140694-66-2

Upstream product

• 119-62-0 (1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol 
• 56-75-7 chloramphenicol 
• 555-16-8 4-nitrobenzaldehdye 
• 50961-69-8 (1RS,2RS)-2-acetylamino-1-(4-dimethylamino-phenyl)-propane-1,3-diol 
• 861057-07-0 N-[2-(4-dimethylamino-phenyl)-1-hydroxymethyl-2-oxo-ethyl]-acetamide 

Downstream Products

• 57704-36-6 (1R,2R)-1-(4-amino-phenyl)-2-(2,2-dichloro-acetylamino)-propane-1,3-diol; hydrochloride 
• 165063-94-5 2,2-Dichloro-N-{(1R,2R)-2-[4-(2,2-dichloro-acetylamino)-phenyl]-2-hydroxy-1-hydroxymethyl-ethyl}-acetamide 
• 7411-64-5 N-((1R,2R)-1-(4-aminophenyl)-1,3-dihydroxypropan-2-yl)-2,2-dichloroacetamide 
• 56-75-7 chloramphenicol 
• 13838-08-9 Azidamfenicol 

Relevant academic research and scientific papers

CmlI is an N-oxygenase in the biosynthesis of chloramphenicol

The N-oxygenation of an amine group is one of the steps in the biosynthesis of the antibiotic chloramphenicol. The non-heme di-iron enzyme CmlI was identified as the enzyme catalyzing this reaction through bioinformatics studies and reconstitution of enzymatic activity. In vitro reconstitution was achieved using phenazine methosulfate and NADH as electron mediators, while in vivo activity was demonstrated in Escherichia coli using two substrates. Kinetic analysis showed a biphasic behavior of the enzyme. Oxidized hydroxylamine and nitroso compounds in the reaction were detected both in vitro and in vivo based on LC-MS. The active site metal was confirmed to be iron based on a ferrozine assay. These findings provide new insights into the biosynthesis of chloramphenicol and could lead to further development of CmlI as a useful biocatalyst.

Catalytic Syn-Selective Nitroaldol Approach to Amphenicol Antibiotics: Evolution of a Unified Asymmetric Synthesis of (-)-Chloramphenicol, (-)-Azidamphenicol, (+)-Thiamphenicol, and (+)-Florfenicol

A unified strategy for an efficient and high diastereo- and enantioselective synthesis of (-)-chloramphenicol, (-)-azidamphenicol, (+)-thiamphenicol, and (+)-florfenicol based on a key catalytic syn-selective Henry reaction is reported. The stereochemistry of the ligand-enabled copper(II)-catalyzed aryl aldehyde Henry reaction of nitroethanol was first explored to forge a challenging syn-2-amino-1,3-diol structure unit with vicinal stereocenters with excellent stereocontrol. Multistep continuous flow manipulations were carried out to achieve the efficient asymmetric synthesis of this family of amphenicol antibiotics.

Correlation between antigen-combining-site structures and functions within a panel of catalytic antibodies generated against a single transition state analog

The diversity of the immune response, which can provide a panel of catalytic antibodies with varying degrees of catalytic activity and substrate specificity by immunization with a single hapten, raises the question concerning the extent to which a rationa