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Triantaspirols A-C and Paraphaeolactone Cs from sp. KT4192: Sensitivity of CP3 in Distinguishing Close NMR Signals. | LitMetric

Triantaspirols A-C and Paraphaeolactone Cs from sp. KT4192: Sensitivity of CP3 in Distinguishing Close NMR Signals.

J Nat Prod

The United Graduate School of Agricultural Science, Iwate University, 18-8 Ueda 3 chome, Morioka, Iwate 020-8550, Japan.

Published: October 2024

Hybridized spirobisnaphthalene derivatives, triantaspirols A-C (-) and paraphaeolactones C1 and C2 ( and ), were identified from the culture broth of the fungus sp. KT4192. The NMR spectra of and , as well as and , closely resembled each other, indicating that these were pairs of diastereomers. Although this NMR spectral resemblance made it challenging to distinguish their relative configurations, detailed analysis of the electronic circular dichroism (ECD) spectra and NOE correlations allowed us to deduce them. The CP3 metric with the DFT-based NMR chemical shifts was found to distinguish configurations of diastereomers in a highly sensitive and accurate manner that DP4 could not account for because of the very close chemical shift differences in the experimental NMR spectra. The reliability of this method was assessed using 23 published examples which could not be distinguished by DP4 protocol.

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Source
http://dx.doi.org/10.1021/acs.jnatprod.4c00935DOI Listing

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