4423-58-9

Basic information

• Product Name: DL-THREO-2-ACETAMIDO-L-(4-NITROPHENYL)-L,3-PROPANEDIOL
• Synonyms: DL-THREO-2-ACETAMIDO-L-(4-NITROPHENYL)-L,3-PROPANEDIOL;DechlorochloraMphenicol, DidechloraMphenicol
• CAS NO: 4423-58-9
• Molecular Formula: C₁₁H₁₄N₂O₅
• Molecular Weight: 254.23926
• Mol File: 4423-58-9.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: DL-THREO-2-ACETAMIDO-L-(4-NITROPHENYL)-L,3-PROPANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: DL-THREO-2-ACETAMIDO-L-(4-NITROPHENYL)-L,3-PROPANEDIOL(4423-58-9)
• EPA Substance Registry System: DL-THREO-2-ACETAMIDO-L-(4-NITROPHENYL)-L,3-PROPANEDIOL(4423-58-9)

Safety Data

• Hazardous Substances Data: 4423-58-9(Hazardous Substances Data)

Usage

Description

Corynecin I is a chloramphenicol-like antibiotic originally isolated from Corynebacterium. It is active against Gram-positive and Gram-negative bacteria with MIC values of 5.2-83 μg/ml for S. sonnei, P. vulgaris, K. pneumoniae, and S. aureus among others.

Uses

Corynecin I is a member of a naturally-occurring complex of chloramphenicol-like acyl nitrophenylpropylamines isolated from Corynebacterium hydrocarboclastus in 1972. Corynecin I is active against Gram positive and Gram negative bacteria. Although less potent than chloramphenicol, corynecin I shows a similar species selectivity.

Upstream product

• 3144-16-9 (1S)-10-camphorsulfonic acid 
• 1885-08-1 (1RS,2RS)-2-acetylamino-1-(4-nitro-phenyl)-propane-1,3-diol 
• 51259-82-6 (1R,2R)-1,3-diacetoxy-2-acetylamino-1-(4-nitro-phenyl)-propane 
• 119-62-0 (1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 141-78-6 ethyl acetate 
• 3123-13-5 (R)-(+)-α-Acetamino-β-hydroxy-p-nitro-propiophenon 
• 119-62-0 (+/-)-threo-1-(4-nitro-phenyl)-2-amino-1,3-propanediol 
• 56-75-7 chloramphenicol 
• 18735-12-1 (R)-(+)-α-Acetamino-β-acetoxy-p-nitro-propiophenon 
• 3123-13-5 N-[1-hydroxymethyl-2-(4-nitro-phenyl)-2-oxo-ethyl]-acetamide 
• 33485-02-8 (1RS,2RS)-1,3-diacetoxy-2-acetylamino-1-(4-nitro-phenyl)-propane 
• 88407-25-4 (2RS,3RS)-3-acetoxy-2-amino-3-(4-nitro-phenyl)-propan-1-ol; hydrochloride 

Downstream Products

• 19934-66-8 threo-(1S,2S)-2-acetamino-1-(4-nitrophenyl)-1,3-propanediol 
• 119-62-0 (1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol 
• 50961-69-8 (1R,2R)-2-acetylamino-1-(4-dimethylamino-phenyl)-propane-1,3-diol 
• 35742-52-0 N-[(1RS,2RS)-2-(4-amino-phenyl)-2-hydroxy-1-hydroxymethyl-ethyl]-acetamide 
• 119-62-0 (+/-)-threo-1-(4-nitro-phenyl)-2-amino-1,3-propanediol 
• 50961-69-8 (1RS,2RS)-2-acetylamino-1-(4-dimethylamino-phenyl)-propane-1,3-diol 
• 110461-00-2 N-[4t-(4-nitro-phenyl)-2ξ-oxo-2λ⁴-[1,3,2]dioxathian-5r-yl]-acetamide 
• 110461-00-2 N-[4c-(4-nitro-phenyl)-2ξ-oxo-2λ⁴-[1,3,2]dioxathian-5r-yl]-acetamide 
• 88407-25-4 (2RS,3RS)-3-acetoxy-2-amino-3-(4-nitro-phenyl)-propan-1-ol; hydrochloride 
• 1885-08-1 (1RS,2RS)-2-acetylamino-1-(4-nitro-phenyl)-propane-1,3-diol 
• 52183-38-7 (+/-)-[2-methyl-5t-(4-nitro-phenyl)-4,5-dihydro-oxazol-4r-yl]-methanol 
• 71115-69-0 erythro-2-amino-1-(p-nitrophenyl)-1,3-propanediol 
• 2792-51-0 (1R,2S)-(+)-2-amino-1-(4-nitrophenyl)-1,3-propanediol 
• 15935-03-2 4-((1RS.2RS)-2-acetylamino-1,3-dihydroxy-propyl)-benzonitrile 

Relevant articles and documents

An Acyl Transfer Reaction Catalyzed by an Epimerase MarH

MarH, a small protein (129 amino acids) belonging to the cupin superfamily, was previously characterized as an epimerase involved in the (2S,3S)-β-methyltryptophan formation in the maremycin biosynthesis. Here, MarH was discovered to act as an acyltransferase that can catalyze the 3-O-acylation of chloramphenicol. Furthermore, MarH can catalyze N-acylation of deacylated chloramphenicol analogue thereby activating them for 3-O-acylation. By systematic site-directed mutagenesis, H64 was revealed as a potential catalytic base that deprotonates the acyl acceptor substrate. Nucleophilic attack at the carbonyl carbon of the acyl donor then gives the acylation product.

ANTIMICROBIAL AGENTS

The present invention relates to the field of anti-infective, anti-proliferative, anti-inflammatory, and prokinetic agents. More particularly, the invention relates to substituted aromatic compounds useful as therapeutic agents.

Reversed-phase liquid chromatographic separation of enantiomeric and diastereomeric bases related to chloramphenicol and thiamphenicol.

The important antimicrobial agents chloramphenicol and thiamphenicol are N-acylated amines whose chemical structures include two chiral centers. Each drug is the single enantiomer of R,R configuration. The N-deacylated bases of the drugs are important intermediates in their synthesis and optical resolution. In this report, reversed-phase HPLC methods are described for the separation of enantiomeric and diastereomeric bases of the two drugs and of two closely related bases used in some syntheses of the drugs. The stereoisomeric bases were derivatized with a homochiral isothiocyanate and the resulting diastereomeric thioureas were separated on C18 columns with methanol:water mixtures as mobile phases and detection at 254 nm. The four stereoisomeric bases of chloramphenicol and those of its unnitrated analogue were thus separable after derivatization with 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate. This reagent also allowed the separation of the D-threo isomer of the p-mercaptomethyl analogue of thiamphenicol base from its stereoisomers. The stereoisomers of thiamphenicol base were similarly separated with (R)-alpha-methylbenzyl isothiocyanate as the derivatizing agent. The diastereomers of chloramphenicol base and of thiamphenicol base were chromatographically separable after derivatization with the nonchiral reagent benzyl isothiocyanate. The procedures developed may be useful in the determination of the stereoisomeric composition of the drugs in research and in quality control, and may be applicable to other similar agents whose chemistry and pharmacology are receiving considerable attention.