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.

Novel selenium-containing non-natural diamino acids

CAPUTO, ROMUALDO;CAPONE, STEFANIA;DELLA GRECA, MARINA;LONGOBARDO, LUIGI;PINTO G.
2007

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.
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Tetrahedron Letters 48 (2007) 1425–1427.pdf

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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11588/202339
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