Obafluorin | CAS# 92121-68-1 | B-lactone Antibiotic

MedKoo Cat#: 574085 | Name: Obafluorin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Obafluorin is a β-lactone antibiotic that has been found in P. fluorescens. Obafluorin is active against S. aureus, S. faecalis, K. pneumoniae, and P. vulgaris. Obafluorin is a novel covalent inhibitor of ThrRS.

Chemical Structure

Obafluorin

CAS#92121-68-1

Theoretical Analysis

MedKoo Cat#: 574085

Name: Obafluorin

CAS#: 92121-68-1

Chemical Formula: C17H14N2O7

Exact Mass: 358.0801

Molecular Weight: 358.31

Elemental Analysis: C, 56.99; H, 3.94; N, 7.82; O, 31.26

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 700.00
5mg	USD 1,900.00

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Synonym

Obafluorin

IUPAC/Chemical Name

2,3-dihydroxy-N-[(2R,3S)-2-[(4-nitrophenyl)methyl]-4-oxo-3-oxetanyl]-benzamide

InChi Key

AINNQKIVZOTQBB-KGLIPLIRSA-N

InChi Code

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

SMILES Code

O=C(C1=C(O)C(O)=CC=C1)N[C@H]2[C@@H](CC3=CC=C([N+]([O-])=O)C=C3)OC2=O

Appearance

A crystalline solid

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Obafluorin is a β-Lactone Antibiotic, that can be produced by Pseudomonas fluorescens ATCC 39502.

In vitro activity:

Obafluorin is active against both Gram-positive and -negative pathogens; however, the biological target was unknown. This study reports that obafluorin targets threonyl-tRNA synthetase, and we identify a homologue, ObaO, which confers immunity to the obafluorin producer. Disruption of obaO in P. fluorescens ATCC 39502 results in obafluorin sensitivity, whereas expression in sensitive E. coli strains confers resistance. Reference: ACS Chem Biol. 2019 Dec 20;14(12):2663-2671. https://pubmed.ncbi.nlm.nih.gov/31675206/

In vivo activity:

TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 358.31 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

Scott TA, Batey SFD, Wiencek P, Chandra G, Alt S, Francklyn CS, Wilkinson B. Immunity-Guided Identification of Threonyl-tRNA Synthetase as the Molecular Target of Obafluorin, a β-Lactone Antibiotic. ACS Chem Biol. 2019 Dec 20;14(12):2663-2671. doi: 10.1021/acschembio.9b00590. Epub 2019 Nov 14. PMID: 31675206.

In vitro protocol:

In vivo protocol:

TBD

1: Qiao H, Wang Z, Yang H, Xia M, Yang G, Bai F, Wang J, Fang P. Specific glycine-dependent enzyme motion determines the potency of conformation selective inhibitors of threonyl-tRNA synthetase. Commun Biol. 2024 Jul 16;7(1):867. doi: 10.1038/s42003-024-06559-x. PMID: 39014102; PMCID: PMC11252418. 2: Patel KD, Oliver RA, Lichstrahl MS, Li R, Townsend CA, Gulick AM. The structure of the monobactam-producing thioesterase domain of SulM forms a unique complex with the upstream carrier protein domain. J Biol Chem. 2024 Jun 20;300(8):107489. doi: 10.1016/j.jbc.2024.107489. Epub ahead of print. PMID: 38908753; PMCID: PMC11298585. 3: Patel KD, Oliver RA, Lichstrahl MS, Li R, Townsend CA, Gulick AM. The structure of the monobactam-producing thioesterase domain of SulM forms a unique complex with the upstream carrier protein domain. bioRxiv [Preprint]. 2024 Apr 6:2024.04.06.588331. doi: 10.1101/2024.04.06.588331. Update in: J Biol Chem. 2024 Jun 20;300(8):107489. doi: 10.1016/j.jbc.2024.107489. PMID: 38617275; PMCID: PMC11014566. 4: Batey SFD, Davie MJ, Hems ES, Liston JD, Scott TA, Alt S, Francklyn CS, Wilkinson B. The catechol moiety of obafluorin is essential for antibacterial activity. RSC Chem Biol. 2023 Aug 21;4(11):926-941. doi: 10.1039/d3cb00127j. PMID: 37920400; PMCID: PMC10619133. 5: Qiao H, Xia M, Cheng Y, Zhou J, Zheng L, Li W, Wang J, Fang P. Tyrosine- targeted covalent inhibition of a tRNA synthetase aided by zinc ion. Commun Biol. 2023 Jan 27;6(1):107. doi: 10.1038/s42003-023-04517-7. PMID: 36707692; PMCID: PMC9880928. 6: Kumar P, Meza A, Ellis JM, Carlson GA, Bingman CA, Buller AR. l-Threonine Transaldolase Activity Is Enabled by a Persistent Catalytic Intermediate. ACS Chem Biol. 2021 Jan 15;16(1):86-95. doi: 10.1021/acschembio.0c00753. Epub 2020 Dec 18. PMID: 33337128; PMCID: PMC8331687. 7: Scott TA, Batey SFD, Wiencek P, Chandra G, Alt S, Francklyn CS, Wilkinson B. Immunity-Guided Identification of Threonyl-tRNA Synthetase as the Molecular Target of Obafluorin, a β-Lactone Antibiotic. ACS Chem Biol. 2019 Dec 20;14(12):2663-2671. doi: 10.1021/acschembio.9b00590. Epub 2019 Nov 14. PMID: 31675206. 8: Kreitler DF, Gemmell EM, Schaffer JE, Wencewicz TA, Gulick AM. The structural basis of N-acyl-α-amino-β-lactone formation catalyzed by a nonribosomal peptide synthetase. Nat Commun. 2019 Jul 31;10(1):3432. doi: 10.1038/s41467-019-11383-7. PMID: 31366889; PMCID: PMC6668435. 9: Scott TA, Heine D, Qin Z, Wilkinson B. An L-threonine transaldolase is required for L-threo-β-hydroxy-α-amino acid assembly during obafluorin biosynthesis. Nat Commun. 2017 Jun 26;8:15935. doi: 10.1038/ncomms15935. PMID: 28649989; PMCID: PMC5490192. 10: Schaffer JE, Reck MR, Prasad NK, Wencewicz TA. β-Lactone formation during product release from a nonribosomal peptide synthetase. Nat Chem Biol. 2017 Jul;13(7):737-744. doi: 10.1038/nchembio.2374. Epub 2017 May 15. PMID: 28504677. 11: Wells JS, Trejo WH, Principe PA, Sykes RB. Obafluorin, a novel beta-lactone produced by Pseudomonas fluorescens. Taxonomy, fermentation and biological properties. J Antibiot (Tokyo). 1984 Jul;37(7):802-3. doi: 10.7164/antibiotics.37.802. PMID: 6432765.