Elsevier

Tetrahedron Letters

Volume 48, Issue 8, 19 February 2007, Pages 1425-1427
Tetrahedron Letters

Novel selenium-containing non-natural diamino acids

https://doi.org/10.1016/j.tetlet.2006.12.096Get rights and content

Abstract

The general synthesis of a new class of non-natural diamino acids, 2-amino-3-[(2′-aminoalkyl)seleno]propanoic acids, or Se-(aminoalkyl)selenocysteines, is reported. Under the conditions devised, enantiopure N-Boc-protected β-l-iodoamines, which are readily generated from proteinogenic α-amino acids, were treated with the selenolate anion obtained from NaBH4 splitting of the Se–Se bond in commercial l-selenocystine. The Se-alkylation products were enantiomerically pure and the reaction is high yielding (92–98%), without any detectable traces of accompanying by-products.

References and notes (18)

  • A.L. Braga et al.

    Org. Lett.

    (2003)
  • A.L. Braga et al.

    Synlett

    (2005)
  • B.G. Davis

    Curr. Opin. Biotechnol.

    (2003)
  • E. Block et al.

    J. Agric. Food Chem.

    (2001)
  • R. Caputo et al.

    Tetrahedron

    (1995)
  • A.L. Braga et al.

    Eur. J. Org. Chem.

    (2005)
    A.L. Braga et al.

    J. Org. Chem.

    (2006)
  • Kyoto Encyclopedia of Genes and Genomes, KEGG, Release 40.0, October 2006....
  • G. Mugesh et al.

    Chem. Rev.

    (2001)
    C.W. Nogueira et al.

    Chem. Rev.

    (2004)
  • J.I. Rossato et al.

    Neurochem. Res.

    (2002)
There are more references available in the full text version of this article.

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Chiral aminoalkyl cation equivalents, 2.

Present address: Laboratorium für Organische Chemie, ETH Zürich, HCI Hönggerberg, Wolfgang-Pauli-Strasse 10, CH-8093 Zürich, Switzerland.

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