RESUMO
A set of 17,600 samples belonging to our compound collection is selectively examined by liquid chromatography with UV, evaporative light scattering, and mass spectrometric detection methods. At least 70% of this set consists of pure samples with the expected structures. Subsequent studies by flow injection mass spectrometry show that this value is a conservative estimate and that the actual percentage of pure and correct compounds is close to 80%. Because this is the first time that sample quality information becomes available on such a large scale for the compound collection, it offers an opportunity to perform chemi-informatic studies for which structural integrity is essential. Results of these studies can be used to improve the selection of compounds for screening and evaluate the quality of compounds from particular sources.
Assuntos
Cromatografia Líquida de Alta Pressão/métodos , Preparações Farmacêuticas/análise , Análise de Injeção de Fluxo , Luz , Espectrometria de Massas , Espectrofotometria UltravioletaRESUMO
O-Demethylpaulomycin A (C33H44N2O17S), O-demethylpaulomycin B (C32H42N2O17S), paulomenol A (C29H43NO16), paulomenol B (C28H41NO16), and the hydrogen sulfide adducts of paulomycin A (U-77,802, C34H48N2O17S2), and paulomycin B (U-77,803, C33H46N2O17S2) have been isolated from fermentations of Streptomyces paulus strain 273. The structure of these compounds was determined by 1H and 13C NMR and fast atom bombardment mass spectrum spectroscopic techniques and degradative studies. The antibacterial properties of these new metabolites, which are related to paulomycins A and B (J. Antibiotics 35: 285-294, 1982), are briefly discussed.
Assuntos
Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Fenômenos Químicos , Química , Cromatografia Líquida de Alta Pressão , Cicloexenos , Dissacarídeos/isolamento & purificação , Dissacarídeos/farmacologia , Fermentação , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Staphylococcus aureus/efeitos dos fármacos , Streptococcus/efeitos dos fármacos , Streptomyces/metabolismoRESUMO
Senfolomycins A and B (Antimicrob. Agents Chemother.-1965: 828-831, 1966) are two antibacterial agents with physico-chemical and biological properties similar to those of paulomycin. Recent studies indicate that senfolomycin A (C29H36N2O16S, MW 700) has molecular composition and fast atom bombardment MS fragmentation pattern identical to those of paulomycin E. Extensive NMR work indicates that the two antibiotics, which have been separated by HPLC and TLC, differ only in the stereochemistry of the OCH3 group present in their respective sugar moieties. Indirect evident suggests that senfolomycin B is dihydrosenfolomycin A (C29H38N2O16S, MW 702) and in this respect it is related to paulomycin F. The proposed structures for senfolomycins A and B are discussed.
Assuntos
Antibacterianos , Benzoquinonas , Fenômenos Químicos , Química , Cromatografia Líquida de Alta Pressão , Cicloexenos , Dissacarídeos/isolamento & purificação , Dissacarídeos/farmacologia , Enterococcus faecalis/efeitos dos fármacos , Isotiocianatos , Estrutura Molecular , Staphylococcus aureus/efeitos dos fármacos , Staphylococcus epidermidis/efeitos dos fármacos , Streptococcus pneumoniae/efeitos dos fármacos , Relação Estrutura-AtividadeRESUMO
Paulomycin A2 (C34H46N2O17S), paulomycin C (C32H42N2O17S), paulomycin D (C31H40N2O17S), paulomycin E (C29H36N2O16S) and paulomycin F (C29H38N2O16S) have been isolated from fermentations of Streptomyces paulus strain 273. The structure of these compounds was determined using NMR and mass spectroscopic techniques. The new paulomycins, like paulomycins A and B (J. Antibiotics 35: 285-294, 1982) are highly active mainly against Gram-positive organisms.
Assuntos
Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Fenômenos Químicos , Química , Cromatografia Líquida de Alta Pressão , Cicloexenos , Dissacarídeos/isolamento & purificação , Dissacarídeos/farmacologia , Bactérias Gram-Positivas/efeitos dos fármacos , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Testes de Sensibilidade MicrobianaRESUMO
Arginomycin is a new nucleoside antibiotic produced by Streptomyces arginesis. Arginomycin, C18H28N8O5, which inhibits the growth of Gram-positive bacteria and fungi in vitro, is structurally related to blasticidin S and found to be relatively non-toxic.
Assuntos
Aminoglicosídeos , Streptomyces/metabolismo , Animais , Antibacterianos , Fenômenos Químicos , Química , Cromatografia , Fungos/efeitos dos fármacos , Bactérias Gram-Positivas/efeitos dos fármacos , Dose Letal Mediana , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Camundongos , Nucleosídeos/biossíntese , Nucleosídeos/isolamento & purificação , Nucleosídeos/farmacologia , EspectrofotometriaRESUMO
Paldimycin (antibiotic 273a1) and antibiotic 273a2 as well as their individual components, paldimycins A (273a1 alpha) and B (273a1 beta) and antibiotics 273a2 alpha and 273a2 beta were synthesized from paulomycin, paulomycin A and paulomycin B, respectively, by reacting with N-acetyl-L-cysteine. The semisynthetic antibiotics had chromatographic behavior (TLC, HPLC) and physical and chemical properties identical to the properties of the corresponding antibiotics produced by Streptomyces paulus.
