Obafluorin

Obafluorin
Names
	IUPAC name 2,3-dihydroxy-N-[(2R,3S)-2-[(4-nitrophenyl)methyl]-4-oxooxetan-3-yl]benzamide
Identifiers
CAS Number	92121-68-1 ;
3D model (JSmol)	Interactive image;
PubChem CID	146354;
CompTox Dashboard (EPA)	90238870;
	InChI InChI=1S/C17H14N2O7/c20-12-3-1-2-11(15(12)21)16(22)18-14-13(26-17(14)23)8-9-4-6-10(7-5-9)19(24)25/h1-7,13-14,20-21H,8H2,(H,18,22)/t13-,14+/m1/s1 Key: AINNQKIVZOTQBB-KGLIPLIRSA-N;
	SMILES C1=CC(=C(C(=C1)O)O)C(=O)N[C@H]2[C@H](OC2=O)CC3=CC=C(C=C3)[N+](=O)[O-];
Properties
Chemical formula	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). Infobox references

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

^ Scott, Thomas A.; Batey, Sibyl F.; Wiencek, Patrick; Chandra, Govind; Alt, Silke; Franklyn, Christopher S.; Wilkinson, Barrie (17 July 2019). "Self-immunity guided identification of threonyl-tRNA synthetase as the molecular target of obafluorin, a β-lactone antibiotic". bioRxiv. doi:10.1101/704981. S2CID 201196822.
^ 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.

"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.

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