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Australian Journal of Chemistry
  An international journal for chemical science
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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 and 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).


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.

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





   
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