SCOPUS 정보 검색 플랫폼

Volumn 16, Issue 5, 2015, Pages 772-781

Identification of a new diterpene biosynthetic gene cluster that produces O-methylkolavelool in herpetosiphon aurantiacus

(4) Nakano, Chiaki a Oshima, Misaki a Kurashima, Nodoka a Hoshino, Tsutomu a

a NIIGATA UNIVERSITY (Japan)

Author keywords

diterpene cyclases; diterpene synthases; Herpetosiphon aurantiacus; natural products; terpenoids

Indexed keywords

CARBON; CATION; DITERPENE; DITERPENOID; DNA FRAGMENT; GERANYLGERANYL PYROPHOSPHATE; KOLAVELOOL; KOLAVENYL DIPHOSPHATE; O METHYLKOLAVELOOL; PHOSPHATE; RECOMBINANT PROTEIN; UNCLASSIFIED DRUG; WATER; METHYLTRANSFERASE; O-METHYLKOLAVELOOL;

AMINO ACID SEQUENCE; ARTICLE; BACTERIAL STRAIN; BIOSYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; ENZYME ASSAY; ESCHERICHIA COLI; GAS CHROMATOGRAPHY; GENE CLUSTER; HERPETOSIPHON; HERPETOSIPHON AURANTIACUS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; IN VIVO STUDY; MASS SPECTROMETRY; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PLASMID; POLYACRYLAMIDE GEL ELECTROPHORESIS; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTON NUCLEAR MAGNETIC RESONANCE; SEQUENCE HOMOLOGY; CHEMISTRY; CHLOROFLEXI; CONFORMATION; CYTOLOGY; GENETICS; METABOLISM; MULTIGENE FAMILY;

FUNGI; HERPETOSIPHON AURANTIACUS; HERPETOSIPHON AURANTIACUS ATCC 23779; MYCOBACTERIUM TUBERCULOSIS; PUFFINUS AURICULARIS;

CHLOROFLEXI; DITERPENES; METHYLTRANSFERASES; MOLECULAR CONFORMATION; MULTIGENE FAMILY;

EID: 84924901774 PISSN: 14394227 EISSN: 14397633 Source Type: Journal
DOI: 10.1002/cbic.201402652 Document Type: Article

Times cited : (29)

References (50)

1
- 33748601470
- D. W. Christianson, Chem. Rev. 2006, 106, 3412-3442.
- (2006) Chem. Rev. , vol.106 , pp. 3412-3442
- Christianson, D.W.¹

2
- 43049107992
- D. W. Christianson, Curr. Opin. Chem. Biol. 2008, 12, 141-150.
- (2008) Curr. Opin. Chem. Biol. , vol.12 , pp. 141-150
- Christianson, D.W.¹

3
- 84856158159
- E. Oldfield, F.-Y. Lin, Angew. Chem. Int. Ed. 2012, 51, 1124-1137
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 1124-1137
- Oldfield, E.¹ Lin, F.-Y.²

4
- 84892678140
- Angew. Chem. 2012, 124, 1150-1163.
- (2012) Angew. Chem. , vol.124 , pp. 1150-1163

5
- 77955822715
- R. Cao, Y. Zhang, F. M. Mann, C. Huang, D. Mukkamala, M. P. Hudock, M. E. Mead, S. Prisic, K. Wang, F.-Y. Lin, T.-K. Chang, R. J. Peters, E. Oldfield, Proteins Struct. Funct. Bioinf. 2010, 78, 2417-2432.
- (2010) Proteins Struct. Funct. Bioinf. , vol.78 , pp. 2417-2432
- Cao, R.¹ Zhang, Y.² Mann, F.M.³ Huang, C.⁴ Mukkamala, D.⁵ Hudock, M.P.⁶ Mead, M.E.⁷ Prisic, S.⁸ Wang, K.⁹ Lin, F.-Y.¹⁰ Chang, T.-K.¹¹ Peters, R.J.¹² Oldfield, E.¹³

