10.1021/jo00298a049
The research focuses on the synthesis and investigation of the reactivity of two phenanthroline-linked dihydronicotinamides, compounds 3 and 6, which serve as models for the NADH-alcohol dehydrogenase coenzyme-enzyme complex. The purpose of this study was to examine whether the metal ion in these models could mimic the function of catalytic zinc in alcohol dehydrogenase, specifically in binding the substrate near the dihydronicotinamide group, orienting the groups for hydride transfer, and activating the carbonyl group for reduction. The researchers concluded that the metal ion in these models, particularly when Zn2+ is present, could effectively mimic the catalytic function of zinc in the enzyme complex, with hydride transfer occurring within a ternary complex. Key chemicals used in the process include 1,4-dihydro-l-(l,l0-phenanthrolin-2-ylmethyl)-3-pyridinecarboxamide (3), 1,4-dihydro-N-(l,l0-phenanthrolin-2-ylmethyl)-l-(phenylmethyl)-3-pyridinecarboxamide (6), 2,4,6-trinitrobenzene sulfonate (TNBS), methylene blue (MB+), and 2-pyridinecarboxaldehyde (PyCHO), along with various metal ions (M2+ = Zn2+, Co2+, Ni2+, Mg2+, and Cd2+).