SCOPUS 정보 검색 플랫폼

Angewandte Chemie - International Edition

Volumn 48, Issue 34, 2009, Pages 6257-6261

An environmental DNA-derived type II polyketide biosynthetic pathway encodes the biosynthesis of the pentacyclic polyketide erdacin

(3) King, Ryan W a Bauer, John D a Brady, Sean F a

a ROCKEFELLER UNIVERSITY (United States)

Author keywords

Biosynthesis; DNA; Metagenomics; Natural products; Polyketides

Indexed keywords

BIOSYNTHETIC PATHWAY; DESERT SOILS; METAGENOMICS; NATURAL PRODUCTS; POLYKETIDE SYNTHASE GENES; POLYKETIDES; TYPE II;

BIOCHEMISTRY; BIOSYNTHESIS; CLONING; DNA; NUCLEIC ACIDS;

GENES;

DNA; ERDACIN; MACROLIDE; POLYCYCLIC HYDROCARBON; POLYKETIDE SYNTHASE;

ARTICLE; CHEMISTRY; GENETICS; ISOLATION AND PURIFICATION; METABOLISM; MICROBIOLOGY; MULTIGENE FAMILY;

DNA; MACROLIDES; MULTIGENE FAMILY; POLYCYCLIC COMPOUNDS; POLYKETIDE SYNTHASES; SOIL MICROBIOLOGY;

EID: 70349923903 PISSN: 14337851 EISSN: None Source Type: Journal
DOI: 10.1002/anie.200901209 Document Type: Article

Times cited : (42)

References (31)

1
- 0242523909
- M. S. Rappe, S. J. Giovannoni, Annu. Rev. Microbiol. 2003, 57, 369.
- (2003) Annu. Rev. Microbiol , vol.57 , pp. 369
- Rappe, M.S.¹ Giovannoni, S.J.²

2
- 0037052493
- V. Torsvik, L. Ovreas, T. F. Thingstad, Science 2002, 296, 1064.
- (2002) Science , vol.296 , pp. 1064
- Torsvik, V.¹ Ovreas, L.² Thingstad, T.F.³

3
- 0036677450
- T. P. Curtis, W. T. Sloan, J. W. Scanneil, Proc. Natl. Acad. Sci. USA 2002, 99, 10494.
- (2002) Proc. Natl. Acad. Sci. USA , vol.99 , pp. 10494
- Curtis, T.P.¹ Sloan, W.T.² Scanneil, J.W.³

4
- 0025256110
- V. Torsvik, K. Saite, R. Sorheim, J. Goksoyr, Appl. Environ. Microbiol. 1990, 56, 776.
- (1990) Appl. Environ. Microbiol , vol.56 , pp. 776
- Torsvik, V.¹ Saite, K.² Sorheim, R.³ Goksoyr, J.⁴

5
- 9244230571
- J. Piel, D. Hui, G. Wen, D. Butzke, M. Platzer, N. Fusetani, S. Matsunaga, Proc. Natl. Acad. Sci. USA 2004, 101, 16222.
- (2004) Proc. Natl. Acad. Sci. USA , vol.101 , pp. 16222
- Piel, J.¹ Hui, D.² Wen, G.³ Butzke, D.⁴ Platzer, M.⁵ Fusetani, N.⁶ Matsunaga, S.⁷

6
- 23744472955
- A. Schirmer, R. Gadkari, C. D. Reeves, F. Ibrahim, E. F DeLong, C. R. Hutchinson, Appl. Environ. Microbiol. 2005, 71, 4840.
- (2005) Appl. Environ. Microbiol , vol.71 , pp. 4840
- Schirmer, A.¹ Gadkari, R.² Reeves, C.D.³ Ibrahim, F.⁴ DeLong, E.F.⁵ Hutchinson, C.R.⁶

7
- 0346035740
- S. Courtois, C. M. Cappellano, M. Ball, F. X. Francou, P. Normand, G. Helynck, A. Martinez, S. J. Kolvek, J. Hopke, M. S. Osburne, P. R. August, R. Nalin, M. Guerineau, P. Jeannin, P. Simonet, J. L. Pernodet, Appl. Environ. Microbiol. 2003, 69, 49.
- (2003) Appl. Environ. Microbiol , vol.69 , pp. 49
- Courtois, S.¹ Cappellano, C.M.² Ball, M.³ Francou, F.X.⁴ Normand, P.⁵ Helynck, G.⁶ Martinez, A.⁷ Kolvek, S.J.⁸ Hopke, J.⁹ Osburne, M.S.¹⁰ August, P.R.¹¹ Nalin, R.¹² Guerineau, M.¹³ Jeannin, P.¹⁴ Simonet, P.¹⁵ Pernodet, J.L.¹⁶

8
- 35048880555
- S. F Brady, J. D. Bauer, M. F Clarke-Pearson, R. Daniels, J. Am. Chem. Soc. 2007, 129, 12102.
- (2007) J. Am. Chem. Soc , vol.129 , pp. 12102
- Brady, S.F.¹ Bauer, J.D.² Clarke-Pearson, M.F.³ Daniels, R.⁴