6
- 84862782999
- M. J. Smanski, R. M. Peterson, S.-X. Huang, B. Shen, Curr. Opin. Chem. Biol. 2012, 16, 132-141.
- (2012) Curr. Opin. Chem. Biol. , vol.16 , pp. 132-141
- Smanski, M.J.¹ Peterson, R.M.² Huang, S.-X.³ Shen, B.⁴

7
- 84924907360
- H.-Y. Gong, Y. Zeng, X.-Y. Chen, Nat. Prod. Bioprospect. 2014, 4, 59-72.
- (2014) Nat. Prod. Bioprospect. , vol.4 , pp. 59-72
- Gong, H.-Y.¹ Zeng, Y.² Chen, X.-Y.³

8
- 0034810693
- T. Dairi, Y. Hamano, T. Kuzuyama, N. Itoh, K. Furihata, H. Seto, J. Bacteriol. 2001, 183, 6085-6094.
- (2001) J. Bacteriol. , vol.183 , pp. 6085-6094
- Dairi, T.¹ Hamano, Y.² Kuzuyama, T.³ Itoh, N.⁴ Furihata, K.⁵ Seto, H.⁶

9
- 0037020261
- Y. Hamano, T. Kuzuyama, N. Itoh, K. Furihata, H. Seto, T. Dairi, J. Biol. Chem. 2002, 277, 37098-37104.
- (2002) J. Biol. Chem. , vol.277 , pp. 37098-37104
- Hamano, Y.¹ Kuzuyama, T.² Itoh, N.³ Furihata, K.⁴ Seto, H.⁵ Dairi, T.⁶

10
- 10044297112
- T. Kawasaki, T. Kuzuyama, Y. Kuwamori, N. Matsuura, N. Itoh, K. Furihata, H. Seto, T. Dairi, J. Antibiot. 2004, 57, 739-747.
- (2004) J. Antibiot. , vol.57 , pp. 739-747
- Kawasaki, T.¹ Kuzuyama, T.² Kuwamori, Y.³ Matsuura, N.⁴ Itoh, N.⁵ Furihata, K.⁶ Seto, H.⁷ Dairi, T.⁸

11
- 32444437181
- T. Kawasaki, Y. Hayashi, T. Kuzuyama, K. Furihata, N. Itoh, H. Seto, T. Dairi, J. Bacteriol. 2006, 188, 1236-1244.
- (2006) J. Bacteriol. , vol.188 , pp. 1236-1244
- Kawasaki, T.¹ Hayashi, Y.² Kuzuyama, T.³ Furihata, K.⁴ Itoh, N.⁵ Seto, H.⁶ Dairi, T.⁷

12
- 34147203208
- C. Ikeda, Y. Hayashi, N. Itoh, H. Seto, T. Dairi, J. Biochem. 2007, 141, 37-45.
- (2007) J. Biochem. , vol.141 , pp. 37-45
- Ikeda, C.¹ Hayashi, Y.² Itoh, N.³ Seto, H.⁴ Dairi, T.⁵

13
- 67651112019
- S.-Y. Kim, P. Zhao, M. Igarashi, R. Sawa, T. Tomita, M. Nishiyama, T. Kuzuyama, Chem. Biol. 2009, 16, 736-743.
- (2009) Chem. Biol. , vol.16 , pp. 736-743
- Kim, S.-Y.¹ Zhao, P.² Igarashi, M.³ Sawa, R.⁴ Tomita, T.⁵ Nishiyama, M.⁶ Kuzuyama, T.⁷

14
- 84873496322
- A. Meguro, T. Tomita, M. Nishiyama, T. Kuzuyama, ChemBioChem 2013, 14, 316-321.
- (2013) ChemBioChem , vol.14 , pp. 316-321
- Meguro, A.¹ Tomita, T.² Nishiyama, M.³ Kuzuyama, T.⁴

15
- 58149507674
- D. Morrone, J. Chambers, L. Lowry, G. Kim, A. Anterola, K. Bender, R. J. Peters, FEBS Lett. 2009, 583, 475-480.
- (2009) FEBS Lett. , vol.583 , pp. 475-480
- Morrone, D.¹ Chambers, J.² Lowry, L.³ Kim, G.⁴ Anterola, A.⁵ Bender, K.⁶ Peters, R.J.⁷

