An Alternate Synthesis of Leupeptins and Their Analogs

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It was found that lithium aluminum hydride reduction of N^a, N^G-disubstituted arginine lactam (3a-c) at a low temperature gave a corresponding argininal derivative (4a-c). Analogous reduction of acetyl-L-leucyl-L-leucyl-N-benzyloxycarbonyl-L-arginine lactam (8b) or its dipeptide analog (13) yielded leupeptin Ac-LL(1a) or acetylleucyl-argininal (11) respectively. Antiplasmin activities of these synthetic leupeptins were also reported.

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