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Dehydro‐β‐amino Acid Containing Peptides as Promising Sequences for Drug Development
Author(s) -
Cardillo Giuliana,
Gennari Arianna,
Gentilucci Luca,
Mosconi Elisa,
Tolomelli Alessandra,
Troisi Stefano
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900870
Subject(s) - chemistry , chemoselectivity , amination , reductive amination , amino acid , amine gas treating , allylic rearrangement , glycine , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry , catalysis
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 S N 2′ 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)