Abstract
Enantiomerically pure ω-borono-α-amino acids of various chain lengths have been synthesized according to a general methodology involving condensation of alkenyl and alkynyl bromides with NiII complex of the Schiff base derived from glycine and (S)-2-[N′-(N-benzylprolyl)amino]benzophenone, hydroboration of the intermediate ω-unsaturated α-amino acids with diisopinocampheylborane, and oxidation with acetaldehyde. Some of these compounds act as potent inhibitors of rat liver and murine macrophage arginases, demonstrating that distance between the B(OH)2 and α-amino acid groups is a key determinant for their interaction with arginase. In contrast, they are without effect on neuronal and inducible NO synthases.
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