Biotransformation of antibiotics. I. Acylation of chloramphenicol by spores of Streptomyces griseus isolated from the egyptian soil.

Abstract

Incubation of spores, washed mycelium or whole cultures of a Streptomyces sp.

Unusual acylation of chloramphenicol in Lysobacter enzymogenes, a biocontrol agent with intrinsic resistance to multiple antibiotics

“…The singlet at δ 6.22 (−CHCl 2 ) and the complex resonance at δ 4.46 (m, H −2′) were identical to that of chloramphenicol. [38, 39] The DEPT experiment indicated the presence of one carbonyl group, suggesting compound 1 was a chloramphenicol ester. The acyl group was determined to be isobutyrate based on the molecular formula of compound 1 differing from that of chloramphenicol by C 4 H 7 O and the 1 H NMR doublet at δ 1.17 integrated to six protons.…”

“…The acyl group was determined to be isobutyrate based on the molecular formula of compound 1 differing from that of chloramphenicol by C 4 H 7 O and the 1 H NMR doublet at δ 1.17 integrated to six protons. The location of the isobutyrate group was determined at C-3′ hydroxyl based on the chemical shift of H-3′ at δ 3.5 in chloramphenicol has shifted to 4.30 and 4.42 ppm (Additional file 1: Table S1) [38, 39]. HRMS analysis gave a [M + Na] + of 415.0440 ( calc .…”

“…The study identified three unusual acyl derivatives of chloramphenicol and showed the involvement of a global regulator and a GNAT in the chloramphenicol resistance. Chloramphenicol binds the 50S ribosomal subunit in prokaryotic cells and inhibits peptidyl transferase during protein biosynthesis [39]. Many bacteria inactivate chloramphenicol by chloramphenicol acetyltransferase, which catalyzes the acetylation of the primary hydroxyl using acetyl-CoA as substrate, yielding chloramphenicol-3′-acetate (Fig.…”

Enzyme Catalyzed Synthesis of Some Vinyl Drug Esters in Organic Medium

“…[12] A few papers reported that the synthesis of the drug derivatives was catalyzed by enzymes. El-Kersh [13] reported the acyl derivatives of chlormaphenicol were obtained through biological catalysis. Ottolina [14] reported that the regioselective esterification of chloramphenicol and its synthetic analogue thiamphenicol has been achieved by the action of lipases in acetone.…”

A Chromosomal Gene for Chloramphenicol Acetyltransferase in Streptomyces acrimycini

“…Although this theory does not require the corresponding genes to be permanently plasmid-linked in their streptomycete hosts, the normal carriage of such genes on plasmids might have favoured their dissemination from such hosts to other bacteria. Of the antibiotic-inactivating enzymes coded by eubacterial plasmids, those catalysing acetylation or phosphorylation of aminoglycosides or acetylation of chloramphenicol are found in various streptomycetes (Benveniste & Davies, I 973 ; El- Kersch & Plourde, 1976a;Shaw & Hopwood, 1976;Nakano et al, 1977). However, nothing appears to be known in these organisms about the genetic determination of these enzymes because they have not been studied in genetically characterized strains.…”