Solid-phase synthesis and dimerization of an azobenzene-containing peptide as photoisomerizable proteinase inhibitor |
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Authors: | Paolo Rovero Stefano Pegoraro Stefania Viganò Cristina Amato Lucia Vaccari Ettore Balestreri and Romano Felicioli |
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Institution: | (1) Institute of Mutagenesis and Differentiation, CNR Peptide Synthesis Laboratory, Via Syezia 2A, I-56124 Pisa, Italy;(2) Department of Physiology, Università, I-56100 Pisa, Italy;(3) Department of Biochemistry, Università, I-56100 Pisa, Italy;(4) Institute of Biophysics, CNR, Via S. Lorenzo 26, I-56127 Pisa, Italy |
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Abstract: | Summary The synthesis and biological activity of a photochromic compound, in which two Lys2 dipeptides are linked through their N-terminal amino groups by an azobenzene moiety, are reported. The synthesis was achieved by a novel solid-phase dimerization strategy, based on the reaction of 4,4 -azobenzene dibenzoyl chloride with two N-terminal amino groups of distinct Lys2 dipeptides directly on the resin. Both the trans form and the photostationary state mixture (59% cis and 41% trans) inhibit a plant proteinase which is known to be sensitive to polycationic compounds. |
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Keywords: | Azobenzene Dimerization Photoisomerization Proteinase inhibitors |
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