Biosynthetic studies using 18O isotope shifts in 13C nuclear magnetic resonance

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Abstract
Isotopic substitution with oxygen-18 induces an observable upfield shift in the 13C nmr positions of directly-attached carbons, and in some cases, β-carbons. The magnitudes of these shifts range from about 0.05 ppm to 0.01 ppm, and are dependent on structure in an empirically predictable fashion. Incorporation of doubly labeled (13C, 18O) precursors into polyketides followed by 13C nmr analysis can identify carbon–oxygen bonds remaining intact during microbial biosynthesis. This technique has been applied to studies on antibiotics such as brefeldin A, cytochalasin B, granaticin, and lasalocid A, as well as aflatoxin precursors such as averufin, versicolorin A, and sterigmatocystin.

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