Phosphinate, sulfonate, and sulfonamidate dipeptides as potential inhibitors of Escherichia coli aminopeptidase N

KW Yang, FC Golich, TK Sigdel, MW Crowder

Index: Yang, Ke-Wu; Golich, Frank C.; Sigdel, Tara K.; Crowder, Michael W. Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 23 p. 5150 - 5153

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Citation Number: 15

Abstract

In an effort to prepare novel inhibitors of bacterial aminopeptidase N (PepN), the phosphinate, propenylphosphinate, decylphosphinate, sulfonate, and sulfonamidate analogs of Ala–Ala were synthesized and tested as inhibitors. Phosphinate 1 was shown to inhibit PepN with a Ki of 10μM, and propenylphosphinate 2 and decylphosphinate 3 inhibited PepN with a Ki of ca. 1μM. Sulfonate and sulfonamidate analogs did not inhibit ...