16
- 33646052859
- C. Dürr, H.-J. Schnell, A. Luzhetskyy, R. Murillo, M. Weber, K. Welzel, A. Vente, A. Bechthold, Chem. Biol. 2006, 13, 365-377.
- (2006) Chem. Biol. , vol.13 , pp. 365-377
- Dürr, C.¹ Schnell, H.-J.² Luzhetskyy, A.³ Murillo, R.⁴ Weber, M.⁵ Welzel, K.⁶ Vente, A.⁷ Bechthold, A.⁸

17
- 54049115940
- Y. Hayashi, N. Matsuura, H. Toshima, N. Itoh, J. Ishikawa, Y. Mikami, T. Dairi, J. Antibiot. 2008, 61, 164-174.
- (2008) J. Antibiot. , vol.61 , pp. 164-174
- Hayashi, Y.¹ Matsuura, N.² Toshima, H.³ Itoh, N.⁴ Ishikawa, J.⁵ Mikami, Y.⁶ Dairi, T.⁷

18
- 80051997249
- M. J. Smanski, Z. Yu, J. Casper, S. Lin, R. M. Peterson, Y. Chen, E. Wendt-Pienkowski, S. R. Rajski, B. Shen, Proc. Natl. Acad. Sci. USA 2011, 108, 13498-13503.
- (2011) Proc. Natl. Acad. Sci. USA , vol.108 , pp. 13498-13503
- Smanski, M.J.¹ Yu, Z.² Casper, J.³ Lin, S.⁴ Peterson, R.M.⁵ Chen, Y.⁶ Wendt-Pienkowski, E.⁷ Rajski, S.R.⁸ Shen, B.⁹

19
- 84908611137
- M. Xu, M. L. Hillwig, A. L. Lane, M. S. Tiernan, B. S. Moore, R. J. Peters, J. Nat. Prod. 2014, 77, 2144-2147.
- (2014) J. Nat. Prod. , vol.77 , pp. 2144-2147
- Xu, M.¹ Hillwig, M.L.² Lane, A.L.³ Tiernan, M.S.⁴ Moore, B.S.⁵ Peters, R.J.⁶

20
- 84896869513
- P. Xie, M. Ma, M. E. Rateb, K. A. Shaaban, Z. Yu, S.-X. Huang, L.-X. Zhao, X. Zhu, Y. Yan, R. M. Peterson, J. R. Lohman, D. Yang, M. Yin, J. D. Rudolf, Y. Jiang, Y. Duan, B. Shen, J. Nat. Prod. 2014, 77, 377-387.
- (2014) J. Nat. Prod. , vol.77 , pp. 377-387
- Xie, P.¹ Ma, M.² Rateb, M.E.³ Shaaban, K.A.⁴ Yu, Z.⁵ Huang, S.-X.⁶ Zhao, L.-X.⁷ Zhu, X.⁸ Yan, Y.⁹ Peterson, R.M.¹⁰ Lohman, J.R.¹¹ Yang, D.¹² Yin, M.¹³ Rudolf, J.D.¹⁴ Jiang, Y.¹⁵ Duan, Y.¹⁶ Shen, B.¹⁷

21
- 14944348414
- C. Nakano, T. Okamura, T. Sato, T. Dairi, T. Hoshino, Chem. Commun. 2005, 1016-1018.
- (2005) Chem. Commun. , pp. 1016-1018
- Nakano, C.¹ Okamura, T.² Sato, T.³ Dairi, T.⁴ Hoshino, T.⁵

22
- 70349546277
- C. Nakano, T. Hoshino, ChemBioChem 2009, 10, 2060-2071.
- (2009) ChemBioChem , vol.10 , pp. 2060-2071
- Nakano, C.¹ Hoshino, T.²

