4-Acetamidophenyl esters and 4-acetamidoanilides of L-arginine,p-guanidino-L-phenylalanine, L-lysine, N2-[D-fructos-3-O-yl and D-glucos-3-O-yl]acetyl-L-lysine as potential acrosin inhibitors☆

Add time:08/15/2019    Source:sciencedirect.com

Syntheses of4-acetamidophenyl esters and 4-acetamidoanilides of L-lysine,p-guanidino-L-phenylalanine,L-leucyl-L-lysine, L-leucyl-L-leucyl-L-lysine, N2-[(1,2-O-isopropylidene-α-D-glucofuranos-3-O-yl)acetyl]-L-lysine, N2-[(1,2-O-isopropylidene-β-D-fructopyranos-3-O-yl)acetyl]-L-lysine are reported. 4-Acetamidophenyl L-argininate was too unstable to be isolated but L-arginin-4-acetamidoanilide was prepared. These amino acid and peptide derivatives proved to be enantiomerically pure and were characterized by their 1H and 13C chemical shifts which were established by means of multipulse 1D and 2D NMR techniques. Preliminary evaluation showed these compounds to be relatively weak inhibitors of human acrosin and bovine trypsin.

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