(86f) Discovery of Novel Compounds and Pathways through Identification of Bioprivileged Molecules

Bioprivileged molecules are biology-derived chemical intermediates that can be efficiently converted to a diversity of chemical products including both novel molecules and drop-in replacements. Bridging chemical and biological catalysis by bioprivileged molecules provides a useful and flexible new paradigm for producing biobased chemicals. However, the discovery of bioprivileged molecules has been demonstrated to require extensive experimental effort over a long period of time. To meet this need, we developed a computational framework for identification of candidate bioprivileged molecules from C₆H_xO_y (C6), C₄H_xO_y (C4), C₅H_xO_y (C5), and C₇H_xO_y (C7) molecule subspaces that ranks the molecules according to a number of diverse criteria and generates products emanating from them using automated reaction network generation. All top candidates were analyzed for their key functional moieties using a random forest model, and this algorithm was applied to compare the functional group space occupied by bioprivileged molecules of various databases of molecules with a focus on evaluating how closely the molecules were aligned with those known to biology. The framework is sufficiently automated and flexible that it can be easily expanded to include other chemical formulae to screen for bioprivileged candidates. This in turn facilitates the retrosynthesis process inherent in the framework to identify those bioprivileged intermediates in other subspaces that lead to target molecules. The application to discovery of known and novel monomers for poly(hydroxyurethanes) that are derived from biobased molecules and lead to recyclable materials will be discussed.