Synthesis and Spectroscopic Characterization of β-Di-, β-Tri-, and β-Hexapeptides Built with (S)-2-Methylene-3-aminoalkanoic Acids Derived from Alanine, Valine, and Leucine

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Contents Vol 57(9)

doi:10.1071/CH04052

Synthesis and Spectroscopic Characterization of β-Di-, β-Tri-, and β-Hexapeptides Built with (S)-2-Methylene-3-aminoalkanoic Acids Derived from Alanine, Valine, and Leucine

Daniel J. Bierbaum ^A, Dieter Seebach ^A ^B

^A Laboratorium für Organische Chemie der Eidgenössischen Technischen Hochschule, ETH-Hönggerberg, HCI, 8093 Zürich, Switzerland.
^B Author to whom correspondence should be addressed (e-mail: seebach@org.chem.ethz.ch).





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Australian Journal of Chemistry 57(9) 859–863 http://dx.doi.org/10.1071/CH04052
Submitted: 27 February 2004 Accepted: 4 May 2004 Published online: 1 September 2004

Abstract

Methylthiomethylation and subsequent sulfoxidation and pyrolysis of the N-Boc-protected β³-amino acid methyl esters derived from Ala, Val, and Leu provided the α-methylene esters; these were then used to synthesize the β-peptides specified in the title (step-by-step and fragment coupling in solution). The novel β-peptides were fully characterized, but neither solid-state nor solution structures were found.