Journal
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
Volume 95, Issue 12, Pages 1775-1785Publisher
CHEMICAL SOC JAPAN
DOI: 10.1246/bcsj.20220253
Keywords
Configurational assignment; Macrolides; NMR calculation
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Funding
- Chuo University Grant for Special Research
- Research Center for Computational Science at Okazaki in Japan [22-IMS-C015]
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In this study, the application of GIAO NMR chemical shift calculation and DP4-type statistical analyses in the stereochemical assignment of marine macrolide natural products was assessed. The incorrect relative configurations in the originally proposed structures were identified and the effect of cumulative Boltzmann population level on DP4+ probability was examined. Additionally, the GIAO NMR chemical shift calculation/DP4-type statistical analysis was successfully applied to the determination of the relative configuration of leptolyngbyalide A-C/oscillariolide macrolactone.
The stereochemical assignment of marine macrolide natural products by quantum chemical calculations is often hampered by the generation of an intractable number of conformers in molecular mechanics conformation searches. In this study, we assessed in detail the application of GIAO NMR chemical shift calculation and DP4-type statistical analyses to the stereochemical assignment of two marine macrolide natural products, whose relative configurations had been incorrectly assigned in the originally proposed structures. We also examined how DP4+ probability was affected by cumulative Boltzmann population level of molecular mechanics-derived conformers. Finally, GIAO NMR chemical shift calculation/DP4-type statistical analysis was applied to leptolyngbyalide A-C/oscillariolide macrolactone, whose relative configuration has not been assigned so far.
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