Detail of "26049-94-5"

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The synthesis of lysylfluoromethanes and their properties as inhibitors of trypsin, plasmin and cathepsin B

The synthesis of lysylfluoromethanes and their properties as inhibitors of trypsin, plasmin and cathepsin B. Angliker, Herbert; Wikstrom, Peter; Rauber, Peter; Shaw, Elliott (Friedrich Miescher Inst., Basel CH-4002, Switz.In this study， 26049-94-5 and 9002-07-7 are also used.). Biochem. J., 241(3), 871-5 (English) 1987. CODEN: BIJOAK. ISSN: 0306-3275. DOCUMENT TYPE: Journal CA Section: 7 (Enzymes) Section cross-reference(s): 26 The synthesis of 2 lysylfluoromethanes is described by an extension of the synthesis method of P. Rauber, et al. (1986). Ala-Phe-Lys-Ch2F was found to be an active center-directed inhibitor of plasmin and trypsin, as is the corresponding chloromethane. However, the rate of covalent-bond formation was about an order of magnitude lower at 25° for the fluoro deriv. It was, in addn., an extremely effective inactivator of cathepsin B at pH 5.4 and 6.4. The chem. reactivity of fluoromethanes was compared with that of chloromethanes as alkylators of glutathione (GSH). At pH 7.4 and 37°, a fluoromethane had 1/500th the reactivity of a chloromethane. A comparison of the rates of reaction of the fluoromethane with cathepsin B and with GSH at pH 6.4 revealed an enhancement of 108-fold for the alkylation of the enzyme, ascribable largely to a proximity effect. .