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Issue 31, 2016
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Bis(arylmethyl)-substituted unsymmetrical phosphites for the synthesis of lipidated peptides via Staudinger-phosphite reactions

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Abstract

With this study we introduce new unsymmetrical phosphites to obtain lipidated peptide-conjugates starting from easily accessible azide-modified amino acid or peptide precursors. For this purpose, we investigated which substituents at alkyl phosphites lead to the highest formation of mono-alkylated phosphoramidate peptides. We found that phosphites containing one alkyl-chain and two picolyl or benzyl-substituents delivered alkyl phosphoramidate-conjugates in high yields, which also allowed a chemoselective lipidation of an unprotected azido polypeptide. Finally, monolipidated phosphoramidate peptides obtained by the unsymmetrical Staudinger phosphite reaction led to the formation of micelle-like structures and cellular uptake.

Graphical abstract: Bis(arylmethyl)-substituted unsymmetrical phosphites for the synthesis of lipidated peptides via Staudinger-phosphite reactions

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Supplementary files

Article information


Submitted
19 Apr 2016
Accepted
11 Jul 2016
First published
11 Jul 2016

Org. Biomol. Chem., 2016,14, 7500-7508
Article type
Paper

Bis(arylmethyl)-substituted unsymmetrical phosphites for the synthesis of lipidated peptides via Staudinger-phosphite reactions

N. Nischan, M.-A. Kasper, T. Mathew and C. P. R. Hackenberger, Org. Biomol. Chem., 2016, 14, 7500
DOI: 10.1039/C6OB00843G

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