The 2-(diphenylphosphino) ethyl group (DPPE) as a new carboxyl-protecting group in peptide chemistry |
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| Authors: | Dominique Chantreux Jean-Paul Gamet Robert Jacquier Jean Verducci |
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| Institution: | Equipe de Recherche Associée au C.N.R.S. No 169, place E. Bataillon 34060 Montpellier Cedex - France |
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| Abstract: | 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. |
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| Keywords: | Peptide synthesis carboxyl-protection 2-(diphenylphosphino)ethyl group esterification β-elimination |
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