Tris (2-carboxyethyl) phosphine

Structural formula
General
Surname	Tris (2-carboxyethyl) phosphine
other names	TCEP; 3,3 ', 3' '- phosphanetriyl tripropanoic acid;
Molecular formula	C 9 H 15 O 6 P
External identifiers / databases
PubChem	119411
ChemSpider	106653
Wikidata	Q300902
properties
Molar mass	250.19 g mol −1 ; 286.65 g mol −1 (hydrochloride);
safety instructions
GHS labeling of hazardous substances Hydrochloride; danger
H and P phrases	H: 314
	P: 280-305 + 351 + 338-310
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tris (2-carboxyethyl) phosphine (TCEP) is a mild reducing agent from the group of phosphines . The compound also has a hydrochloride .

properties

Tris (2-carboxyethyl) phosphine is used in biochemistry for the selective reduction of disulfide bridges in cystine- containing proteins or to avoid oxidation of cysteines in proteins, e.g. B. before gel electrophoresis , chromatography or mass spectrometry . In contrast to the alternatively used mild reducing agents for disulfides such as β-mercaptoethanol , dithioerythritol or dithiothreitol , the reaction is irreversible because TCEP itself cannot form any disulfide bridges that would then react again with the cysteines. TCEP is also odorless, more water-soluble (therefore also not permeable to biomembrane ), less sensitive to oxidation with oxygen and reacts less with maleimides in the course of molecule labeling on cysteines. TCEP also reacts with maleimides under certain conditions. Since TCEP does not reduce nickel ions , it is used in metal chelate affinity chromatography .

In animal experiments, TCEP led to a reduction in the oxidation of sulfhydryls in the eye and to neuroprotective effects.

Individual evidence

↑ ^a ^b Data sheet Tris (2-carboxyethyl) phosphine hydrochloride, powder, ≥98% from Sigma-Aldrich , accessed on December 17, 2014 ( PDF ).
^ JR Winther, C. Thorpe: Quantification of thiols and disulfides. In: Biochimica et Biophysica Acta . Volume 1840, Number 2, February 2014, pp. 838-846. doi: 10.1016 / j.bbagen.2013.03.031 . PMID 23567800 . PMC 3766385 (free full text).
↑ External identifiers or database links for Tris (2-carboxyethyl) phosphine hydrochloride : CAS number: 51805-45-9, EC number: 629-759-1, ECHA InfoCard: 100.157.950 , PubChem : 2734570 , ChemSpider : 2016318 , Wikidata : Q27279627 .
↑ Ruegg, UT and Rudinger, J .: Reductive cleavage of cystine disulfides with tributylphosphine . In: Methods Enzymol. . 47, 1977, pp. 111-116. doi : 10.1016 / 0076-6879 (77) 47012-5 . PMID 927167 .
↑ A. Fischer, M. Montal: Molecular dissection of botulinum neurotoxin reveals interdomain chaperone function. In: Toxicon . Volume 75, December 2013, pp. 101-107. doi: 10.1016 / j.toxicon.2013.01.007 . PMID 23396042 . PMC 3797153 (free full text).
↑ Interchim: TCEP technical information (product data sheet ).
↑ Shafer, DE; Inman, JK; Lees, A .: Reaction of Tris (2-carboxyethyl) phosphine (TCEP) with Maleimide and α-Haloacyl Groups: Anomalous Elution of TCEP by Gel Filtration . In: Anal Biochem . . 282, No. 1, 2000, pp. 161-164. doi : 10.1006 / abio.2000.4609 . PMID 10860517 .
↑ Tyagarajan K, Pretzer E, Wiktorowicz JE: Thiol-reactive dyes for fluorescence labeling of proteomic samples . In: Electrophoresis . 24, No. 14, 2003, pp. 2348-2358. doi : 10.1002 / elps.200305478 . PMID 12874870 .
^ V. Bergendahl, LC Anthony, T. Heyduk, RR Burgess: On-column tris (2-carboxyethyl) phosphine reduction and IC5-maleimide labeling during purification of a RpoC fragment on a nickel-nitrilotriacetic acid column. In: Analytical Biochemistry . Volume 307, Number 2, August 2002, pp. 368-374. PMID 12202256 .
^ CJ Lieven, LA Levin: Tools for studying early events in optic neuropathies. In: Eye. Volume 21 Suppl 1, December 2007, pp. S21-S24. doi: 10.1038 / sj.eye.6702883 . PMID 18157175 .

[Sigma-1] Data sheet Tris (2-carboxyethyl) phosphine hydrochloride, powder, ≥98% from Sigma-Aldrich , accessed on December 17, 2014 ( PDF ).

[2] JR Winther, C. Thorpe: Quantification of thiols and disulfides. In: Biochimica et Biophysica Acta . Volume 1840, Number 2, February 2014, pp. 838-846. doi: 10.1016 / j.bbagen.2013.03.031 . PMID 23567800 . PMC 3766385 (free full text).

[3] External identifiers or database links for Tris (2-carboxyethyl) phosphine hydrochloride : CAS number: 51805-45-9, EC number: 629-759-1, ECHA InfoCard: 100.157.950 , PubChem : 2734570 , ChemSpider : 2016318 , Wikidata : Q27279627 .

[4] Ruegg, UT and Rudinger, J .: Reductive cleavage of cystine disulfides with tributylphosphine . In: Methods Enzymol. . 47, 1977, pp. 111-116. doi : 10.1016 / 0076-6879 (77) 47012-5 . PMID 927167 .

[5] A. Fischer, M. Montal: Molecular dissection of botulinum neurotoxin reveals interdomain chaperone function. In: Toxicon . Volume 75, December 2013, pp. 101-107. doi: 10.1016 / j.toxicon.2013.01.007 . PMID 23396042 . PMC 3797153 (free full text).

[FT-242214-6] Interchim: TCEP technical information (product data sheet ).

[7] Shafer, DE; Inman, JK; Lees, A .: Reaction of Tris (2-carboxyethyl) phosphine (TCEP) with Maleimide and α-Haloacyl Groups: Anomalous Elution of TCEP by Gel Filtration . In: Anal Biochem . . 282, No. 1, 2000, pp. 161-164. doi : 10.1006 / abio.2000.4609 . PMID 10860517 .

[8] Tyagarajan K, Pretzer E, Wiktorowicz JE: Thiol-reactive dyes for fluorescence labeling of proteomic samples . In: Electrophoresis . 24, No. 14, 2003, pp. 2348-2358. doi : 10.1002 / elps.200305478 . PMID 12874870 .

[9] V. Bergendahl, LC Anthony, T. Heyduk, RR Burgess: On-column tris (2-carboxyethyl) phosphine reduction and IC5-maleimide labeling during purification of a RpoC fragment on a nickel-nitrilotriacetic acid column. In: Analytical Biochemistry . Volume 307, Number 2, August 2002, pp. 368-374. PMID 12202256 .

[PMID18157175-10] CJ Lieven, LA Levin: Tools for studying early events in optic neuropathies. In: Eye. Volume 21 Suppl 1, December 2007, pp. S21-S24. doi: 10.1038 / sj.eye.6702883 . PMID 18157175 .