title: Stable triazolylphosphonate analogues of phosphohistidine.
abstract: Histidine-phosphorylated proteins and the corresponding kinases are important components of bacterial and eukaryotic cell-signalling pathways, and are therefore potential drug targets. The study of these biomolecules has been hampered by the lability of the phosphoramidate functional group in the phosphohistidines and the lack of generic antibodies. Herein, the design and concise synthesis of stable triazolylphosphonate analogues of N1- and N3-phosphohistidine, and derivatives suitable for bioconjugation, are described.
authors: School of Biomedical, Biomolecular and Chemical Sciences, The University of Western Australia, Crawley, WA 6009, Australia.
authors: Shin
authors: S
authors: Mukai
authors: Gavin R
authors: GR
authors: Flematti
authors: Lindsay T
authors: LT
authors: Byrne
authors: Paul G
authors: PG
authors: Besant
authors: Paul V
authors: PV
authors: Attwood
authors: Matthew J
authors: MJ
authors: Piggott
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D057930:Click Chemistry; D003300:Copper / Q000737:chemistry; D005449:Fluorenes / Q000138:chemical synthesis; D006241:Haptens / Q000737:chemistry; D006639:Histidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification
chemical_list: D000596:Amino Acids; D005449:Fluorenes; D006241:Haptens; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D063065:Organophosphonates; D014230:Triazoles; D006639:Histidine; D003300:Copper; D000409:Alanine; C005436:phosphohistidine