Stereoselective Synthesis of 3-Substituted 2-Aminocyclopentanecarboxylic Acid Derivatives and Their Incorporation into Short 12-Helical β-Peptides That Fold in Water

A stereoselective synthetic route is reported for the introduction of side chains at the 3-position of trans-2-aminocyclopentanecarboxylic acid (ACPC). Ring opening of the aziridine 2-benzyloxymethyl-6-azabicyclo[3.1.0]hexane with selected nucleophiles occurs in a regioselective manner and provides...

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Veröffentlicht in:	Journal of the American Chemical Society 2002-10, Vol.124 (42), p.12447-12452
Hauptverfasser:	Woll, Matthew G, Fisk, John D, LePlae, Paul R, Gellman, Samuel H
Format:	Artikel
Sprache:	eng
Schlagworte:	Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Chemistry Circular Dichroism Cyclohexanecarboxylic Acids - chemical synthesis Cyclohexanecarboxylic Acids - chemistry Cyclohexylamines - chemical synthesis Cyclohexylamines - chemistry Exact sciences and technology Nuclear Magnetic Resonance, Biomolecular Oligopeptides - chemical synthesis Oligopeptides - chemistry Organic chemistry Preparations and properties Protein Folding Protein Structure, Secondary Stereoisomerism
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