A convenient solid phase synthesis of S-palmitoyl transmembrane peptides

Rijkers, D.T.S., Kruijtzer, J.A.W., Killian, J.A. and Liskamp, R.M.J. (2005) A convenient solid phase synthesis of S-palmitoyl transmembrane peptides. Tetrahedron Letters, 46(19), pp. 3341-3345. (doi:10.1016/j.tetlet.2005.03.079)

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Abstract

S-Palmitoylated peptides are important tools as models for integral membrane proteins to study peptide–lipid interactions. Herein, we report a convenient solid phase synthesis of S-palmitoyl transmembrane peptides. The highly acid labile S-(4-methoxytrityl) group is preferred over the S-(tert-butylsulfanyl) group for protection of the cysteine side chain since the latter gives rise to quantitative desulfurization during on-resin deprotection. The resulting free thiol function is modified with palmitic acid via a carbodiimide-mediated coupling and the title compounds are obtained in good yields and purity.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Liskamp, Professor Robert
Authors: Rijkers, D.T.S., Kruijtzer, J.A.W., Killian, J.A., and Liskamp, R.M.J.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Tetrahedron Letters
ISSN:0040-4039
ISSN (Online):1873-3581

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