. A. Murakami, G. Gao, M. Omura, M. Yano, C. Ito, H. Furukawa, D. Takahashi, K. Koshimizu, H. Ohigashi, Bioorg. Med. Chem. Lett. 2000, 10, 59-62.
7. K. Komiyama, S. Funayama, Y. Anraku, M. Ishibashi, Y. Takahashi, S. Omura, J. Antibiot. 1990, 43, 247-252.
8. K. Shin-ya, S. Imai, K. Furihata, Y. Hayakawa, Y. Kato, G. D. Vanduyne, J. Clardy, H. Seto, J. Antibiot. 1990, 43, 444-447.
9. C. Pathirana, P. R. Jensen, W. Fenical, Tetrahedron Lett. 1992, 33, 7663-7666.
10. K. Shiomi, H. Nakamura, H. Iinuma, H. Naganawa, K. Isshiki, T. Takeuchi, H. Umezawa, Y. Iitaka, J. Antibiot. 1986, 39, 494-501.
11. L. Heide, Curr. Opin. Chem. Biol. 2009, 13, 171-179.
12. F. Pojer, E. Wemakor, B. Kammerer, H. Chen, C. T. Walsh, S.-M. Li, L. Heide, Proc. Natl. Acad. Sci. USA 2003, 100, 2316-2321.
13. T. Kuzuyama, J. P. Noel, S. B. Richard, Nature 2005, 435, 983-987.
14. T. Ozaki, S. Mishima, M. Nishiyama, T. Kuzuyama, J. Antibiot. 2009, 62, 385-392.
15. Y. Haagen, I. Unsöld, L. Westrich, B. Gust, S. B. Richard, J. P. Noel, L. Heide, FEBS Lett. 2007, 581, 2889-2893.
16. T. Kumano, S. B. Richard, J. P. Noel, M. Nishiyama, T. Kuzuyama, Bioorg. Med. Chem. 2008, 16, 8117-8126.
17. E. Haug-Schifferdecker, D. Arican, R. Brückner, L. Heide, J. Biol. Chem. 2010, 285, 16487-16494.
18. H. F. Tsai, H. Wang, J. C. Gebler, C. D. Poulter, C. L. Schardl, Biochem. Biophys. Res. Commun. 1995, 216, 119-125.
19. I. A. Unsöld, S.-M. Li, Microbiology 2005, 151, 1499-1505.
20. I. A. Unsöld, S.-M. Li, ChemBioChem 2006, 7, 158-164.
21. A. Grundmann, S.-M. Li, Microbiology 2005, 151, 2199-2207.
22. A. Grundmann, T. Kuznetsova, S. Sh. Afiyatullov, S.-M. Li, ChemBioChem 2008, 9, 2059-2063.
23. A. Kremer, L. Westrich, S.-M. Li, Microbiology 2007, 153, 3409-3416.
24. W.-B. Yin, H.-L. Ruan, L. Westrich, A. Grundmann, S.-M. Li, ChemBioChem 2007, 8, 1154-1161.
25. W.-B. Yin, A. Grundmann, J. Cheng, S.-M. Li, J. Biol. Chem. 2009, 284, 100-109.
26. C. J. Balibar, A. R. Howard-Jones, C. T. Walsh, Nat. Chem. Biol. 2007, 3, 584-592.
27. Y. Ding, R. M. Williams, D. H. Sherman, J. Biol. Chem. 2008, 283, 16068-16076.
28. A. Kremer, S.-M. Li, Microbiology 2010, 156, 278-286.
29. W.-B. Yin, X. Yu, X.-L. Xie, S.-M. Li, Org. Biomol. Chem. 2010, 8, 2430-2438.
30. H.-X. Zou, X.-L. Xie, U. Linne, X.-D. Zheng, S.-M. Li, Org. Biomol. Chem. 2010, 8, 3037-3044.
31. X. Liu, C. T. Walsh, Biochemistry 2009, 48, 11032-11044.
32. D. J. Edwards, W. H. Gerwick, J. Am. Chem. Soc. 2004, 126, 11432-11433.
33. S. Takahashi, H. Takagi, A. Toyoda, M. Uramoto, T. Nogawa, M. Ueki, Y. Sakaki, H. Osada, J. Bacteriol. 2010, 192, 2839-2851.
