Obafluorin
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| IUPAC name
2,3-dihydroxy-N-[(2R,3S)-2-[(4-nitrophenyl)methyl]-4-oxooxetan-3-yl]benzamide | |
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| Properties | |
| C17H14N2O7 | |
| Molar mass | 358.306 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Obafluorin is a β-lactone antibiotic with the molecular formula C17H14N2O7.[1][2] Obafluorin is produced by the bacterium Pseudomonas fluorescens.[3] Obafluorin is a inhibitor of serine hydroxymethyltransferase.[4]
References
[edit]- ↑ Scott, Thomas A.; Batey, Sibyl F.; Wiencek, Patrick; Chandra, Govind; Alt, Silke; Franklyn, Christopher S.; Wilkinson, Barrie (2019). "Immunity-Guided Identification of Threonyl-tRNA Synthetase as the Molecular Target of Obafluorin, a β-Lactone Antibiotic". ACS Chemical Biology. 14 (12): 2663–2671. bioRxiv 10.1101/704981. doi:10.1021/acschembio.9b00590. PMID 31675206.
- ↑ Tymiak, Adrienne A.; Culver, Catherine A.; Malley, Mary F.; Gougoutas, Jack Z. (December 1985). "Structure of obafluorin: an antibacterial β-lactone from Pseudomonas fluorescens". Journal of Organic Chemistry. 50 (26): 5491–5495. doi:10.1021/jo00350a010.
- ↑ Wells, J. Scott; Trejo, William H.; Principe, Pacifico A.; Sykes, Richard B. (1984). "Obafluorin, a novel β-lactone produced by Pseudomonas fluorescens. Taxonomy, fermentation and biological properties". Journal of Antibiotics. 37 (7): 802–803. doi:10.7164/antibiotics.37.802. PMID 6432765.
- ↑ Prasad, Neha (18 April 2015). "Obafluorin: A Potential Inhibitor of Serine Hydroxymethyl Trasferase [sic]". Undergraduate Research Symposium Posters.
Further reading
[edit]- "Next antibiotic may come from dirt bacteria". Futurity. 2 August 2019.
- Scott, Thomas A.; Heine, Daniel; Qin, Zhiwei; Wilkinson, Barrie (26 June 2017). "An L-threonine transaldolase is required for L-threo-β-hydroxy-α-amino acid assembly during obafluorin biosynthesis". Nature Communications. 8 (1) 15935. doi:10.1038/ncomms15935. ISSN 2041-1723. PMC 5490192. PMID 28649989.
- Herbert, Richard B.; Knaggs, Andrew R. (1992). "Biosynthesis of the antibiotic obafluorin from D-[U-13C]glucose and p-aminophenylalanine in Pseudomonas fluorescens". Journal of the Chemical Society, Perkin Transactions 1 (1): 103–107. doi:10.1039/P19920000103. ISSN 1364-5463.