9
- 0030690924
- K. T. Seow, G. Meurer, M. Gerlitz, E. Wendt-Pienkowski, C. R. Hutchinson, J. Davies, J. Bacteriol. 1997, 179, 7360.
- (1997) J. Bacteriol , vol.179 , pp. 7360
- Seow, K.T.¹ Meurer, G.² Gerlitz, M.³ Wendt-Pienkowski, E.⁴ Hutchinson, C.R.⁵ Davies, J.⁶

10
- 4644371642
- A. Ginolhac, C. Jarrin, B. Gillet, P. Robe, P. Pujic, K. Tuphile, H. Bertrand, T. M. Vogel, G. Perriere, P. Simonet, R. Nalin, Appl. Environ. Microbiol. 2004, 70, 5522.
- (2004) Appl. Environ. Microbiol , vol.70 , pp. 5522
- Ginolhac, A.¹ Jarrin, C.² Gillet, B.³ Robe, P.⁴ Pujic, P.⁵ Tuphile, K.⁶ Bertrand, H.⁷ Vogel, T.M.⁸ Perriere, G.⁹ Simonet, P.¹⁰ Nalin, R.¹¹

11
- 33846923183
- C. Hertweck, A. Luzhetskyy, Y. Rebets, A. Bechthold, Nat. Prod. Rep. 2007, 24, 162.
- (2007) Nat. Prod. Rep , vol.24 , pp. 162
- Hertweck, C.¹ Luzhetskyy, A.² Rebets, Y.³ Bechthold, A.⁴

12
- 0000427346
- B. Shen, Curr. Top. Chem. 2000, 209, 1.
- (2000) Curr. Top. Chem , vol.209 , pp. 1
- Shen, B.¹

13
- 0029064652
- R. McDaniel, S. Ebert-Khosla, D. A. Hopwood, C. Khosla, Nature 1995, 375, 549.
- (1995) Nature , vol.375 , pp. 549
- McDaniel, R.¹ Ebert-Khosla, S.² Hopwood, D.A.³ Khosla, C.⁴

14
- 0028575694
- R. McDaniel, S. Ebert-Khosla, D. A. Hopwood, C. Khosla, J. Am. Chem. Soc. 1994, 116, 10855.
- (1994) J. Am. Chem. Soc , vol.116 , pp. 10855
- McDaniel, R.¹ Ebert-Khosla, S.² Hopwood, D.A.³ Khosla, C.⁴

15
- 0032401977
- A. L. Matharu, R. J. Cox, J. Crosby, K. J. Byrom, T. J. Simpson, Chem. Biol. 1998, 5, 699.
- (1998) Chem. Biol , vol.5 , pp. 699
- Matharu, A.L.¹ Cox, R.J.² Crosby, J.³ Byrom, K.J.⁴ Simpson, T.J.⁵

16
- 18444368437
- B. Wawrik, L. Kerkhof, G. J. Zylstra, J. J. Kukor, Appl. Environ. Microbiol. 2005, 71, 2232.
- (2005) Appl. Environ. Microbiol , vol.71 , pp. 2232
- Wawrik, B.¹ Kerkhof, L.² Zylstra, G.J.³ Kukor, J.J.⁴

17
- 67651015405
- M. Pang, G. A. Tan, N. Abdullah, C. Lee, C. Ng, Biotechnology 2008, 7, 660.
- (2008) Biotechnology , vol.7 , pp. 660
- Pang, M.¹ Tan, G.A.² Abdullah, N.³ Lee, C.⁴ Ng, C.⁵

18
- 34248151342
- B. Wawrik, D. Kutliev, U. A. Abdivasievna, J. J. Kukor, G. J. Zylstra, L. Kerkhof, Appl. Environ. Microbiol. 2007, 73, 2982.
- (2007) Appl. Environ. Microbiol , vol.73 , pp. 2982
- Wawrik, B.¹ Kutliev, D.² Abdivasievna, U.A.³ Kukor, J.J.⁴ Zylstra, G.J.⁵ Kerkhof, L.⁶

19
- 34250220631
- S. F. Brady, Nat. Protoc. 2007, 2, 1297.
- (2007) Nat. Protoc , vol.2 , pp. 1297
- Brady, S.F.¹

20
- 56249128990
- J. J. Banik, S. F. Brady, Proc. Natl. Acad. Sci. USA 2008, 105, 17273.
- (2008) Proc. Natl. Acad. Sci. USA , vol.105 , pp. 17273
- Banik, J.J.¹ Brady, S.F.²

21
- 70349964303
- -1). Erdacin (1) eluted at 14.9 min. The trivial name erdacin is derived from erda, the old english word for earth or soil.
- -1). Erdacin (1) eluted at 14.9 min. The trivial name erdacin is derived from "erda", the old english word for earth or soil.

