Design, synthesis, conformational analysis and application of indolizidin-2-one dipeptide mimics

• Published in: Organic & biomolecular chemistry 2014-07, Vol.12 (28), p.552-57
• Main Authors: Khashper, Arkady, Lubell, William D
• Format: Article
• Language: English
• Subjects: Amino Acids - chemical synthesis; Amino Acids - chemistry; Antithrombins - chemical synthesis; Antithrombins - chemistry; Dinoprost - antagonists & inhibitors; Dinoprost - chemistry; Dipeptides - chemical synthesis; Dipeptides - chemistry; Humans; Indolizines - chemical synthesis; Indolizines - chemistry; Intracellular Signaling Peptides and Proteins - antagonists & inhibitors; Intracellular Signaling Peptides and Proteins - chemistry; Mitochondrial Proteins - antagonists & inhibitors; Mitochondrial Proteins - chemistry; Molecular Conformation; Molecular Mimicry; Receptors, Cell Surface - antagonists & inhibitors; Receptors, Cell Surface - chemistry; STAT3 Transcription Factor - antagonists & inhibitors; STAT3 Transcription Factor - chemistry; Stereoisomerism
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/c4ob00777h

Growth in the field of peptide mimicry over the past few decades has resulted in the synthesis of many new compounds and the investigation of novel pharmacological agents. Azabicyclo[X.Y.0]alkanone amino acids are among the attractive classes of constrained mimics, because they can create rigid peptide structures for probing the conformation and roles of natural motifs in recognition events important for biological activity. Herein, we review the last ten years of the synthesis, conformational analysis and activity of analogs of the azabicyclo[4.3.0]alkan-2-one amino acid subclass, so-called indolizidin-2-one amino acids, with particular attention on their employment as inputs for biological applications. Growth in the field of peptide mimicry over the past few decades has resulted in the synthesis of many new compounds and the investigation of novel pharmacological agents.