کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1364372 | 981535 | 2008 | 4 صفحه PDF | دانلود رایگان |
![عکس صفحه اول مقاله: Possible involvement of radical intermediates in the inhibition of cysteine proteases by allenyl esters and amides Possible involvement of radical intermediates in the inhibition of cysteine proteases by allenyl esters and amides](/preview/png/1364372.png)
In order to investigate crystallographically the mechanism of inhibition of cysteine protease by α-methyl-γ,γ-diphenylallenecarboxylic acid ethyl ester 3, a cysteine protease inhibitor having in vivo stability, we synthesized N-(α-methyl-γ,γ-diphenylallenecarbonyl)-l-phenylalanine ethyl ester 4. Reaction of 4 with thiophenol, the SH group of which has similar pKa value to that of cysteine protease, produced oxygen-mediated radical adducts 6 and 7 in ambient air but did not proceed under oxygen-free conditions. Catalytic activities of two thiol enzymes including cathepsin B were also lowered in the absence of oxygen. These results suggest that cysteine protease can act through an oxygen-dependent radical mechanism.
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Journal: Bioorganic & Medicinal Chemistry Letters - Volume 18, Issue 23, 1 December 2008, Pages 6202–6205