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 K(i) of 10microM, and propenylphosphinate 2 and decylphosphinate 3 inhibited PepN with a K(i) of ca. 1microM. Sulfonate and sulfonamidate analogs did not inhibit PepN.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Aminopeptidases / antagonists & inhibitors*
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Bacterial Proteins / antagonists & inhibitors*
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Dipeptides / chemistry*
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Escherichia coli / enzymology*
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Phosphinic Acids / chemistry
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Phosphinic Acids / pharmacology
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Protease Inhibitors / chemistry*
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Protease Inhibitors / pharmacology*
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Sulfonamides / chemistry
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Sulfonamides / pharmacology
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Sulfonic Acids / chemistry
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Sulfonic Acids / pharmacology
Substances
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Bacterial Proteins
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Dipeptides
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Phosphinic Acids
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Protease Inhibitors
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Sulfonamides
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Sulfonic Acids
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pepN protein, Bacteria
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alanylalanine
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Aminopeptidases