34. M. N. Ashby, S. Y. Kutsunai, S. Ackerman, A. Tzagoloff, P. A. Edwards, J. Biol. Chem. 1992, 267, 4128-4136.
35. K. Yazaki, M. Kunihisa, T. Fujisaki, F. Sato, J. Biol. Chem. 2002, 277, 6240-6246.
36. K. Sasaki, K. Mito, K. Ohara, H. Yamamoto, K. Yazaki, Plant Physiol. 2008, 146, 1075-1084.
37. K. Sasaki, Y. Tsurumaru, H. Yamamoto, K. Yazaki, J. Biol. Chem. 2011, 286, 24125-24134.
38. M. M. Bradford, Anal. Biochem. 1976, 72, 248-254.
39. N. Tajima, H. Kume, S. Kanematsu, N. Kato, T. Sassa, J. Pesticide Sci. 2002, 27, 64-67.
40. T. Sassa, N. Tajima, M. Sato, A. Takahashi, N. Kato, Biosci. Biotechnol. Biochem. 2002, 66, 2356-2361.
41. K. D. Barrow, D. H. R. Barton, E. Chain, U. F. W. Ohnsorge, R. P. Sharma, J. Chem. Soc. Perkin Trans. 1 1973, 15, 1590-1599.
42. T. Toyomasu, M. Tsukahara, A. Kaneko, R. Niida, W. Mitsuhashi, T. Dairi, N. Kato, T. Sassa, Proc. Natl. Acad. Sci. USA 2007, 104, 3084-3088.
43. A. Minami, N. Tajima, Y. Higuchi, T. Toyomasu, T. Sassa, N. Kato, T. Dairi, Bioorg. Med. Chem. Lett. 2009, 19, 870-874.
44. M. Hashimoto, Y. Higuchi, S. Takahashi, H. Osada, T. Sakaki, T. Toyomasu, T. Sassa, N. Kato, T. Dairi, Bioorg. Med. Chem. Lett. 2009, 19, 5640-5643.
45. L. C. Tarshis, M. Yan, C. D. Poulter, J. C. Sacchettini, Biochemistry 1994, 33, 10871-10877.
46. T. Koyama, M. Tajima, H. Sano, T. Doi, A. Koike-Takeshita, S. Obata, T. Nishino, K. Ogura, Biochemistry 1996, 35, 9533-9538.
47. P. Schneider, M. Weber, D. Hoffmeister, Fungal Genet. Biol. 2008, 45, 302-309.
48. K. D. Barrow, D. H. R. Barton, E. Chain, D. Bageenda-Kasujja, G. Mellows, J. Chem. Soc. Perkin Trans. 1 1975, 17, 877-883.
49. X. Yu, X. Xie, S.-M. Li, Appl. Microbiol. Biotechnol. 2011, 92, 737-748.
50. U. Metzger, C. Schall, G. Zocher, I. Unsöld, E. Stec, S.-M. Li, L. Heide, T. Stehle, Proc. Natl. Acad. Sci. USA 2009, 106, 14309-14314.
51. M. Jost, G. Zocher, S. Tarcz, M. Matuschek, X. Xie, S.-M. Li, T. Stehle, J. Am. Chem. Soc. 2010, 132, 17849-17858.
52. T. Ishikawa, Y. Sega, J. Kitajima, Chem. Pharm. Bull. 2001, 49, 840-844.
53. Y. Takeda, K. Yano, H. Ayabe, T. Masuda, H. Otsuka, E. Sueyoshi, T. Shinzato, M. Aramoto, J. Nat. Med. 2008, 62, 476-478.
54. V. Costantino, E. Fattorusso, A. Mangoni, M. Di Rosa, A. Ianaro, Bioorg. Med. Chem. Lett. 1999, 9, 271-276.
55. J. D. Thompson, D. G. Higgins, T. J. Gibson, Nucleic Acids Res. 1994, 22, 4673-4680.