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TCEP

Tris(2-carboxyethyl)phosphine (TCEP) is a water-soluble, odorless tertiary phosphine compound that serves as a potent reducing agent in biochemistry and molecular biology, primarily for the selective cleavage of disulfide bonds into thiols without affecting other functional groups.^[1] Introduced in 1991 as an alternative to thiol-based reductants like dithiothreitol (DTT), TCEP offers superior stability in aqueous solutions and at low pH values, enabling its use in a wide range of experimental conditions.^[1]^[2] Chemically, TCEP has the formula C₉H₁₅O₆P and a molecular weight of 250.19 g/mol, existing typically as the hydrochloride salt (TCEP·HCl) with enhanced solubility up to 310 g/L in water.^[2]^[3] It operates through a phosphine-mediated mechanism that reduces disulfides rapidly at room temperature while remaining inert toward metals and other reductants, making it thiol-free and less prone to oxidation.^[1]^[4] This stability allows TCEP to maintain reducing activity over extended periods, unlike DTT, which oxidizes more readily.^[5] In practice, TCEP is indispensable for protein refolding, peptide synthesis, and enzymatic assays, where it prevents unwanted disulfide bridging and is compatible with downstream techniques such as mass spectrometry and chromatography due to its non-interfering byproducts.^[6]^[4] It also finds applications in reducing sulfoxides, N-oxides, and azides in organic synthesis, highlighting its versatility beyond biological contexts.^[7]

Properties

Chemical structure

Tris(2-carboxyethyl)phosphine (TCEP) is a tertiary phosphine compound characterized by its molecular formula \ce{C9H15O6P}.^[2] The molecule features a central phosphorus atom bonded to three identical 2-carboxyethyl substituents, represented by the structural formula \ce{(HO2CCH2CH2)3P}.^[2] This symmetric arrangement centers around the trivalent phosphorus, with each arm consisting of a two-carbon alkyl chain terminating in a carboxylic acid group, conferring polarity and distinguishing TCEP from non-functionalized alkylphosphines.^[1] As a trialkylphosphine derivative, TCEP incorporates carboxylic acid moieties that impart water solubility, a key attribute absent in hydrophobic phosphines like triphenylphosphine.^[1] The identical substituents ensure the molecule is achiral, with no stereocenters or optical activity, as the phosphorus lacks asymmetry due to its pyramidal geometry and equivalent ligands.^[2] In practice, TCEP is most often utilized as its hydrochloride salt, denoted TCEP·HCl, with the molecular formula \ce{C9H16ClO6P}.^[8] This protonated form enhances stability, forming an odorless, crystalline, air-stable solid that remains soluble in aqueous media.^[1]

Physical properties

Tris(2-carboxyethyl)phosphine (TCEP) is typically handled and supplied as its hydrochloride salt (TCEP·HCl), which appears as a white to off-white crystalline powder.^[8] The molecular weight of the free base TCEP is 250.19 g/mol, while the hydrochloride salt has a molecular weight of 286.65 g/mol.^[2]^[8] The melting point of TCEP·HCl is approximately 176–178 °C.^[9]^[10] TCEP·HCl is odorless, a property that facilitates safe laboratory handling compared to thiol-based reductants.^[5] Density and other bulk properties of TCEP·HCl are not extensively characterized in the literature, though it is consistently described as a solid at room temperature with a reported bulk density around 1.04 g/mL.^[10]^[11]

Stability and solubility

TCEP hydrochloride demonstrates exceptional water solubility, exceeding 310 g/L at 20°C, owing to its highly hydrophilic character conferred by the three carboxylic acid groups in its structure.^[12]^[3] This property facilitates its direct dissolution in aqueous buffers across a broad pH range without the need for organic cosolvents.^[3] In terms of stability, TCEP exhibits strong resistance to aerial oxidation at neutral pH, showing less than 20% oxidation after 3 weeks in non-phosphate buffers, markedly superior to dithiothreitol (DTT), which has a half-life of approximately 10 hours at pH 7.5.^[3]^[13] Its stability spans pH 2 to 10, showing no significant degradation after 24 hours in solutions ranging from 100 mM HCl to 100 mM NaOH, though oxidation accelerates in phosphate buffers near neutral pH; optimal reducing performance occurs at pH 7–8.^[3] For storage, the solid hydrochloride salt is recommended at -20°C in a desiccated environment for long-term stability up to two years, while aqueous solutions remain viable for weeks at 4°C.^[14]^[3] Regarding solubility in non-aqueous media, TCEP displays poor compatibility with non-polar solvents and only limited dissolution in polar protic ones, such as approximately 2 mg/mL in dimethylformamide (DMF) and 3.3 mg/mL in dimethyl sulfoxide (DMSO).^[15] This restricted solubility in organic solvents underscores its preference for aqueous environments in practical applications.^[3]

