Antibiotic SB22484: A novel complex of the aurodox group. II. Structure elucidation of the four factors
| Autor: | Duncan M. F. Edwards, Pietro Ferrari, Gian Gualberto Gallo, Enrico Selva |
|---|---|
| Rok vydání: | 1990 |
| Předmět: |
Acid-Base Equilibrium
Pharmacology Magnetic Resonance Spectroscopy Anomer Molecular Structure Spectrophotometry Infrared Stereochemistry Molecular Conformation Stereoisomerism Nuclear magnetic resonance spectroscopy Hydrogen-Ion Concentration Mass Spectrometry chemistry.chemical_compound chemistry Drug Discovery Spectrophotometry Ultraviolet Epimer Ethyl group Aurodox Two-dimensional nuclear magnetic resonance spectroscopy Chromatography High Pressure Liquid Acetamide Chromatography Liquid Methyl group |
| Zdroj: | The Journal of Antibiotics. 43:1359-1366 |
| ISSN: | 1881-1469 0021-8820 |
| DOI: | 10.7164/antibiotics.43.1359 |
| Popis: | SB22484, active against Neisseriae gonorrhoeae and Neisseriae meningitidis, is a complex of four factors, designed 1 through 4, which from two pairs of isomers, 1 and 3, and 2 and 4. Factors 1 and 3 account for 65% of the complex, factor 3 being the predominant one. On the basis of the existing and implemented correlations between structure and physico-chemical characteristics (UV and IR spectroscopies, ionization properties, MS as FAB and as negative and positive CI, 1H NMR spectroscopy as 2D COSY and NOESY) in the aurodox field, the complete structures were assigned. Factor 3 can be described as N-[7-[5(R)-[7-[1,2-dihydro-4-hydroxy-1H-2-oxo-3-pyridinyl]-6-methyl- 7-oxo-1(E),3(E),5(E)-heptatrienyl]tetrahydro-3(S),4(R)-dihydrox yfuran-2 (S)-yl]-6(S)-methoxy-5,7(R)-dimethyl-2(E),4(E)-heptadienyl]-alpha (S)-methyl-5(S)-methyltetrahydro-2(S),4(S or R)-dihydroxy-6(S)-[1(E), 3(Z)-pentadienyl]-2H-pyran-2-acetamide. Factor 1 is an epimer of factor 3 with the opposite configuration at the anomeric center. Factors 2 and 4 have an ethyl group instead of the methyl group alpha to the acetamide moiety and are in the same stereochemical relationship as the pair 1 and 3. |
| Databáze: | OpenAIRE |
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