Three-Dimensional Structural Diversity-Oriented Peptidomimetics Based on the Cyclopropylic Strain

Conformationally restricted peptidomimetics comprising eight stereoisomeric scaffolds with three-dimensional structural diversity were designed based on the structural features of cyclopropane, that is, cyclopropylic strain, which mimic wide-ranging tetrapeptide conformations covering β-turns throug...

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Veröffentlicht in:	Organic letters 2013-04, Vol.15 (7), p.1686-1689
Hauptverfasser:	Mizuno, Akira, Miura, Shiho, Watanabe, Mizuki, Ito, Yoshihiko, Yamada, Shizuo, Odagami, Takenao, Kogami, Yuji, Arisawa, Mitsuhiro, Shuto, Satoshi
Format:	Artikel
Sprache:	eng
Schlagworte:	Amino Acid Sequence Cyclopropanes - chemical synthesis Cyclopropanes - chemistry Cyclopropanes - pharmacology Humans Models, Molecular Oligopeptides - chemical synthesis Oligopeptides - chemistry Oligopeptides - pharmacology Peptidomimetics - chemical synthesis Peptidomimetics - chemistry Peptidomimetics - pharmacology Protein Structure, Secondary Receptor, Melanocortin, Type 4 - metabolism Stereoisomerism
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Zusammenfassung:	Conformationally restricted peptidomimetics comprising eight stereoisomeric scaffolds with three-dimensional structural diversity were designed based on the structural features of cyclopropane, that is, cyclopropylic strain, which mimic wide-ranging tetrapeptide conformations covering β-turns through β-strands. Stereoselective synthesis of the designed peptidomimetics led to the identification of nonpeptidic melanocortin-4 receptor ligands.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol400469w