22
- 70349943695
- Erdacin (1, 1HNMR (600 MHz, CD3OD with 0.1% trifluoro-acetic acid, δ, 7.40 (m, 2H; H-17,18, 7.28 (t, J, 7.7Hz, 1H; H-8, 7.16 (d, J=7.1 Hz, 1H; H-7, 6.92 (d, J=7.7 Hz, 1 H; H-9, 6.73 (d, J, 7.7 Hz, 1H; H-19, 4.29 (s, 1H; H-13, 2.53 (s, 3H; H-23, 1.72 ppm (s, 3H; H-26, 13CNMR (150 MHz, CD3OD with 0.1% trifluoroacetic acid, δ, 205.5 (C-22, 203.5 (C-25, 188.4 (C-1, 176.6 (C24, 165.3 (C-20, 156.7 (C-10, 153.7 (C-2, 143.3 (C-5, 138.8 (C-18, 135.6 (C-16, 134.6 (C-14, 133.4 (C-6, 131.3 (C-8, 131.2 (C-4, 130.6 (C-15, 127.7 (C-3, 123.8 (C-11, 120.6 (C-7, 119.1 (C-17, 118.7 (C-9, 118.4 (C-19, 114.1 (C-21, 75.5 (C-12, 64.6 (C-13, 30.3 (C-23, 27.9 ppm C-26, HRESI-MS: m/z 475.1037, calcd for C,6H 19O9, 475.1029. 1H and 13C spectra for erdacin are included in the Supporting Information. CDCC 721152 contains the sup
- 13C spectra for erdacin are included in the Supporting Information. CDCC 721152 contains the supplementary crystallography data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data request/cif.

23
- 15944375464
- H. Lessmann, R. P. Maskey, S. Fotso, H. Lackner, H. Laatsch, Z. Naturforsch. B 2005, 60, 189.
- (2005) Z. Naturforsch. B , vol.60 , pp. 189
- Lessmann, H.¹ Maskey, R.P.² Fotso, S.³ Lackner, H.⁴ Laatsch, H.⁵

24
- 84945041210
- H. Lessmann, J. Krupa, H. Lackner, P. G. Jones, Naturforsch. B 1989, 44, 353.
- (1989) Naturforsch. B , vol.44 , pp. 353
- Lessmann, H.¹ Krupa, J.² Lackner, H.³ Jones, P.G.⁴

25
- 0027146033
- A. Yenesew, J. A. Ogur, H. Duddeck, Phytochemistry 1993, 34, 1442.
- (1993) Phytochemistry , vol.34 , pp. 1442
- Yenesew, A.¹ Ogur, J.A.² Duddeck, H.³

26
- 0141961793
- M. Ozawa, T. Taguchi, T. Itoh, Y. Ebuizuka, K. I. Booker-Milburn, G. R. Stephenson, K. Ichinose, Tetrahedron 2003, 59, 8793.
- (2003) Tetrahedron , vol.59 , pp. 8793
- Ozawa, M.¹ Taguchi, T.² Itoh, T.³ Ebuizuka, Y.⁴ Booker-Milburn, K.I.⁵ Stephenson, G.R.⁶ Ichinose, K.⁷

27
- 0141734633
- P. Brünker, K. McKinney, O. Sterner, W. Minas, J. E. Bailey, Gene 1999, 227, 125.
- (1999) Gene , vol.227 , pp. 125
- Brünker, P.¹ McKinney, K.² Sterner, O.³ Minas, W.⁴ Bailey, J.E.⁵

28
- 0032213555
- K. Ichinose, D. J. Bedford, D. Tornus, A. Bechthold, M. J. Bibb, W. P. Revill, H. G. Floss, D. A. Hopwood, Chem. Biol. 1998, 5, 647.
- (1998) Chem. Biol , vol.5 , pp. 647
- Ichinose, K.¹ Bedford, D.J.² Tornus, D.³ Bechthold, A.⁴ Bibb, M.J.⁵ Revill, W.P.⁶ Floss, H.G.⁷ Hopwood, D.A.⁸

29
- 0038148677
- K. Ichinose, M. Ozawa, K. Itou, K. Kunieda, Y. Ebizuka, Microbiology 2003, 149, 1633.
- (2003) Microbiology , vol.149 , pp. 1633
- Ichinose, K.¹ Ozawa, M.² Itou, K.³ Kunieda, K.⁴ Ebizuka, Y.⁵

30
- 31344443334
- S. P. Wilkinson, A. Grove, Curr. Issues Mol. Biol. 2006, 8, 51.
- (2006) Curr. Issues Mol. Biol , vol.8 , pp. 51
- Wilkinson, S.P.¹ Grove, A.²

31
- 20844445334
- R. L. Prior, X. Wu, K. Schaich, J. Agric. Food Chem. 2005, 53, 4290.
- (2005) J. Agric. Food Chem , vol.53 , pp. 4290
- Prior, R.L.¹ Wu, X.² Schaich, K.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.