Natural products and their derivatives constitute a significant portion of clinical therapeutics. In an era of rapidly expanding antibiotic resistance among clinically problematic bacteria, the importance of novel natural compound discovery is paramount. Modern advancements in genomics has facilitated the discovery of ribosomally-encoded peptidic natural products and can be leveraged for the exploration of uncharacterized natural compound chemical space. Among these, the radical S-adenosyl methionine enzyme-tailored ribosomal peptides represent a significantly diverse and underexplored subclass of natural products. My bioinformatics-guided investigation of this group of peptides has the potential to uncover a broad range of new chemical structures that may be tested for activity as lead compound scaffolds as well as reveal fundamental natural product chemistry.