Short malonyl dehydro peptides as potential scaffolds for peptidomimetics by an efficient Knoevenagel reaction.
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 A 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)AA''-AA', partially modified retro peptides characterized by an interesting combination of retro and dehydro modifications in the same structure.
Fioravanti
Stefania
S
Dipartimento di Chimica, Università degli Studi di Roma La Sapienza, P.le Aldo Moro 5, 00185, Roma, Italy. stefania.fioravanti@uniroma1.it
Gasbarri
Simona
S
Morreale
Alberto
A
Pellacani
Lucio
L
Ramadori
Federico
F
Tardella
Paolo A
PA
D040761:Biomimetic Materials / Q000138:chemical synthesis*; D008314:Malonates / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis*
D008314:Malonates; D010455:Peptides