title: 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.
authors.affiliation: School of Chemistry, University of Leeds, Leeds, UK.
authors.forename: Tom E
authors.initials: TE
authors.lastname: McAllister
authors.forename: Michael G
authors.initials: MG
authors.lastname: Nix
authors.forename: Michael E
authors.initials: ME
authors.lastname: Webb
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry; D000595:Amino Acid Sequence; D005449:Fluorenes / Q000737:chemistry*; D006639:Histidine / Q000031:analogs & derivatives* / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry; D010766:Phosphorylation
chemical_list: D005449:Fluorenes; D010455:Peptides; C557745:fluorenylmethoxycarbonyl-4-diethylphosphonotriazolylalanine; D006639:Histidine; D000409:Alanine; C005436:phosphohistidine