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

doi:10.1016/S0960-894X(01)00464-4

Bioorganic & Medicinal Chemistry Letters

Volume 11, Issue 18, 17 September 2001, Pages 2441-2444

https://doi.org/10.1016/S0960-894X(01)00464-4 Get rights and content

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.

Incorporation of an azobenzene into a dipeptide chain (see 3) gave a ‘slow-tight binding’ inhibitor, while the introduction of a carbamate linker (see 4) gave a modest enhancement in photoswitching of enzyme activity for the photostationary state enriched in the (Z)-isomer over the (E)-isomer.

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Acknowledgments

This work was supported by a research grant from the Royal Society of New Zealand Marsden Fund.

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

Abstract

Section snippets

Acknowledgments

Biochem. Biophys. Res. Commun.

J. Med. Chem.

J. Am. Chem. Soc.

J. Am. Chem. Soc.

Science

Angew. Chem., Int. Ed. Engl.

J. Am. Chem. Soc.

J. Am. Chem. Soc.

React. Poly.

Tetrahedron

J. Am. Chem. Soc.