Synthesis

Hydrolysis of tris(2-cyanoethyl)phosphine

The primary laboratory method for synthesizing tris(2-carboxyethyl)phosphine (TCEP) involves the acid hydrolysis of the precursor tris(2-cyanoethyl)phosphine, denoted as (NC-CH₂-CH₂)₃P. This compound is commercially available and undergoes hydrolysis of its three nitrile groups to form the corresponding carboxylic acids under acidic conditions. The method, first detailed in seminal work on phosphine reducing agents, provides a straightforward route to TCEP hydrochloride on a laboratory scale.^[1] The reaction proceeds by refluxing tris(2-cyanoethyl)phosphine in 6 M aqueous HCl, typically for 4-6 hours under an inert atmosphere such as argon to minimize oxidation. The concentrated acid facilitates the hydrolysis, converting each -CN group to -COOH while forming the trihydrochloride salt. A simplified representation of the transformation is given by the equation:

(\ce{NC-CH2-CH2})_3\ce{P} + 6 \ce{H2O} + 3 \ce{HCl} \rightarrow (\ce{HOOC-CH2-CH2})_3\ce{P \cdot 3HCl}

This process yields the product efficiently, with reported recoveries of 70-90% after purification.^[1] Following hydrolysis, the reaction mixture is cooled to 0 °C, prompting precipitation of the TCEP hydrochloride as a white solid. The precipitate is collected by filtration and purified via recrystallization from a water-ethanol mixture to afford analytically pure material. This purification step ensures removal of any unreacted precursor or byproducts, enhancing the compound's utility as a reducing agent.^[1]

Other synthetic routes

An alternative synthetic route to TCEP involves the Michael addition of tetrakis(hydroxymethyl)phosphonium chloride to alkyl acrylates, followed by acid hydrolysis of the resulting triester intermediate. This method avoids the use of highly toxic phosphine gas (PH₃), which is employed in the conventional synthesis from acrylonitrile, by starting with the safer phosphonium salt precursor. In a detailed procedure outlined in a Chinese patent, tetrakis(hydroxymethyl)phosphonium chloride (80% aqueous solution) is reacted with ethyl acrylate in an organic solvent such as ethanol or tetrahydrofuran, in the presence of a base like sodium hydroxide or potassium hydroxide, at 30–60°C for 4–7 hours to form tris(2-ethoxycarbonylethyl)phosphonium chloride (compound II).^[16] Subsequent hydrolysis of this ester intermediate with concentrated hydrochloric acid (12 mol/L) at 80–90°C for 3–5 hours yields TCEP hydrochloride, which is purified by recrystallization from distilled water to obtain a white crystalline product with high purity.^[16] This ester-based route represents a variant of the Michael addition strategy, utilizing acrylic acid derivatives (e.g., ethyl acrylate) under basic conditions to build the carbon-phosphorus framework, contrasting with the nitrile pathway in the standard method. The approach enhances safety and product purity through controlled hydrolysis conditions and simple post-reaction purification, achieving yields suitable for laboratory-scale production.^[16] However, compared to the direct hydrolysis of tris(2-cyanoethyl)phosphine, this method introduces additional steps involving ester formation and saponification, potentially leading to lower overall yields due to the multi-stage process and sensitivity to hydrolysis conditions. Scalability remains a challenge, as the use of phosphonium salts and specific solvents may complicate large-scale operations without optimized equipment for base-catalyzed additions.^[16]

