Antibiotic SB22484: a novel complex of the aurodox group. II. Structure elucidation of the four factors.
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.
Ferrari
P
P
MDRI--Lepetit Research Center, Gerenzano, Italy.
Edwards
D
D
Gallo
G G
GG
Selva
E
E
D000136:Acid-Base Equilibrium; D000899:Aurodox / Q000031:analogs & derivatives* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D002853:Chromatography, Liquid; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D015394:Molecular Structure; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D000899:Aurodox; C066792:SB 22484