(S)-2-Amino-4-(2-pentadecyl-1,3-dioxolan-2-yl)-butanoic acid (Pdiob), a synthetic analog C-isostere of palmitoylated cysteine, has been prepd. starting from tetrabenzyl glutamic acid. The less hindered benzyl carboxylate ester was transformed into the corresponding β-ketophosphonate and subjected to a Horner-Wadsworth-Emmons reaction followed by hydrogenation/hydrogenolysis. This product was used in solid-phase peptide synthesis under microwave dielec. heating for a highly lipidated peptide that can be considered as an acid stable analog of the C-terminus of the H-Ras heptapeptides 180-186.
Synthesis and application in SPPS of a stable amino acid isoster of palmitoyl cysteine
RODRIQUEZ, Manuela;
2009
Abstract
(S)-2-Amino-4-(2-pentadecyl-1,3-dioxolan-2-yl)-butanoic acid (Pdiob), a synthetic analog C-isostere of palmitoylated cysteine, has been prepd. starting from tetrabenzyl glutamic acid. The less hindered benzyl carboxylate ester was transformed into the corresponding β-ketophosphonate and subjected to a Horner-Wadsworth-Emmons reaction followed by hydrogenation/hydrogenolysis. This product was used in solid-phase peptide synthesis under microwave dielec. heating for a highly lipidated peptide that can be considered as an acid stable analog of the C-terminus of the H-Ras heptapeptides 180-186.File in questo prodotto:
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