23
- 78951494772
- C. Nakano, T. Ootsuka, K. Takayama, T. Mitsui, T. Sato, T. Hoshino, Biosci. Biotechnol. Biochem. 2011, 75, 75-81.
- (2011) Biosci. Biotechnol. Biochem. , vol.75 , pp. 75-81
- Nakano, C.¹ Ootsuka, T.² Takayama, K.³ Mitsui, T.⁴ Sato, T.⁵ Hoshino, T.⁶

24
- 79952749923
- T. Hoshino, C. Nakano, T. Ootsuka, Y. Shinohara, T. Hara, Org. Biomol. Chem. 2011, 9, 2156-2165.
- (2011) Org. Biomol. Chem. , vol.9 , pp. 2156-2165
- Hoshino, T.¹ Nakano, C.² Ootsuka, T.³ Shinohara, Y.⁴ Hara, T.⁵

25
- 10044261867
- A. Rudi, M. Aknin, E. Gaydou, Y. Kashman, J. Nat. Prod. 2004, 67, 1932-1935.
- (2004) J. Nat. Prod. , vol.67 , pp. 1932-1935
- Rudi, A.¹ Aknin, M.² Gaydou, E.³ Kashman, Y.⁴

26
- 4544346542
- K. Pethe, D. L. Swenson, S. Alonso, J. Anderson, C. Wang, D. G. Russell, Proc. Natl. Acad. Sci. USA 2004, 101, 13642-13647.
- (2004) Proc. Natl. Acad. Sci. USA , vol.101 , pp. 13642-13647
- Pethe, K.¹ Swenson, D.L.² Alonso, S.³ Anderson, J.⁴ Wang, C.⁵ Russell, D.G.⁶

27
- 72249095195
- F. M. Mann, M. Xu, X. Chen, D. B. Fulton, D. G. Russell, R. J. Peters, J. Am. Chem. Soc. 2009, 131, 17526-17527.
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 17526-17527
- Mann, F.M.¹ Xu, M.² Chen, X.³ Fulton, D.B.⁴ Russell, D.G.⁵ Peters, R.J.⁶

28
- 80054873894
- H. Kiss, M. Nett, N. Domin, K. Martin, J. A. Maresca, A. Copeland, A. Lapidus, S. Lucas, K. W. Berry, T. Glavina Del Rio, E. Dalin, H. Tice, S. Pitluck, P. Richardson, D. Bruce, L. Goodwin, C. Han, J. C. Detter, J. Schmutz, T. Brettin, M. Land, L. Hauser, N. C. Kyrpides, N. Ivanova, M. Göker, T. Woyke, H.-P. Klenk, D. A. Bryant, Stand. Genomic Sci. 2011, 5, 356-370.
- (2011) Stand. Genomic Sci. , vol.5 , pp. 356-370
- Kiss, H.¹ Nett, M.² Domin, N.³ Martin, K.⁴ Maresca, J.A.⁵ Copeland, A.⁶ Lapidus, A.⁷ Lucas, S.⁸ Berry, K.W.⁹ Glavina Del Rio, T.¹⁰ Dalin, E.¹¹ Tice, H.¹² Pitluck, S.¹³ Richardson, P.¹⁴ Bruce, D.¹⁵ Goodwin, L.¹⁶ Han, C.¹⁷ Detter, J.C.¹⁸ Schmutz, J.¹⁹ Brettin, T.²⁰ more..

29
- 0028793115
- T. Yasukawa, C. Kanei-Ishii, T. Maekawa, J. Fujimoto, T. Yamamoto, S. Ishii, J. Biol. Chem. 1995, 270, 25328-25331.
- (1995) J. Biol. Chem. , vol.270 , pp. 25328-25331
- Yasukawa, T.¹ Kanei-Ishii, C.² Maekawa, T.³ Fujimoto, J.⁴ Yamamoto, T.⁵ Ishii, S.⁶

30
- 0028604579
- A. Ohsaki, L. T. Yan, S. Ito, H. Edatsugi, D. Iwata, Y. Komoda, Bioorg. Med. Chem. Lett. 1994, 4, 2889-2892.
- (1994) Bioorg. Med. Chem. Lett. , vol.4 , pp. 2889-2892
- Ohsaki, A.¹ Yan, L.T.² Ito, S.³ Edatsugi, H.⁴ Iwata, D.⁵ Komoda, Y.⁶

