Dehydro-β-amino Acid Containing Peptides as Promising Sequences for Drug Development

In the course of a program devoted to the synthesis of small peptidic molecules mimicking the RGD (Arg‐Gly‐Asp) motif, the allylic amination of enantiomerically pure carbonates with 4‐substituted benzylamines afforded dehydro‐β‐amino esters through an SN2′ mechanism. The reaction performed with 4‐aminobenzylamine occurred with complete chemoselectivity, as the aliphatic amine was much more reactive than the aromatic one. This allowed useful precursors of biologically active compounds to be obtained, avoiding extra protection–deprotection steps. The same reaction performed on glycine‐derived amides gave similar results, allowing a novel type of RGD mimetic to be prepared, whose ability to inhibit cell adhesion was found to be very promising.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) The allylic amination of enantiomerically pure carbonates with 4‐substituted benzylamines afforded dehydro‐β‐amino esters and dehydro‐β‐amino amides derived from glycine by a SN2′ mechanism. The reaction performed with 4‐aminobenzylamine allowed useful precursors of RGD mimetics to be obtained, whose ability to inhibit cell adhesion was very promising.