Application of substituted 2-(trimethylsilyl)ethyl esters to suppress diketopiperazine formation

Graphic The use of differently substituted 2-(trimethylsilyl)ethyl esters for C-terminal protection in peptide synthesis has been investigated. While the use of the unsubstituted 2-(trimethylsilyl)ethyl ester resulted in a substantial amount of diketopiperazine at the dipeptide stage, use of the cor...

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Bibliographic Details
Published inTetrahedron letters Vol. 45; no. 18; pp. 3585 - 3588
Main Authors Borsuk, Katarzyna, van Delft, Floris L, Eggen, Ivo F, ten Kortenaar, Paul B.W, Petersen, Annet, Rutjes, Floris P.J.T
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 26.04.2004
Subjects
Diketopiperazine formation
Protecting groups
Solution phase peptide synthesis
Protecting groups
Solution phase peptide synthesis
Diketopiperazine formation
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Summary:Graphic The use of differently substituted 2-(trimethylsilyl)ethyl esters for C-terminal protection in peptide synthesis has been investigated. While the use of the unsubstituted 2-(trimethylsilyl)ethyl ester resulted in a substantial amount of diketopiperazine at the dipeptide stage, use of the corresponding methyl-substituted silyl ester gave a significant reduction of this undesired pathway. Both esters could be deprotected by fluoride-induced cleavage under mild conditions.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2004.03.054