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Synlett 1997; 1997(SI): 437-438
DOI: 10.1055/s-1997-6117
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Synthesis of a β-Hexapeptide from (R)-2-Aminomethyl-alkanoic Acids and Structural Investigations

Tobias Hintermann, Dieter Seebach*
  • *Laboratorium für Organische Chemie der Eidgenössischen Technischen Hochschule ETH Zürich, CH-8092 Zürich, Switzerland, Fax +41-1-632 1144; e-Mail: <Seebach@org.chem.ethz.ch>
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Publikationsdatum:
31. Dezember 2000 (online)

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The (R) α-branched β-amino acid derivatives 3-5 with the side chains of alanine, valine and leucine are prepared by amino-methylation of acyloxazolidinones 2a-c and are used for the synthesis of the trifluoroacetate salt 9 of H(-β2-HVal-β2-HAla-β2-HLeu)2-OH. The CD spectrum of compound 9 is compared with that of the isomer H(-β3-HVal-β3-HAla-β3-HLeu)2-OH (1) built from the corresponding β-branched β-amino acids.

α-branched β-amino acids - diastereoselective synthesis - β-peptides - CD-spectroscopy - 31 helix