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-t...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 65; no. 25; pp. 8448 - 8453
Main Authors Pirrung, Michael C, James, Kenneth D, Rana, Vipul S
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.12.2000
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Chromatography, High Pressure Liquid
Histidine - chemistry
Kinetics
Magnetic Resonance Spectroscopy
Phosphorylation
Physical Sciences
Science & Technology
Spectrometry, Mass, Fast Atom Bombardment
Sulfhydryl Compounds - physiology
PHOSPHOHISTIDINE INTERMEDIATE
SIGNAL-TRANSDUCTION
PROTEIN
MECHANISM
PHOSPHOROTHIOATES
PHOSPHORYLATION
ESCHERICHIA-COLI
PHOSPHATE TRANSFER
NUCLEOSIDE DIPHOSPHATE KINASE
IDENTIFICATION
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Summary: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.
Bibliography:ark:/67375/TPS-LNK3G1MN-7
istex:7CE337553DE4453ED8A5D1FC151817F7C6A86DAB
Medline
NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo000771l