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Triazole phosphohistidine analogues compatible with the Fmoc-strategy.

McAllister, TE and Webb, ME (2012) Triazole phosphohistidine analogues compatible with the Fmoc-strategy. Organic and Biomolecular Chemistry, 10 (20). 4043 - 4049 . ISSN 1477-0520


Phosphorylation of histidine is essential for bacterial two-component signalling; its importance to modulation of eukaryotic protein function remains undefined. Until recently, no immunochemical probes of this post-translational modification existed, however triazole phosphonate analogues of this modified amino acid have now been applied to the generation of site-specific antibodies. The protecting group strategy used in the original report is incompatible with standard protocols for Fmoc-solid phase peptide synthesis. In this paper, we report the application of P(III) chemistry to generate the complementary dibenzyl and di-tert-butyl phosphonate esters. These forms of the triazole analogue are fully compatible with standard Fmoc-SPPS and are therefore ideal for wider application by the chemical and biochemical community.

Item Type: Article
Keywords: Histidine, Isomerism, Molecular Structure, Peptides, Triazoles
Institution: The University of Leeds
Academic Units: The University of Leeds > Faculty of Maths and Physical Sciences (Leeds) > School of Chemistry (Leeds)
Depositing User: Symplectic Publications
Date Deposited: 22 Aug 2012 10:05
Last Modified: 08 Feb 2013 17:39
Published Version: http://dx.doi.org/10.1039/c2ob25517k
Status: Published
Publisher: Royal Society of Chemistry
Identification Number: 10.1039/c2ob25517k
URI: http://eprints.whiterose.ac.uk/id/eprint/74467

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