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 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-m Delta(2)AAaEuro(3)-AA', partially modified retro peptides characterized by an interesting combination of retro and dehydro modifications in the same structure.
Short malonyl dehydro peptides as potential scaffolds for peptidomimetics by an efficient Knoevenagel reaction / Fioravanti, Stefania; Gasbarri, Simona; Morreale, Alberto; Pellacani, Lucio; Ramadori, Federico; Tardella, Paolo Antonio. - In: AMINO ACIDS. - ISSN 0939-4451. - STAMPA. - 39:2(2010), pp. 461-470. [10.1007/s00726-009-0462-1]
Short malonyl dehydro peptides as potential scaffolds for peptidomimetics by an efficient Knoevenagel reaction
FIORAVANTI, Stefania;GASBARRI, SIMONA;MORREALE, Alberto;PELLACANI, Lucio;RAMADORI, FEDERICO;TARDELLA, Paolo Antonio
2010
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 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-m Delta(2)AAaEuro(3)-AA', partially modified retro peptides characterized by an interesting combination of retro and dehydro modifications in the same structure.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
