New Acyloxymethyl Ketones: Useful Probes for Cysteine Protease Profiling
Peptidyl-acyloxymethyl ketones (AOMKs) belong to a class of selective, irreversible inhibitors (activity-based probes) widely used as chemical tools of investigating proteins, for example, in activity-based protein profiling. The synthesis of the AOMKs has always been challenging and current methodologies involve both solution and solid-phase synthesis. Herein, the synthesis of a new scaffold useful for the preparation of peptidyl-AOMKs is reported and it is demonstrated that the new synthetic probes bearing a 4-functionalized 2,6-dimethylbenzoate efficiently inhibit cysteine proteases like cathepsin B.
Stereospecific syntheses of 2-alkyl and 2-phenyl substituted 3-(2,6-dimethyl-4-hydroxyphenyl)propanoic acids
Stereospecific syntheses of 2-methyl-, 2-ethyl-, 2-cyclohexyland 2-phenyl- substituted 3-(2,6-dimethyl-4-hydroxyphenyl)propanoic acids were developed. The key steps for the formation of the stereogenic centers involved the utilization of Evans' 4-benzyl-2-oxazolidinone chiral auxiliary. These compounds were designed to replace the N-terminal tyrosine residue in opioid peptides.
Lu,Schiller
p. 1639 - 1644
(2007/10/03)
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