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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PieroniO. and FissiA., J. Photochem. Photobiol. B: Biol., 12 (1992) 125.
MartinekK. and BerzeinI.V., Photochem. Photobiol., 29 (1979) 637.
WestmarkP., KellyJ.P. and SmithB.D., J. Am. Chem. Soc., 115 (1993) 3416.
AmatoC., VaccariL., BalestreriE. and FelicioliR., J. Plant Physiol., 143 (1994) 274.
AmatoC., VaccariL., BalestreriE. and FelicioliR., Biochim. Biophys. Acta, 1249 (1995) 86.
AmatoC., FissiA., VaccariL., BalestreriE., PieroniO. and FelicioliR., J. Photochem. Photobiol. B: Biol., 28 (1995) 71.
TozziM.G., BalestreriE., CamiciM., FelicioliR. and IpataP.L., J. Agric. Food Chem. 29 (1981) 1075.
BradfordM.M., Anal. Biochem., 72 (1976) 248.
ErlangerB.F., KokowskiN. and CohenW., Arch. Biochem. Biophys., 95 (1961) 271.
HiguchiY., TakanoY., ShimazakiH., ShimoigashiY., KodamaH., MatsumotoH., NonakaS., SaitoR., WakiM. and KamiyaH., Eur. J. Pharmacol., 160 (1989) 413.
CheronisJ.C., WhalleyE.T., NguyenK.T., EubanksS.R., AllenL.G., DugganM.J., LoyS.D., BonhamK.A. and BlodgettJ.K., J. Med. Chem. 35 (1992) 1563.
DixonM. and WebbE.C., Enzymes, Longman, London, 1973, pp. 332–467.
LineweaverH. and BurkD., J. Am. Chem. Soc., 56 (1934) 658.
Cornish-BowdenA., Biochem. J., 137 (1974) 143.
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Rovero, P., Pegoraro, S., Viganò, S. et al. Solid-phase synthesis and dimerization of an azobenzene-containing peptide as photoisomerizable proteinase inhibitor. Lett Pept Sci 2, 27–32 (1995). https://doi.org/10.1007/BF00122920
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DOI: https://doi.org/10.1007/BF00122920