Issue 4, 2011

Fmoc-chemistry of a stable phosphohistidine analogue

Abstract

We report the synthesis of the phosphohistidine analogue, Fmoc-4-diethylphosphonotriazolylalanine 5 and its incorporation into peptides. Our synthesis of 5 has enabled us to demonstrate that the analogue is compatible with Fmoc-solid phase peptide synthesis (SPPS) conditions. Standard cleavage conditions yield the diethyl phosphonate-protected peptide, however this can be subsequently deprotected using trimethylsilyl bromide to yield the free phosphonic acid-containing peptides.

Graphical abstract: Fmoc-chemistry of a stable phosphohistidine analogue

Supplementary files

Article information

Article type
Communication
Submitted
05 Oct 2010
Accepted
27 Oct 2010
First published
22 Nov 2010

Chem. Commun., 2011,47, 1297-1299

Fmoc-chemistry of a stable phosphohistidine analogue

T. E. McAllister, M. G. Nix and M. E. Webb, Chem. Commun., 2011, 47, 1297 DOI: 10.1039/C0CC04238B

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements