Synthesis of a conformationally constrained delta-amino acid building block

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Title: Synthesis of a conformationally constrained delta-amino acid building block
Authors: O'Reilly, Elaine
Pes, Lara
Ortin, Yannick
Müller-Bunz, Helge
Paradisi, Francesca
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Date: Feb-2013
Online since: 2014-02-02T04:00:14Z
Abstract: Conformationally 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.
Type of material: Journal Article
Publisher: Springer
Journal: Amino Acids
Volume: 44
Issue: 2
Start page: 511
End page: 518
Copyright (published version): 2013, Springer
Keywords: Non-proteinogenic amino acidDipeptidesConformational restrictionCyclobutane ring
DOI: 10.1007/s00726-012-1362-3
Language: en
Status of Item: Not peer reviewed
Appears in Collections:Chemistry Research Collection

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