Sulfur-containing antibiotics

Closely related to the penicillins are the cephalosporins, a group of /3-lactam antibiotics that contain an unsaturated six-membered, sulfur-containing ring. Cephalexin, marketed under the trade name Keflex, is an example. Cephalosporins generally have much greater antibacterial activity than penicillins, particularly against resistant strains of bacteria. 

Also at Oxford, Abraham and Newton discovered the first cephalosporin, cephalosporin C, as a product of Acremonium chrysogenum (Cephalosporium acremonium).17 This new, sulfur-containing antibiotic was also a (5-lactam but the fused, sulfur-containing ring is a six-membered dihydrothiazine. 

Thiopeptin is a sulfur-containing peptide antibiotic complex produced by Streptomyces tateyamensis. It is composed of five closely related components, the thiopeptins Ai, A2, A3, A4, and B (8). Commercially available thiopeptin is primarily composed of thiopeptins B. This antibiotic is active against gram-positive bacteria and is used exclusively as a feed additive for pigs. 

Lactam Antibiotics, Other Sulfur-containing Natural Products, and Related Compounds , J. G. Gleason and W. D. Kingsbury, in Organic Compounds of Sulphur, Selenium and Tellurium , ed. D. R. Hogg, Royal Society of Chemistry, London, 1979, vol. 5, pp. 454-480. 

Because of concern about resistance transfer, however, there is a growing attempt to supplant these drugs with new compounds, such as the sulfur-containing peptide antibiotic... 

The cephalosporins are antibiotics produced by the bacterial strain cephalosporium. They are closely related to the penicillins. Thus cephalosporin C has a /3-lactam ring but a six-membered sulfur-containing ring ... 

Arene oxides and their oxepin tautomers play a role in the biosynthesis of some microbial metabolites, e.g., the sulfur-containing antibiotics gliotoxin (345),188 dehydrogliotoxin (346),189 apoarontin (347),190 aranotin (348),191... 

JNuesch, J Heim, HJ Treichler. The biosynthesis of sulfur-containing beta-lactam antibiotics. Annu Rev Microbiol 41 51-75, 1987. 

Pulse amperometric detection (PAD) has been used for the detection on a PDMS chip. This method is useful for analysis of underivatized compounds, such as carbohydrates, amino acids, and sulfur-containing antibiotics, which easily caused electrode fouling. In PAD, a high positive potential (1.4-1.8 V) is first applied in order to clean the electrode (e.g., Au) surface. This is followed by a negative potential step (-0.5 V) to reactivate the electrode surface. A third moderate potential (+0.5 to +0.7 V) is applied for detection of the target analyte [752]. 

NH4)6Mo7024 supported on a cross-linked polystyrene has also been used for the selective oxidation of sulfur-containing compounds with H2O2 (209, 262). An example of interest is the selective conversion of penicillin G to the sulfoxide, an important intermediate for cephalosporin antibiotics ... 

Only fully saturated six-membered rings are really chairs or boats. Even with one double bond in the ring, the ring is partly flattened here we will look at ail even flatter example. A unique antibiotic has been discovered in China and called chuangxinmycin (meaning a new kind of mycin where mycin -antibiotic). It is unique because it is a sulfur-containing indole few natural products and no other antibiotics have this sort of structure. 

Sparsomydn inhibits protein synthesis in all organisms and consequently is not used as an antibiotic. However, it has been tested extensively for its antitumor activity [49]. Sparsomycin contains a pseudouracil base with a conjugated link to a sulfur containing tail (Fig. 4.11). This chemical structure has been compared with that of puromycin, and it has been su ested that sparsomycin binds to the A-site much like puromycin [50]. Sparsomycin does not bind to the ribosome unless a P-site substrate is also present. 

Prontosil and other sulfur-containing antibiotics are collectively called sulfa drugs. Prontosil is not the active agent itself. In cells, it is metabolized to sulfanilamide, the active drug. To under-... 

La Course, W.R. Dasenbrock, C.O. Pulsed electrochemical detection of sulfur-containing antibiotics following high performance liquid chromatography. J. Pharm. Biomed. Anal. 1999, 19, 239-252. 

In addition to quite a few sulfur-containing amino acids, many sulfur containing organic natural products exhibiting notable biological activities are known to date, such as the vitamin biotin, the Allium components which are responsible for the characteristic taste and smell of onion, garlic, and related plants, the antibiotic penicillins and lincomycins as well as the... 

Sparsomycin, a sulfur-containing antibiotic, inhibits protein synthesis in mammalian and bacterial cells. Tryptophan administration before or after sparsomycin did not affect the hepatic polyribosomal disaggregation or the decreased protein synthesis due to sparsomycin.188 A possible explanation for the lack of effect by tryptophan may be due to sparsomycin s ability to cause fall-off ribosomes, which are defective as indicated by the decreased formation of polyphenylalanine when assayed in vitro with poly(U).207... 

Thiopeptide antibiotics, thiazolyl peptides, naturally occurring sulfur-containing, highly modified, macrocyclic peptides. They share a number of structural motifs, including several heterocycles such as thiazoles, a dehydropiperidine, a pyridine, oxazoles, and indoles. Nearly aU of the thiopeptide antibiotics act as inhibitors of protein synthesis in bacteria. They are secondary metabolites produced by actino-mycetes, largely by the genus Streptomyces. A representative member of this family is thiostrepton [M. C. Bagleyetal., Chem. Rev. 2005, 105, 685]. 

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