Bioorganic & medicinal chemistry letters

α-Ketoester-based photobiological switches: synthesis, peptide chain extension and assay against α-chymotrypsin

AJ Harvey, AD Abell

Index: Harvey, Andrew J.; Abell, Andrew D. Bioorganic and Medicinal Chemistry Letters, 2001 , vol. 11, # 18 p. 2441 - 2444

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Citation Number: 20

Abstract

The design, synthesis, photoisomerism and biological testing of two peptide-based photoswitchable inhibitors of α-chymotrypsin are presented. The use of a dipeptide recognition sequence gave a 'slow-tight binding'inhibitor, while the introduction of a carbamate linker to the azobenzene gave a modest enhancement in photoswitching of enzyme activity for the photostationary state enriched in the (Z)-isomer over the (E)-isomer.