914746
Thiophosphoro alkyne dichloridate
≥95%
Synonym(s):
O-(Prop-2-yn-1-yl) phosphorodichloridothioate, Chemoselective histidine labeling reagent, Phosphorodichloridothioate 2-propyn-1-ol, Propargyl thiophosphorodichloridate, TPAC, Thiophosphoro alkyne dichloridate, Thiophosphorodichloridate reagent, Thiophosphorus electrophile
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About This Item
Empirical Formula (Hill Notation):
C3H3Cl2OPS
CAS Number:
Molecular Weight:
189.00
MDL number:
UNSPSC Code:
12352106
NACRES:
NA.22
Quality Level
assay
≥95%
form
liquid
storage temp.
−20°C
SMILES string
[P](=S)(Cl)(Cl)OCC#C
InChI
1S/C3H3Cl2OPS/c1-2-3-6-7(4,5)8/h1H,3H2
InChI key
HPJLQEFYLAALCL-UHFFFAOYSA-N
Application
Thiophosphoro alkyne dichloridate (TPAC) is a histidine labeling reagent developed by the Chang lab that mimics native post-translational His phosphorylation. The alkyne allows for subsequent reactions or addition of payloads by copper-assisted alkyne-azide cycloaddition (CuAAC) chemistry. TPAC was also demonstrated to covalently modify His-tags, and by clicking on polyarginine tags, enabled protein delivery into live cells.
Storage Class
10 - Combustible liquids
flash_point_f
175.8 °F
flash_point_c
79.9 °C
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Shang Jia et al.
Journal of the American Chemical Society, 141(18), 7294-7301 (2019-04-25)
Site-selective bioconjugation to native protein residues is a powerful tool for protein functionalization, with cysteine and lysine side chains being the most common points for attachment owing to their high nucleophilicity. We now report a strategy for histidine modification using
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 914746-100MG | 04061842093748 |