679011

Sigma-Aldrich

2-(Diphenylphosphino)terephthalic acid 1-methyl 4-pentafluorophenyl diester

97%

Synonym(s):
1-Methyl-4-(pentafluorophenyl)-2-(diphenylphosphino)-1,4-benzenedicarboxylate
Empirical Formula (Hill Notation):
C27H16F5O4P
Molecular Weight:
530.38
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

reaction suitability

reaction type: click chemistry

mp

109-111 °C

storage temp.

−20°C

SMILES string

COC(=O)c1ccc(cc1P(c2ccccc2)c3ccccc3)C(=O)Oc4c(F)c(F)c(F)c(F)c4F

InChI

1S/C27H16F5O4P/c1-35-27(34)18-13-12-15(26(33)36-25-23(31)21(29)20(28)22(30)24(25)32)14-19(18)37(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-14H,1H3

InChI key

OURNVXDJALDDIG-UHFFFAOYSA-N

Application

  • Staudinger ligation reagent for the conjugation of amine and azide containing compounds or biomolecules.
  • The amine functionalized molecule first reacts with the phosphine through the activated pentafluorophenyl ester.The azide-molecule is then reacted with the newly labeled phosphine to form the iminophosphorane, and the aza-ylide is subsequently captured by the methyl ester to yield the covalent conjugated product.
2-(Diphenylphosphino)terephthalic acid 1-methyl 4-pentafluorophenyl diester Staudinger Ligation Probe and Target
The Staudinger Ligation: A High-Yield, Chemoselective, and Mild Synthetic Method

Packaging

25 mg in amber glass bottle
100 mg in clear glass bottle

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
E Saxon et al.
Science (New York, N.Y.), 287(5460), 2007-2010 (2000-03-17)
Selective chemical reactions enacted within a cellular environment can be powerful tools for elucidating biological processes or engineering novel interactions. A chemical transformation that permits the selective formation of covalent adducts among richly functionalized biopolymers within a cellular context is...
Articles
Chemoselective ligation strategies are a key success factor for chemical biology research. Ligation techniques open pathways to fully synthetic large peptides and even proteins.
Read More
The reaction between an azide and a phosphine forming an aza-ylide was discovered almost a century ago by Nobel Prize laureate Herrmann Staudinger.
Read More

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