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Please use this identifier to cite or link to this item: http://hdl.handle.net/10805/1028

Title: Synthesis and elaboration of peptidomimetic units
Authors: RAMADORI, FEDERICO
Tutor: Pellacani, Lucio
Fioravanti, Stefania
Keywords: Peptidomimetics
Amino acids
Malonamides
Knoevenagel reaction
gem-diaminic units
aziridine
amination reaction
Suzuki coupling
Issue Date: Dec-2010
Abstract: Retro-peptides are peptidomimetics that present the direction of the amino acidic sequence reversed. A classical retro modification can be obtained by the introduction of the malonyl unit followed by a gem-diaminic unit, that can result in an increase of proteolysis resistance of the related parent peptide, retarding degradation and consequently enhancing therapeutic efficacy.This thesis aims at developing synthetic stategies to synthesize new interesting building blocks for the construction of peptidomimetics containing a retro modification.In this field Meldrum’s acid is recently reported as a useful scaffold to obtain non-symmetric disubstituted malonamides rAA-mGly-AA′ as building blocks for the synthesis of retro-peptides. The attention has been turned towards the synthetic elaboration of different rAA-mGly-AA′ with the aim of introducing, into the malonamide backbone, the olefinic moiety by a Knoevenagel condensation, obtaining correspondig malonyl dehydro peptides MDHPs.The investigation of a further elaboration was carried out to obtain the corresponding epoxy and aziridino peptides,interesting building blocks containing electrophilic sites known to react with nucleophilic amino acids within the active site of proteases. Starting from L-amino acids, a new methodology is presented for the synthesis of gem-diaminic units g-AA that replace the sense of direction of amino acids in retro-peptide chain.In the field of amino acid and peptide modifications by palladium catalysed reactions, in the University of Bath a methodology has been developed to synthesise biphenyl lysine derivatives by a two step procedure, where the key step involves a Suzuki cross-coupling reaction.
URI: http://hdl.handle.net/10805/1028
Research interests: Organic Chemistry
Appears in PhD:SCIENZE CHIMICHE

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