Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 17, Issue 42, Pages 11868-11875Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201101129
Keywords
circular dichroism; configuration determination; desulfurization; natural products; vibrational spectroscopy
Categories
Funding
- Cancer Research UK [C21484A6944]
- BBSRC [BB/C510859/1]
- BBSRC [BB/G009619/1] Funding Source: UKRI
- MRC [G0501164] Funding Source: UKRI
- Biotechnology and Biological Sciences Research Council [BB/G009619/1] Funding Source: researchfish
- Cancer Research UK [13086] Funding Source: researchfish
- Medical Research Council [G0501164] Funding Source: researchfish
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Isolation and semisynthetic modification of the fungal metabolite chaetocin gave access to a desulfurized analogue of this natural product. Detailed chiroptical studies, comparing experimentally obtained optical rotation values, electronic circular dichroism spectra, and vibrational circular dichroism spectra to computationally simulated ones, reveal the desulfurization of chaetocin to unambiguously proceed with retention of configuration. Consideration of the plausible mechanisms for this process highlighted inconsistencies in the stereochemical assignment of related molecules in the literature. This in turn allowed the stereochemical reassignment of the natural product analogue dethiodehydrogliotoxin.
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