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KMID : 0043320140370080967
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Archives of Pharmacal Research
2014 Volume.37 No. 8 p.967 ~ p.971
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Application of 13C-labeling and 13C-13C COSY NMR experiments in the structure determination of a microbial natural product
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Kwon Yun
Park Sung-Hyouk
Shin Jong-Heon
Oh Dong-Chan
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Abstract
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The elucidation of the structures of complex natural products bearing many quaternary carbons remains challenging, even in this advanced spectroscopic era. 13C-13C COSY NMR spectroscopy shows direct couplings between 13C and 13C, 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 13C-based NMR experiments, due to the low natural abundance of the 13C nucleus, is problematic when applying these techniques. Our efforts in the 13C labeling of a microbial natural product, cyclopiazonic acid (1), by feeding 13C-labeled glucose to the fungal culture, enabled us to acquire 13C-13C COSY NMR spectra on a milligram scale that clearly show the carbon backbone of the compound. This is the first application of 13C-13C COSY NMR experiments for a natural product. The results suggest that 13C-13C COSY NMR spectroscopy can be routinely used for the structure determination of microbial natural products by 13C-enrichment of a compound with 13C-glucose.
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KEYWORD
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13C-13C COSY, 13C-labeling, Structure elucidation, Natural product, Microorganism
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