Triazole phosphohistidine analogues compatible with the Fmoc-strategy |
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Authors: | McAllister Tom E Webb Michael E |
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Institution: | Astbury Centre for Structural Molecular Biology and School of Chemistry, University of Leeds, Woodhouse Lane, Leeds, LS2 9JT, UK. |
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Abstract: | 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. |
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