(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 preparation on solid phase and under microwave dielectric heating of a highly lipidated peptide that can be considered as an acid stable analogue of the C-terminus of the H-Ras heptapeptides 180-186. © 2008 Elsevier Ltd. All rights reserved.

Cini, E., Lampariello, L.R., Rodriquez, M., Taddei, M. (2009). Synthesis and application in SPPS of a stable amino acid isostere of palmitoyl cysteine. TETRAHEDRON, 65(4), 844-848 [10.1016/j.tet.2008.11.033].

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

Cini, Elena
Supervision
;
Lampariello, Lucia Raffaella
Methodology
;
Rodriquez, Manuela
Methodology
;
Taddei, Maurizio
Conceptualization
2009-01-01

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 preparation on solid phase and under microwave dielectric heating of a highly lipidated peptide that can be considered as an acid stable analogue of the C-terminus of the H-Ras heptapeptides 180-186. © 2008 Elsevier Ltd. All rights reserved.
Cini, E., Lampariello, L.R., Rodriquez, M., Taddei, M. (2009). Synthesis and application in SPPS of a stable amino acid isostere of palmitoyl cysteine. TETRAHEDRON, 65(4), 844-848 [10.1016/j.tet.2008.11.033].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11365/1072750