9085. TCEP

Nomenclature

CAS number: 5961-85-3
3,3′,3″-Phosphinidynetrispropanoic acid; tris(2-carboxyethyl)phosphine.
C9H15O6P; mol wt 250.19.
C 43.21%, H 6.04%, O 38.37%, P 12.38%.

Description and references

Disulfide reducing agent. Prepn: M. M. Rauhut et al., J. Am. Chem. Soc. 81, 1103 (1959); and mechanism: J. A. Burns et al., J. Org. Chem. 56, 2648 (1991). Use as a reducing agent in measurement of redox activity: M. Neuburger et al., Eur. J. Biochem. 267, 2882 (2000); in determn of aminothiols: J. Krijt et al., Clin. Chem. 47, 1821 (2001); in protein sequencing: T.-Y. Yen et al., J. Mass Spectrom. 37, 15 (2002); B. P. English et al., J. Am. Chem. Soc. 124, 4995 (2002).

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 51805-45-9

Properties

Odorless, air-stable, white crystalline solid. mp 176°. uv max: 192, 218 nm (ε 150, 180 L mol1 cm1). Water soluble. pKa 7.66. When pH of dilute solutions is less than pKa, air oxidation occurs slowly.

Use

Biochemical tool for selective reduction of disulfide bridges at low pH; reductant for redox assays.