engleski

Novel cage-functionalized building blocks in peptidomimetic design

Synthetic peptides with antimicrobial activity are a very promising class of compounds for drug discovery. They are often prepared by changing the natural peptide sequence by introducing different structural modifications such as β-peptide bond and/or unusual side chains.[1] Also, many biologically active peptides incorporate hydroxy acids so that the synthesis of an ester instead of a peptide bond stands as a modification.[2] On the other hand adamantane is a well known pharmacophore present in different drugs.[3] Introducing cage molecules such as adamantane and homoadamantane into peptidomimetic structures should generate amphiphilic structures with enhanced possibility of permeation through biomembranes. In the scope of our investigation [4] we have prepared several α-amino and β-hydroxy esters or acids with homoadamantane (1a-1c) and adamantane (2a-2b) as the side chain. These molecules are convenient building blocks for introducing multiple interesting structural modifications in the new peptidomimetics

adamantane; homoadamantane; peptides; peptidomimetics

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