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Biosynthesis of fluorothreonine and fluoroacetic acid by the thienamycin producer, Streptomyces cattleya.
Open accessAbstract
An antimetabolite, THX, was isolated from fermentation broths of the thienamycin producer, Streptomyces cattleya, when the organism was grown in the presence of a fluorine-containing substrate. THX was subsequently identified as one of the four possible stereoisomers of 4-fluorothreonine. Inorganic fluoride or any one of a number of organofluorine compounds can be used as precursors of 4-fluorothreonine. In addition, 19F NMR has provided evidence that the organism synthesizes fluoroacetate under the same fermentation conditions. The in vitro antibacterial spectrum of 4-fluorothreonine is also presented.
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Citations
Cited by
Crystal structure and mechanism of a bacterial fluorinating enzyme
Dong, C., Huang, F., Deng, H., Schaffrath, C., Spencer, J. B., O'Hagan, D., & Naismith, J. H. (2004) · Nature · doi:10.1038/nature02280 · Cited by 335
Enzymatic fluorination and biotechnological developments of the fluorinase
O’Hagan, D., & Deng, H. (2015) · Chemical Reviews · doi:10.1021/cr500209t · Cited by 331
Fluorine-containing natural products
O’Hagan, D., & B. Harper, D. (1999) · Journal of Fluorine Chemistry · doi:10.1016/s0022-1139(99)00201-8 · Cited by 318
Murphy, C. D., Schaffrath, C., & O’Hagan, D. (2003) · Chemosphere · doi:10.1016/s0045-6535(03)00191-7 · Cited by 87
The Rare Fluorinated Natural Products and Biotechnological Prospects for Fluorine Enzymology
Chan, K. K. J., & O'Hagan, D. (2012) · Methods in Enzymology · doi:10.1016/b978-0-12-394291-3.00003-4 · Cited by 78
Metadata
- Authors
- SANADA, M., MIYANO, T., IWADARE, S., WILLIAMSON, J. M., ARISON, B. H., SMITH, J. L., DOUGLAS, A. W., LIESCH, J. M., & INAMINE, E.
- Venue
- The Journal of Antibiotics
- Published
- 1986
- Volume
- 39
- Issue
- 2
- Pages
- 259-265
- ISSN
- 0021-8820 (ISSN-L)
- 1881-1469
- OpenAlex
- W2327192134
- Cited by
- 166
- References
- 0
- FWCI
- 0.74
- Type
- journal article
- Language
- en
- Open access
- bronze
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- The paper
- SANADA, M., MIYANO, T., IWADARE, S., WILLIAMSON, J. M., ARISON, B. H., SMITH, J. L., DOUGLAS, A. W., LIESCH, J. M., & INAMINE, E. (1986). Biosynthesis of fluorothreonine and fluoroacetic acid by the thienamycin producer, Streptomyces cattleya. The Journal of Antibiotics. https://doi.org/10.7164/antibiotics.39.259
Data sources
Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
