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A butenolide intermediate in methylenomycin furan biosynthesis is implied by incorporation of stereospecifically C-13-labelled glycerols
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Corre, Christophe, Haynes, Stuart W., Malet, Nicolas, Song, Lijiang and Challis, Gregory L.. (2011) A butenolide intermediate in methylenomycin furan biosynthesis is implied by incorporation of stereospecifically C-13-labelled glycerols. Chemical Communications, Vol.46 (No.23). pp. 4079-4081. ISSN 1359-7345
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Official URL: http://dx.doi.org/10.1039/c000496k
Abstract
The label from [3-C-13]-L-glycerol is incorporated into the hydroxymethyl group of methylenomycin furans suggesting a butenolide intermediate in their biosynthesis.
| Item Type: | Journal Article |
|---|---|
| Subjects: | Q Science > QD Chemistry Q Science > QR Microbiology |
| Divisions: | Faculty of Science > Chemistry |
| Library of Congress Subject Headings (LCSH): | Streptomyces coelicolor, Antibiotic-producing organisms, Streptomycin, Biosynthesis, Furans |
| Journal or Publication Title: | Chemical Communications |
| Publisher: | Royal Society of Chemistry |
| ISSN: | 1359-7345 |
| Date: | 2011 |
| Volume: | Vol.46 |
| Number: | No.23 |
| Number of Pages: | 3 |
| Page Range: | pp. 4079-4081 |
| Identification Number: | 10.1039/c000496k |
| Status: | Peer Reviewed |
| Publication Status: | Published |
| Access rights to Published version: | Restricted or Subscription Access |
| Funder: | Biotechnology and Biological Sciences Research Council (Great Britain) (BBSRC) |
| Grant number: | BB/E008003/1 (BBSRC) |
| References: | 1 M. J. Bibb, Curr. Opin. Microbiol., 2005, 8, 208–215. 2 A. S. Khokhlov, I. I. Tovarova, L. N. Borisova, S. A. Pliner, L. N. Shevchenko, E. I. Kornitskaia, N. S. Ivkina and I. A. Rapoport, Dokl. Akad. Nauk SSSR, 1967, 1777, 232–237. 3 K. Pawlik, M. Kotowska, K. F. Chater, K. Kuczek and E. Takano, Arch. Microbiol., 2007, 187, 87–99. 4 S. Sakuda, A. Higashi, T. Nihira and Y. Yamada, J. Am. Chem. Soc., 1990, 112, 898–899. 5 C. Corre, L. Song, S. O’Rourke, K. F. Chater and G. L. Challis, Proc. Natl. Acad. Sci. U. S. A., 2008, 105, 17510–17515. 6 S. Grond, H. J. Langer, P. Henne, I. Sattler, R. Thiericke, S. Grabley, H. Za¨ hner and A. Zeeck, Eur. J. Org. Chem., 2000, 929–937. 7 J. Kato, N. Funa, H. Watanabe, Y. Onishi and S. Horinouchi, Proc. Natl. Acad. Sci. U. S. A., 2007, 104, 2378–2383. 8 J. B. Davis, J. D. Bailey and J. K. Sello, Org. Lett., 2009, 11, 2984–2987. 9 Intramolecular proton transfer to the acetylene in 4 would generate an alternative allene intermediate, which could also undergo loss of formaldehyde to yield an enolate. |
| URI: | http://wrap.warwick.ac.uk/id/eprint/5788 |
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