Abstract
Non-symmetric disubstituted malonamides rAA-mGly-AA′, obtained from Meldrum’s acid, were considered as methylene active compounds and a Knoevenagel condensation methodology was developed involving piperidine and activated 4 Å molecular sieves as catalysts. The reaction is efficient, broad in scope, and easy to perform and allows access to E/Z mixtures of short malonyl dehydro peptides (MDHPs) rAA-mΔ2AA″-AA′, partially modified retro peptides characterized by an interesting combination of retro and dehydro modifications in the same structure.
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Italian MIUR and Università degli Studi di Roma “La Sapienza” are gratefully acknowledged for financial support (PRIN 2007FJC4SF_005).
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Fioravanti, S., Gasbarri, S., Morreale, A. et al. Short malonyl dehydro peptides as potential scaffolds for peptidomimetics by an efficient Knoevenagel reaction. Amino Acids 39, 461–470 (2010). https://doi.org/10.1007/s00726-009-0462-1
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DOI: https://doi.org/10.1007/s00726-009-0462-1