Natural products serve as a rich reservoir of bioactive molecules and have therefore been significantly exploited by humans over millennia, perhaps most markedly in modern medicine. The biosynthetic enzymes that serve to assemble these complex molecules are also of high interest, from both a fundamental perspective and for their biotechnological potential. The derivatization of complex natural products, which is sought to elucidate and tune bioactivity, is often challenging using synthetic chemistry, while enzymatic and engineering approaches provide attractive alternatives. In this research talk, I will present methods of diversifying jadomycin-type angucycline antibiotics, natural products produced by Streptomyces venezuelae. Further, I will discuss the characterization a GT1 family glycosyltransferase found to catalyze the transfer of D-glucose to a diverse set of substrates.