Although boronic acids have attracted considerable interest as versatile intermediates in organic synthesis, their contributions in chemical biology and drug discovery programs have long been underestimated. This situation is changing since the beginning of the 2000s, mainly due to significant advances in modern organoborane chemistry and the recent FDA approval of Velcade®, a boropeptide used for multiple myeloma treatment. There is now a significant renewed interest in the design and synthesis of new boron-containing compounds. Due to their close analogy to their carbon counterparts, aminoboronic acids, alone or incorporated at the C-terminal position of a peptide, represent one of the major classes of organoboranes evaluated as potential drug candidates. This critical review aims to provide an overview of the current state of the art in their synthesis and their most relevant biological properties (156 references).