31
- 77957965766
- A. Sawabe, K. Minemoto, S. Ouchi, T. Okamoto, J. Jpn. Oil Chem. Soc. 1999, 48, 139-142.
- (1999) J. Jpn. Oil Chem. Soc. , vol.48 , pp. 139-142
- Sawabe, A.¹ Minemoto, K.² Ouchi, S.³ Okamoto, T.⁴

32
- 0026471537
- E. Piers, J. Y. Roberge, Tetrahedron Lett. 1992, 33, 6923-6926.
- (1992) Tetrahedron Lett. , vol.33 , pp. 6923-6926
- Piers, E.¹ Roberge, J.Y.²

33
- 0034762914
- F. Nagashima, M. Suzuki, S. Takaoka, Y. Asakawa, J. Nat. Prod. 2001, 64, 1309-1317.
- (2001) J. Nat. Prod. , vol.64 , pp. 1309-1317
- Nagashima, F.¹ Suzuki, M.² Takaoka, S.³ Asakawa, Y.⁴

34
- 78049311312
- R. J. Peters, Nat. Prod. Rep. 2010, 27, 1521-1530.
- (2010) Nat. Prod. Rep. , vol.27 , pp. 1521-1530
- Peters, R.J.¹

35
- 0037999877
- T. Eguchi, Y. Dekishima, Y. Hamano, T. Dairi, H. Seto, K. Kakinuma, J. Org. Chem. 2003, 68, 5433-5438.
- (2003) J. Org. Chem. , vol.68 , pp. 5433-5438
- Eguchi, T.¹ Dekishima, Y.² Hamano, Y.³ Dairi, T.⁴ Seto, H.⁵ Kakinuma, K.⁶

36
- 34250679269
- S. Prisic, R. J. Peters, Plant Physiol. 2007, 144, 445-454.
- (2007) Plant Physiol. , vol.144 , pp. 445-454
- Prisic, S.¹ Peters, R.J.²

37
- 79959374838
- M. Köksal, H. Hu, R. M. Coates, R. J. Peters, D. W. Christianson, Nat. Chem. Biol. 2011, 7, 431-433.
- (2011) Nat. Chem. Biol. , vol.7 , pp. 431-433
- Köksal, M.¹ Hu, H.² Coates, R.M.³ Peters, R.J.⁴ Christianson, D.W.⁵

38
- 84885074387
- M. Köksal, K. Potter, R. J. Peters, D. W. Christianson, Biochim. Biophys. Acta Gen. Subj. 2014, 1840, 184-190.
- (2014) Biochim. Biophys. Acta Gen. Subj. , vol.1840 , pp. 184-190
- Köksal, M.¹ Potter, K.² Peters, R.J.³ Christianson, D.W.⁴

39
- 84894434236
- H.-C. Chan, X. Feng, T.-P. Ko, C.-H. Huang, Y. Hu, Y. Zheng, S. Bogue, C. Nakano, T. Hoshino, L. Zhang, P. Lv, W. Liu, D. C. Crick, P.-H. Liang, A. H.-J. Wang, E. Oldfield, R.-T. Guo, J. Am. Chem. Soc. 2014, 136, 2892-2896.
- (2014) J. Am. Chem. Soc. , vol.136 , pp. 2892-2896
- Chan, H.-C.¹ Feng, X.² Ko, T.-P.³ Huang, C.-H.⁴ Hu, Y.⁵ Zheng, Y.⁶ Bogue, S.⁷ Nakano, C.⁸ Hoshino, T.⁹ Zhang, L.¹⁰ Lv, P.¹¹ Liu, W.¹² Crick, D.C.¹³ Liang, P.-H.¹⁴ Wang, A.H.-J.¹⁵ Oldfield, E.¹⁶ Guo, R.-T.¹⁷

40
- 84862024512
- K.-H. Teng, P.-H. Liang, Bioorg. Chem. 2012, 43, 51-57.
- (2012) Bioorg. Chem. , vol.43 , pp. 51-57
- Teng, K.-H.¹ Liang, P.-H.²

