In nature,
only one enzyme — bacterial nitrogenase — can achieve the same reaction, but without emitting excess
nitrogen compounds into the environment, or in other words, leaching of nitrates into groundwater.
Similarly, in the oxazole series,
compound 153 was
only moderately active (IC50 = 2.83 μM), whereas substitution at carbon adjacent to the
nitrogen atom resulted in a potent
compound 154 (IC50 = 7.2 nM).