Reactions

Disulfide reduction

TCEP functions as a potent reductant for disulfide bonds, converting symmetrical disulfides (R-S-S-R) into two equivalent thiol groups (2 R-SH) while undergoing oxidation to its corresponding phosphine oxide byproduct, (HO_2CCH_2CH_2)_3P=O. This reaction proceeds stoichiometrically, with one equivalent of TCEP typically sufficient per disulfide bond, though excess is often employed to ensure complete conversion and account for any competing oxidation. The reduction is conducted in aqueous solutions, where TCEP concentrations of 1-10 mM are standard, at room temperature (approximately 20-25°C), and under mildly neutral to slightly acidic conditions (pH 6-8) to optimize stability and reactivity. These parameters allow for straightforward implementation in laboratory settings, with the broad pH tolerance of TCEP (extending from 4 to 9) providing flexibility for diverse substrates without significant loss of efficacy. A key advantage of TCEP lies in its selectivity, as it targets disulfides while sparing other functional groups, such as aldehydes, particularly at neutral pH where side reactions are minimized. While highly selective for free disulfides, TCEP can also reduce metal-coordinated sulfurs in some metalloproteins. This specificity arises from the phosphine's preference for nucleophilic attack on the electrophilic sulfur atoms in disulfides, avoiding interference with carbonyl reductions that might occur with less selective agents.^[17] In terms of efficiency, TCEP achieves near-complete reduction of small-molecule disulfides within minutes under standard conditions, demonstrating its high reactivity.^[17] For protein disulfides, which are often buried within folded structures, the process extends to several hours, influenced by accessibility and the number of bonds present, yet remains faster and more reliable than many thiol-based reductants.^[18] The resulting phosphine oxide byproduct is highly water-soluble, non-toxic, and biologically inert, allowing it to remain in reaction mixtures without necessitating removal for downstream applications.

Reaction mechanism

The reduction of disulfides by TCEP proceeds via a nucleophilic substitution mechanism at the sulfur-sulfur bond. The lone pair on the phosphorus atom of TCEP acts as a nucleophile, attacking one of the sulfur atoms in the disulfide (R'S-SR'), leading to the formation of a phosphonium intermediate (TCEP⁺-SR') and the displacement of a thiolate anion (⁻SR'). This step involves a two-electron transfer, cleaving the S-S bond in an SN2-like fashion, where the rate-determining step is the initial nucleophilic attack.^[1] The phosphonium intermediate then undergoes rapid hydrolysis in aqueous solution. Water attacks the phosphorus center, resulting in the formation of the oxidized TCEP species, TCEP oxide (a phosphine oxide), and the release of the second thiol (RSH) along with hydroxide. The overall stoichiometry is one equivalent of TCEP per disulfide bond reduced, yielding TCEP oxide and two equivalents of thiol, with the oxide product being inert and unable to participate in further reduction cycles.^[1] The reaction exhibits second-order kinetics, first-order with respect to both TCEP and the disulfide. The nucleophilicity of TCEP is influenced by pH due to the protonation state of its three carboxylic acid groups; deprotonation at higher pH enhances reactivity by increasing the availability of the phosphorus lone pair, with optimal conditions around pH 6-8.^[1] The overall mechanism can be represented as:

\text{TCEP} + \text{R'S-SR'} \rightarrow [\text{TCEP}^+-\text{SR'} \cdot {^-}\text{SR'}] \rightarrow \text{TCEP=O} + 2 \text{R'SH}

where the bracketed species denotes the ion pair intermediate prior to hydrolysis.

Side reactions

In applications involving mass spectrometry, TCEP can induce unintended peptide backbone cleavage at cysteine residues under mild conditions, such as incubation with 1–10 mM TCEP at 37 °C for 24 hours or 2 mM at 4 °C for 2 weeks. This side reaction fractures the cysteine, generating heterogeneous products through peptide bond hydrolysis and C–C bond cleavage, with maximum efficiency observed at pH 8 across a range of 2.2–10.0.^[19] Over-reduction is rare but can occur with metal-bound thiols in proteins or other biomolecules, where TCEP releases sulfhydryl groups from metal-sulfur coordination, potentially disrupting targeted disulfide reduction in metalloproteins. This effect arises from TCEP's ability to distinguish and liberate metal-bound cysteine ligands, as seen in redox state analyses of metallothioneins.^[20] TCEP is resistant to air oxidation in most aqueous buffers, with less than 20% oxidation after 3 weeks across pH 1.5–11.1. However, in phosphate-buffered saline (PBS), oxidation accelerates at neutral pH, fully oxidizing at 0.35 M pH 7 within 72 hours and 50% at 0.15 M pH 8, but remains minimal at pH >10.5 or <6.0. The pKa of approximately 7.7 relates to TCEP's ionization, influencing reactivity but not directly oxidation rates.^[1]^[3] Impure TCEP from incomplete hydrolysis of tris(2-cyanoethyl)phosphine may contain trace cyanide, which can interfere with sensitive assays by forming complexes or inhibiting enzymes, though commercial preparations are typically purified to minimize this. To mitigate these side reactions, fresh TCEP solutions should be prepared immediately before use, avoiding neutral phosphate buffers where complete oxidation occurs within 72 hours at 0.35 M and pH 7. Stability exceeds 3 weeks (with <20% oxidation) in most non-phosphate buffers across pH 1.5–11.1; prolonged exposure to pH extremes or air should be limited, and lower concentrations or shorter incubation times are recommended for mass spectrometry preparations.^[3]

