Stereocontrolled Synthesis of ψ[CH(CF3)NH]Gly-Peptides

Stereocontrolled Synthesis of ψ[CH(CF3)NH]Gly-Peptides

A novel class of peptidomimetics having a stereogenic [CH(CF3)NH] replacement for a [CONH] peptide bond has been synthesized. The new compounds have been obtained in a stereocontrolled fashion using a kinetically controlled aza-Michael addition of chiral α-amino acid esters to trans-3,3,3-trifluoro-...

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Veröffentlicht in:Organic letters 2003-10, Vol.5 (21), p.3887-3890
Hauptverfasser: Molteni, Marco, Volonterio, Alessandro, Zanda, Matteo
Format: Artikel
Sprache:eng
Schlagworte:
Models, Chemical
Molecular Mimicry
Molecular Structure
Oligopeptides - chemical synthesis
Oligopeptides - chemistry
Stereoisomerism
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Zusammenfassung:A novel class of peptidomimetics having a stereogenic [CH(CF3)NH] replacement for a [CONH] peptide bond has been synthesized. The new compounds have been obtained in a stereocontrolled fashion using a kinetically controlled aza-Michael addition of chiral α-amino acid esters to trans-3,3,3-trifluoro-1-nitropropene. The stereoselectivity is strongly influenced by the solvent, the base, its stoichiometry, and the R side-chain. Diastereomeric ratios higher than 11:1 were achieved using H-Val-OtBu·HCl in toluene with 1.1 equiv of DIPEA.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0354730