Obafluorin

Base Information

• Chemical Name: Obafluorin
• CAS No.: 92121-68-1
• Molecular Formula: C17H14 N2 O7
• Molecular Weight: 358.3
• DSSTox Substance ID: DTXSID90238870
• Nikkaji Number: J374.918E
• Wikipedia: Obafluorin
• Wikidata: Q75068666
• Metabolomics Workbench ID: 116437
• Mol file: 92121-68-1.mol

Synonyms:obafluorin

Chemical Property of Obafluorin

Chemical Property:

• Vapor Pressure: 3.32E-17mmHg at 25°C
• Boiling Point: 644.4°Cat760mmHg
• Flash Point: 343.5°C
• PSA: 145.17000
• Density: 1.57g/cm³
• LogP: 2.37050
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 358.08010079
• Heavy Atom Count: 26
• Complexity: 556

Purity/Quality:

99% ^*data from raw suppliers

Obafluorin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1)O)O)C(=O)NC2C(OC2=O)CC3=CC=C(C=C3)[N+](=O)[O-]
• Isomeric 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-]
• Description: Obafluorin is a β-lactone antibiotic that has been found in P. fluorescens. It is active against S. aureus, S. faecalis, K. pneumoniae, and P. vulgaris (MIC = 125 μg/ml for all).

Technology Process of Obafluorin

There total 7 articles about Obafluorin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2,3-Dihydroxybenzoic acid (303-38-8) + (2S,3R)-2-amino-3-hydroxy-4-(4-nitrophenyl)butanoic acid (99268-38-9) → (+)-Obafluorin (92121-68-1) + (2S,3R)-2-<(2,3-Dihydroxybenzoyl)amino>-3-hydroxy-4-(4-nitrophenyl)butanoic acid (99268-39-0)

Guidance literature:

With potassium chloride; ATP; magnesium chloride; In aq. buffer; at 20 ℃; for 0.5h; Enzymatic reaction;

DOI:10.1038/nchembio.2374

Reference yield:

chlorure de 2,3-dioxosulfinylbenzoyle (70656-95-0) + (3S,4R)-3-Amino-4-<(4-nitrophenyl)methyl>-2-oxetanone 4-toluenesulfonate (137965-33-4) → (+)-Obafluorin (92121-68-1)

Guidance literature:

With pyridine; In dichloromethane; Yield given; 1.) -10 deg C, 30 min; -10 deg C to 20 deg C, 2 h, 2.) 20 deg C, 2 h;

DOI:10.1021/jo00092a025

Reference yield:

2-Oxo-2λ4-benzo[1,3,2]dioxathiole-4-carboxylic acid [(2R,3S)-2-(4-nitro-benzyl)-4-oxo-oxetan-3-yl]-amide → (+)-Obafluorin (92121-68-1)

Guidance literature:

With water;

DOI:10.1021/jo00027a006

upstream raw materials:

chlorure de 2,3-dioxosulfinylbenzoyle

(3S,4R)-3-Amino-4-<(4-nitrophenyl)methyl>-2-oxetanone 4-toluenesulfonate

2,3-Dihydroxybenzoic acid

(2S,3R)-2-amino-3-hydroxy-4-(4-nitrophenyl)butanoic acid

Downstream raw materials:

Acetic acid 2-acetoxy-6-{acetyl-[2-(4-nitro-benzyl)-4-oxo-oxetan-3-yl]-carbamoyl}-phenyl ester

2-(2,3-Dihydroxy-benzoylamino)-3-hydroxy-4-(4-nitro-phenyl)-butyric acid

(2S,3R)-2-<(2,3-Dihydroxybenzoyl)amino>-3-hydroxy-4-(4-nitrophenyl)butanoic acid