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; Dieter Seebach

doi:10.1071/CH04052

RESEARCH ARTICLE

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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

+ Author Affiliations

- Author Affiliations

^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).

Australian Journal of Chemistry 57(9) 859-863 https://doi.org/10.1071/CH04052
Submitted: 27 February 2004 Accepted: 4 May 2004 Published: 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.

Acknowledgments

We gratefully acknowledge financial support from Novartis Pharma AG (Basel). We thank Professor B. Jaun for the NMR measurements and for all his attempts to find an NMR solution structure of 6. The results described herein are part of the Ph.D. thesis of D.J.B. (ETH-Zürich, Dissertation No. 15509, 2004).

References

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

Abstract

Acknowledgments

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