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- Title
Application of C-labeling and C-C COSY NMR experiments in the structure determination of a microbial natural product.
- Authors
Kwon, Yun; Park, Sunghyouk; Shin, Jongheon; Oh, Dong-Chan
- Abstract
The elucidation of the structures of complex natural products bearing many quaternary carbons remains challenging, even in this advanced spectroscopic era. C-C COSY NMR spectroscopy shows direct couplings between C and C, which comprise the backbone of a natural product. Thus, this type of experiment is particularly useful for natural products bearing consecutive quaternary carbons. However, the low sensitivity of C-based NMR experiments, due to the low natural abundance of the C nucleus, is problematic when applying these techniques. Our efforts in the C labeling of a microbial natural product, cyclopiazonic acid ( 1), by feeding C-labeled glucose to the fungal culture, enabled us to acquire C-C COSY NMR spectra on a milligram scale that clearly show the carbon backbone of the compound. This is the first application of C-C COSY NMR experiments for a natural product. The results suggest that C-C COSY NMR spectroscopy can be routinely used for the structure determination of microbial natural products by C-enrichment of a compound with C-glucose.
- Publication
Archives of Pharmacal Research, 2014, Vol 37, Issue 8, p967
- ISSN
0253-6269
- Publication type
Article
- DOI
10.1007/s12272-013-0254-8