Tetrahedron

Synthesis and application in SPPS of a stable amino acid isostere of palmitoyl cysteine

E Cini, LR Lampariello, M Rodriquez, M Taddei

Index: Cini, Elena; Lampariello, Lucia Raffaella; Rodriquez, Manuela; Taddei, Maurizio Tetrahedron, 2009 , vol. 65, # 4 p. 844 - 848

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Citation Number: 6

Abstract

(S)-2-Amino-4-(2-pentadecyl-1, 3-dioxolan-2-yl)-butanoic acid, 11, Pdiob, a synthetic analogue C-isostere of palmitoylated cysteine, has been prepared 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 for the ...