Thiophosphorylation of histidine.
The preparation of a novel phosphorus species, thiophosphoramidate, has enabled the specific thiophosphorylation of histidine at its 3-position. The rates of phosphorylation and thiophosphorylation of histidine are reported, as well as the spectroscopic properties of both thiophosphoramidate and 3-thiophosphohistidine. Structural assignment of the latter was made by analogy to the NMR properties of the known 3-phosphohistidine. The alkylation of 3-thiophosphohistidine by phenacyl bromide serves as a model for the introduction of labeling or probe reagents into histidine phosphorothioate-containing proteins.
Pirrung
M C
MC
Department of Chemistry, Levine Science Research Center, Duke University, Durham, North Carolina 27708-0317, USA. pirrung@chem.duke.edu
James
K D
KD
Rana
V S
VS
D002851:Chromatography, High Pressure Liquid; D006639:Histidine / Q000737:chemistry*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D010766:Phosphorylation; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013438:Sulfhydryl Compounds / Q000502:physiology*
D013438:Sulfhydryl Compounds; D006639:Histidine