2005
DOI: 10.1073/pnas.0508425102
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Stereostructure of luminamicin, an anaerobic antibiotic, via molecular dynamics, NMR spectroscopy, and the modified Mosher method

Abstract: The absolute stereostructure of luminamicin, an anaerobic antibiotic, has been determined by using conformational analysis via high-temperature molecular dynamics, NMR spectroscopy, and the modified Mosher method. It was found that luminamicin has the S, S, R, R, R, R, S, S, S, R, and S configurations at C2, C4, C7, C9, C10, C11, C12, C13, C16, C28, and C29, respectively. This configuration is the same as that found in nodusmicin, which has a chemical structure quite similar to luminamicin. The structure of lu… Show more

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Cited by 19 publications
(10 citation statements)
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“…89 Compound 122 showed selective activity against anaerobic and microaerophilic bacteria whereas compounds 118 and 119 inhibited some aerobic bacteria, thereby suggesting the importance of the additive macrocyclic moiety. 90 The biosynthetic origin of this family was investigated through feeding experiments, as shown for compound 122 in Fig. 4.…”
Section: Macrolidesmentioning
confidence: 99%
“…89 Compound 122 showed selective activity against anaerobic and microaerophilic bacteria whereas compounds 118 and 119 inhibited some aerobic bacteria, thereby suggesting the importance of the additive macrocyclic moiety. 90 The biosynthetic origin of this family was investigated through feeding experiments, as shown for compound 122 in Fig. 4.…”
Section: Macrolidesmentioning
confidence: 99%
“…Moreover, the existence of a double bond between the shielded quaternary C-2 at δ C 89.2 and C-3 in compound 1 could be confirmed by the COSY and HMBC correlations with the hydroxylated methine unit on C-4 at δ H 5.71, d (J = 2.8 Hz) and δ C 107.0, as well as with the C-4 OH singlet at 6.50 ppm, as shown in Figure 2 (Figures S4 and S6). By modifying the Mosher method [23], the absolute stereochemistry on C-4 was established to have the R configuration (Figure S7). Compound 1 was derivatized with chiral reagents Rand S-methoxy-α-(trifluoromethyl)phenylacetyl chloride (MTPA-Cl).…”
Section: Resultsmentioning
confidence: 99%
“…However, the chirality of the stereocentres located in the long acyclic part of BA, at C‐16 and C‐19, could not be assigned on the basis of the previous analysis. A possible solution for this problem is based on the results of a molecular‐mechanics approach to determine the relative configuration of these chiral centres in combination with NMR data 1315…”
Section: Resultsmentioning
confidence: 99%