41
- 84896847440
- E. Layre, H. J. Lee, D. C. Young, A. J. Martinot, J. Buter, A. J. Minnaard, J. W. Annand, S. M. Fortune, B. B. Snider, I. Matsunaga, E. J. Rubin, T. Alber, D. B. Moody, Proc. Natl. Acad. Sci. USA 2014, 111, 2978-2983.
- (2014) Proc. Natl. Acad. Sci. USA , vol.111 , pp. 2978-2983
- Layre, E.¹ Lee, H.J.² Young, D.C.³ Martinot, A.J.⁴ Buter, J.⁵ Minnaard, A.J.⁶ Annand, J.W.⁷ Fortune, S.M.⁸ Snider, B.B.⁹ Matsunaga, I.¹⁰ Rubin, E.J.¹¹ Alber, T.¹² Moody, D.B.¹³

42
- 77955777534
- L. Prach, J. Kirby, J. D. Keasling, T. Alber, FEBS J. 2010, 277, 3588-3595.
- (2010) FEBS J. , vol.277 , pp. 3588-3595
- Prach, L.¹ Kirby, J.² Keasling, J.D.³ Alber, T.⁴

43
- 0000292269
- A. F. Barrero, J. F. Sanchez, E. J. Alvarez-Manzaneda, M. M. Dorado, A. Haidour, Phytochemistry 1993, 32, 1261-1265.
- (1993) Phytochemistry , vol.32 , pp. 1261-1265
- Barrero, A.F.¹ Sanchez, J.F.² Alvarez-Manzaneda, E.J.³ Dorado, M.M.⁴ Haidour, A.⁵

44
- 0343416305
- K. Bruns, Tetrahedron Lett. 1970, 11, 3263-3264.
- (1970) Tetrahedron Lett. , vol.11 , pp. 3263-3264
- Bruns, K.¹

45
- 0030028384
- F. Nagashima, H. Tanaka, Y. Asakawa, Phytochemistry 1996, 42, 93-96.
- (1996) Phytochemistry , vol.42 , pp. 93-96
- Nagashima, F.¹ Tanaka, H.² Asakawa, Y.³

46
- 0029163932
- A. Urzua, E. Tojo, J. Soto, Phytochemistry 1995, 38, 555-556.
- (1995) Phytochemistry , vol.38 , pp. 555-556
- Urzua, A.¹ Tojo, E.² Soto, J.³

47
- 0036236070
- M. Ono, T. Yanaka, M. Yamamoto, Y. Ito, T. Nohara, J. Nat. Prod. 2002, 65, 537-541.
- (2002) J. Nat. Prod. , vol.65 , pp. 537-541
- Ono, M.¹ Yanaka, T.² Yamamoto, M.³ Ito, Y.⁴ Nohara, T.⁵

48
- 0013575357
- D. V. Banthorpe, J. T. Brown, G. S. Morris, Phytochemistry 1990, 29, 2145-2148.
- (1990) Phytochemistry , vol.29 , pp. 2145-2148
- Banthorpe, D.V.¹ Brown, J.T.² Morris, G.S.³

49
- 0028467473
- A. Ulubelen, G. Topcu, C. Eri, U. Sönmez, M. Kartal, S. Kurucu, C. Bozok-Johansson, Phytochemistry 1994, 36, 971-974.
- (1994) Phytochemistry , vol.36 , pp. 971-974
- Ulubelen, A.¹ Topcu, G.² Eri, C.³ Sönmez, U.⁴ Kartal, M.⁵ Kurucu, S.⁶ Bozok-Johansson, C.⁷

50
- 70649115507
- C. Nakano, T. Hoshino, T. Sato, T. Toyomasu, T. Dairi, T. Sassa, Tetrahedron Lett. 2010, 51, 125-128.
- (2010) Tetrahedron Lett. , vol.51 , pp. 125-128
- Nakano, C.¹ Hoshino, T.² Sato, T.³ Toyomasu, T.⁴ Dairi, T.⁵ Sassa, T.⁶

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