Synthesis of a conformationally constrained delta-amino acid building block

O'Reilly, ElaineElaineO'ReillyPes, LaraLaraPesOrtin, YannickYannickOrtinMüller-Bunz, HelgeHelgeMüller-BunzParadisi, FrancescaFrancescaParadisi2013-03-202014-02-022013, Spri2013-02Amino Acidshttp://hdl.handle.net/10197/4196Conformationally restricted amino acids are important components in peptidomimetics and drug design. Herein, we describe the synthesis of a novel, non-proteinogenic constrained delta amino acid containing a cyclobutane ring, cis-3(aminomethyl)cyclobutane carboxylic acid (ACCA). The synthesis of the target amino acid was achieved in seven steps, with the key reaction being a base induced intramolecular nucleophilic substitution. A small library of dipeptides was prepared through the coupling of ACCA with proteinogenic amino acids.enThe final publication is available at www.springerlink.comNon-proteinogenic amino acidDipeptidesConformational restrictionCyclobutane ringSynthesis of a conformationally constrained delta-amino acid building blockJournal Article44251151810.1007/s00726-012-1362-32013-01-21https://creativecommons.org/licenses/by-nc-nd/3.0/ie/