Carbon-13 labeling strategies provide an important tool for organic chemists. Through enrichment of the carbon-13 isotope, organic substrates are easily traceable via nuclear magnetic resonance (NMR). This provides a method of evaluating reaction mechanisms, metabolic transformations and more. Methods to incorporate carbon isotopes are limited by access to affordable and reactive reagents. Our lab has optimized two name reactions to efficiently label aromatic substrates for use in biocatalysis discovery. The Rosenmund-von Braun reaction, using K13CN as the carbon-13 source has allowed for the successful labeling of a small library of molecules. In addition, the Negishi coupling reaction uses 13CH3I, a safer and cheaper source of carbon-13, also serves as an effective labeling strategy. With carbon-13 labeled substrates in hand, we have embarked on a discovery effort to identify new, biocatalyzed transformations through “feeding” labeled substrates to whole-cell bacterial cultures. The results of these efforts are reported.

Optimization of carbon-13 labeling strategies for new biocatalysis discovery

256th National Meeting (2018)

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