142181-87-1Relevant academic research and scientific papers
Synthesis and inhibiting properties toward trypsin like proteases of N(α)-(N,N-dimehtylcarbamoyl)-α-azaornitine and α-azalysine esters
Ferraccioli,Dalla Croce,Gallina,Consalvi,Scandurra
, p. 1517 - 1529 (2007/10/02)
N(α)-(N,N-dimethylcarbamoyl)-α-azaornithine and N(α)-(N,N-dimethylcarbamoyl)-α-azalysine phenyl and p-nitrophenyl esters (7-10) were synthesized and tested as inhibitors of trypsin, chymotrypsin and thrombin. The N,N-dimethylcarbamoyl group was chosen to decrease the tendency of acylcarbazates to cyclization into 1,3,4-oxadiazol-2(3H)-ones. Only the p-nitrophenyl α-azaornithine derivative 8 was inactivated rapidly by intramolecular acylation of the terminal amino group, rather than by cyclization to oxadiazolone, in aqueous solution at pH 8. The corresponding α-azalysine derivative 10 is completely unaffected under the same conditions. Rapid inactivation of thrombin and trypsin only was observed for all α-azapeptide esters 7-10 at 0.5 mM inhibitor concentration. No proteolytic activity was restored after 24 h following 2000 fold dilution of the inhibitor concentration suggesting formation of very stable acylenzymes.
