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914746

Sigma-Aldrich

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:
21300-59-4
Molecular Weight:
189.00
UNSPSC Code:
12352200

Quality Level

100

Assay

≥95%

form

liquid

storage temp.

−20°C

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.

Other Notes

Bioinspired Thiophosphorodichloridate Reagents for Chemoselective Histidine Bioconjugation

Storage Class Code

10 - Combustible liquids

Flash Point(F)

175.8 °F

Flash Point(C)

79.9 °C

Certificates of Analysis (COA)

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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

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