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Deacetoxycephalosporin C synthase from Streptomyces clavuligerus catalyses the conversion of the five-membered penicillin ring to the unsaturated six-membered cephem ring of deacetoxycephalosporin C. The effects on enzyme activity of the penicillin substrate sidechain and various cofactors were investigated using a continuous spectrophotometric assay. The conversion of penicillin G to phenylacetyl-7-aminodeacetoxycephalo sporanic acid (G-7-ADCA) was confirmed, and further details of the reaction were elucidated. The conversion of ampicillin to cephalexin was faster than that of acetyl-6-APA to acetyl-7-ADCA kcat = 0.120 +/- 0.001 s(-1) versus 0.035 +/- 0.001 s(-1), but they had similar Km values: 4.86 +/- 0.12 and 3.28 +/- 0.26 mM, respectively. Amoxycillin and penicillin V were also converted at low levels. Conversion was not detected for penicillanate, 6-aminopenicillanate, carbenicillin, temocillin, ticarcillin or benzylpenicilloic acid, suggesting that the enzyme has a relatively strict selectivity for the sidechain of the penicillin substrate.
online pharmacy ref source: www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=11437242&dopt=Abstract
Folia Microbiol (Praha). 2001;46(2):127-32.
Penicillin V production by Penicillium chrysogenum in the presence of Fe3+ and in low-iron culture medium.
Leiter E, Emri T, Gyemant G, Nagy I, Pocsi I, Winkelmann G, Pocsi I.
Department of Microbiology and Biotechnology, Faculty of Science, University of Debrecen, 4010 Debrecen, Hungary.
Late-exponential-phase Penicillium chrysogenum mycelia grown in a complex medium possessed an intracellular iron concentration of 650 mumol/L (2.2 +/- 0.6 mumol per g mycelial dry mass). This iron reserve was sufficient to ensure growth and antibiotic production after transferring mycelia into a defined low-iron minimal medium. Although the addition of Fe3+ to the Fe-limited cultures increased significantly the intracellular iron levels the surplus iron did not influence the production of penicillin V. Supplements of purified major P. chrysogenum siderophores (coprogen and ferrichrome) into the fermentation media did not affect the beta-lactam production and intracellular iron level. Neither 150 nor 300 mumol/L extracellular Fe3+ concentrations disturbed the glutathione metabolism of the fungus, and increased the oxidative stress caused by 700 mmol/L H2O2. Nevertheless, when iron was applied in the FeII oxidation state the oxidative cell injuries caused by the peroxide were significantly enhanced.
online pharmacy ref source: www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=11501399&dopt=Abstract
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