Skip to Content
Merck
All Photos(1)

Documents

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C3H3Cl2OPS
CAS Number:
21300-59-4
Molecular Weight:
189.00
UNSPSC Code:
12352106
NACRES:
NA.22

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service