The 2-(diphenylphosphino) ethyl group (DPPE) as a new carboxyl-protecting group in peptide chemistry

The use of the 2-(diphenylphosphino)ethyl group for carboxyl-protection of amino acids or peptides is described. This group is easily introduced by esterification using 2-(diphenylphosphino) ethanol in the presence of dicyclohexylcarbodiimide and 4-(dimethylamino)pyridine. These Dppe esters are stab...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Tetrahedron 1984, Vol.40 (16), p.3087-3094
Hauptverfasser:	Chantreux, Dominique, Gamet, Jean-Paul, Jacquier, Robert, Verducci, Jean
Format:	Artikel
Sprache:	eng
Schlagworte:	2-(diphenylphosphino)-ethanol 2-(diphenylphosphino)ethyl group carboxyl group protection carboxyl-protection Chemistry esterification Exact sciences and technology Organic chemistry Peptide synthesis Peptides Preparations and properties β-elimination
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

Beschreibung
Zusammenfassung:	The use of the 2-(diphenylphosphino)ethyl group for carboxyl-protection of amino acids or peptides is described. This group is easily introduced by esterification using 2-(diphenylphosphino) ethanol in the presence of dicyclohexylcarbodiimide and 4-(dimethylamino)pyridine. These Dppe esters are stable under the standard conditions for peptide synthesis. Deprotection is carried out under mild conditions by quaternisation using methyl iodide followed by a β-elimination induced by fluoride ion or potassium carbonate.
ISSN:	0040-4020 1464-5416
DOI:	10.1016/S0040-4020(01)82433-9