10318-17-9Relevant academic research and scientific papers
Monitoring bacterial resistance to chloramphenicol and other antibiotics by liquid chromatography electrospray ionization tandem mass spectrometry using selected reaction monitoring
Haag, Anthony M.,Medina, Audrie M.,Royall, Ariel E.,Herzog, Norbert K.,Niesel, David W.
, p. 732 - 739 (2013/07/27)
Antibiotic resistance is a growing problem worldwide. For this reason, clinical laboratories often determine the susceptibility of the bacterial isolate to a number of different antibiotics in order to establish the most effective antibiotic for treatment. Unfortunately, current susceptibility assays are time consuming. Antibiotic resistance often involves the chemical modification of an antibiotic to an inactive form by an enzyme expressed by the bacterium. Selected reaction monitoring (SRM) has the ability to quickly monitor and identify these chemical changes in an unprecedented time scale. In this work, we used SRM as a technique to determine the susceptibility of several different antibiotics to the chemically modifying enzymes β-lactamase and chloramphenicol acetyltransferase, enzymes used by bacteria to confer resistance to major classes of commonly used antibiotics. We also used this technique to directly monitor the effects of resistant bacteria grown in a broth containing a specific antibiotic. Because SRM is highly selective and can also identify chemical changes in a multitude of antibiotics in a single assay, SRM has the ability to detect organisms that are resistant to multiple antibiotics in a single assay. For these reasons, the use of SRM greatly reduces the time it takes to determine the susceptibility or resistance of an organism to a multitude of antibiotics by eliminating the time-consuming process found in other currently used methods. Copyright 2013 John Wiley & Sons, Ltd. Copyright
Enzymatic regioselective production of chloramphenicol esters
Bizerra, Ayla M.C.,Montenegro, Tasso G.C.,Lemos, Telma L.G.,De Oliveira, Maria C.F.,De Mattos, Marcos C.,Lavandera, Iván,Gotor-Fernández, Vicente,De Gonzalo, Gonzalo,Gotor, Vicente
supporting information; experimental part, p. 2858 - 2862 (2011/05/12)
An enzymatic study has been performed in the search for synthetic routes to produce chloramphenicol derivatives through regioselective processes using lipases. Complementary transesterification and hydrolytic reactions have been carried to synthesize chloramphenicol regioisomers. Reaction parameters, such as biocatalyst, solvent, acyl donor, and temperature have been optimised in order to obtain chloramphenicol esters with high yields through acylation processes. Scale-up of the enzymatic reactions (1 g-scale at 0.25 M) and catalyst recycling (up to 10 cycles) have been successfully achieved. Furthermore, monoacylated derivatives at the more hindered secondary position could also be obtained employing hydrolysis processes.
Isolation of 3' -O-acetylchloramphenicol: a possible intermediate in chloramphenicol biosynthesis.
Gross, Frank,Lewis, Elizabeth A,Piraee, Mahmood,van Pee, Karl-Heinz,Vining, Leo C,White, Robert L
, p. 283 - 286 (2007/10/03)
3' -O-acetylchloramphenicol, commonly formed from chloramphenicol by resistant bacteria, has been isolated from the antibiotic-producing organism. Biosynthetic experiments suggest that it is a protected intermediate in chloramphenicol biosynthesis, implicating acetylation as a self-resistance mechanism in the producing organism.
REGIOSELECTIVE ACYLATIVE CLEAVAGE OF CYCLIC FORMAL OF CHLORAMPHENICOL
Hazra, B. G.,Pore, V. S.,Maybhate, S. P.,Natekar, M. V.,Rao, A. S.
, p. 1763 - 1770 (2007/10/02)
The amide 6 has been synthesised by reacting the amine 3 with dichloroketene in situ.This amide 6 on nitration gave formal 7, which when reacted with acetic anhydride and p-toluene sulfonic acid underwent regioselective cleavage of the dioxane ring to furnish the hemiacetal 11.This on treatment with methanol-water-ammonia yielded chloramphenicol 2.