Applications

General chemical applications

TCEP functions as a versatile reducing agent in organic synthesis, particularly for the selective cleavage of disulfide bonds in small organic molecules. This property makes it valuable for deprotecting thiol groups in synthetic intermediates, such as those used in the preparation of peptide precursors or other sulfur-containing compounds, where precise control over reduction is essential. Unlike traditional thiol-based reductants, TCEP operates effectively in aqueous environments at mildly acidic pH, enabling the quantitative reduction of strained or unstrained disulfides without requiring organic solvents or harsh conditions. For instance, it rapidly converts symmetric and mixed disulfides to their corresponding thiols in water, facilitating downstream reactions like alkylation or conjugation.^[1] TCEP is also employed in organic synthesis for the reduction of sulfoxides to sulfides, sulfonyl chlorides to thiols, N-oxides to amines, and azides to amines, offering mild conditions and high selectivity in aqueous or mixed solvent systems.^[7] In analytical chemistry, TCEP is utilized for the accurate quantitation of iodine and iodate species through stoichiometric reduction. It quantitatively reduces iodate (IO₃⁻) to iodide (I⁻) in acidic media, allowing the total iodine content to be determined via subsequent ceric-arsenite titration or other iodide-specific assays, with detection limits as low as 0.25 nmol per assay (approximately 0.5 μM).^[21] This method offers high specificity and avoids interference from common oxidants, making it suitable for environmental and pharmaceutical analyses. Additionally, TCEP's stability in solution ensures reproducible results without the need for immediate use after preparation. Within material science, TCEP plays a key role in polymer synthesis and surface modification by generating free thiols from disulfide precursors, thereby stabilizing reactive thiol groups against oxidation during processing. It is commonly applied in thiol-ene click reactions to functionalize glycidyl-bearing polymers or keratin-based materials, where reduction of disulfides enables efficient conjugation of sulfhydryl molecules for enhanced material properties like biocompatibility or adhesion. For example, controlled TCEP-mediated reduction on wool fibers introduces thiol termini for subsequent step-growth polymerization, improving dyeability and mechanical strength without compromising fiber integrity.^[22] A primary advantage of TCEP over dithiothreitol (DTT) and β-mercaptoethanol (BME) in these chemical applications is its odorless nature and lack of thiol byproducts, preventing contamination in odor-sensitive syntheses or purifications. TCEP also exhibits superior air stability and resistance to oxidation, remaining effective at concentrations up to 1 M in aqueous buffers for extended periods, whereas DTT and BME degrade rapidly under similar conditions. This stability, coupled with its irreversible reduction mechanism, minimizes side reactions and simplifies reaction workups in organic and polymer chemistries.^[23]

Applications in biology and medicine

TCEP serves as a key reducing agent in biological research for denaturing proteins by cleaving disulfide bonds during sample preparation for sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE), where it is typically added to loading buffers at final concentrations of 5-50 mM to ensure complete reduction without the odor or instability issues of alternatives like dithiothreitol (DTT).^[3] This application is particularly valuable for maintaining protein unfolding under denaturing conditions, allowing accurate assessment of molecular weights.^[24] In mass spectrometry workflows, TCEP is employed as a pre-treatment reagent for intact protein analysis at concentrations of 5-10 mM, offering advantages over DTT by avoiding thiol-related artifacts and ion suppression due to its non-thiol nature and compatibility with downstream labeling or ionization processes.^[25] Its stability in aqueous buffers further supports its use in proteomic sample preparation without requiring removal prior to analysis.^[24] For enzyme studies, TCEP maintains the reduced state of critical cysteine residues in proteins such as caspases and phosphatases, enabling accurate evaluation of their catalytic activity and redox regulation; for instance, it is added at 1-5 mM during assays of cysteine proteases like caspases to prevent disulfide reformation that could inhibit function.^[26] Similarly, in phosphatase research, low concentrations (around 2 mM) preserve thiol groups in the active site, facilitating studies of oxidative inactivation and reactivation mechanisms.^[27] In nucleic acid research, TCEP deprotects thiolated oligonucleotides by reducing disulfide linkages, commonly using a 10 mM solution for 1 hour at room temperature to generate free thiols for conjugation or immobilization applications in DNA and RNA studies.^[28] Medically, TCEP plays a role in the development of disulfide-linked antibody-drug conjugates (ADCs) for targeted drug delivery, where it facilitates selective reduction of interchain disulfides at 3-5 mM to attach cytotoxic payloads while preserving antibody stability, as seen in processes yielding homogeneous therapeutics with enhanced therapeutic indices.^[29] It is also emerging in redox biology as a component in probes for detecting cysteine oxidation states, aiding investigations into oxidative stress and signaling pathways at millimolar levels in cellular assays.^[30] Specific protocols often incorporate TCEP at 1-50 mM in lysis or refolding buffers for biological applications, such as solubilizing proteins from cell extracts or promoting correct disulfide formation during recombinant protein refolding, leveraging its broad pH tolerance and resistance to oxidation.^[31]

History

Initial discovery

Tris(2-carboxyethyl)phosphine (TCEP) was first synthesized and reported in 1969 by researchers M. E. Levison, A. S. Josephson, and D. M. Kirschenbaum, affiliated with Pierce Chemical Company in Rockford, Illinois.^[32] The compound was developed as a water-soluble and odorless trialkylphosphine intended for general biochemical applications, addressing limitations of existing phosphines that were often insoluble or malodorous.^[32] This innovation aimed to provide a more practical reducing agent for handling biological materials in aqueous environments. The initial publication appeared in the journal Experientia, where TCEP was described as a phosphine analog suitable for analytical chemistry techniques involving reductions of biological substances, such as gamma-globulin (IgG).^[32] In these early experiments, TCEP effectively reduced disulfide bonds in proteins at concentrations lower than those required for traditional agents like 2-mercaptoethanol, yielding comparable polypeptide products and demonstrating its efficacy in inactivating rheumatoid factor via latex agglutination assays.^[32] However, its recognition at the time focused on broad reductive potential rather than specific applications to disulfide cleavage. The first synthesis of TCEP was accomplished through the hydrolysis of tris(2-cyanoethyl)phosphine under refluxing aqueous conditions, resulting in a stable, water-soluble product that expanded the utility of phosphines in basic biochemical chemistry. Early studies emphasized its structural novelty as a carboxylated trialkylphosphine, but applications remained confined to fundamental reductions without extensive exploration of specialized uses.^[32]

Development and commercialization

In the late 1980s, TCEP gained recognition as a reducing reagent for disulfide bonds in proteins, surpassing dithiothreitol (DTT) in stability and lack of odor, which facilitated its breakthrough in biochemical applications.^[33] A pivotal 1991 study detailed its selective reduction of disulfides without affecting other residues, establishing TCEP as a preferred alternative to thiol-based reductants like DTT for protein denaturation and modification.^[1] Commercialization began in the early 1990s when Pierce Chemical Company (now Thermo Fisher Scientific) launched TCEP·HCl as a high-purity, premium reagent optimized for laboratory use in protein chemistry.^[34] This introduction aligned with advancements in scalable synthesis via acid hydrolysis of tris(2-cyanoethyl)phosphine, enabling efficient production while maintaining TCEP's water solubility and reactivity.^[1] TCEP's adoption accelerated during the biotech expansion of the 1990s and 2000s, driven by its resistance to oxidation, compatibility with a broad pH range, and simplicity in handling compared to volatile or odorous alternatives.^[35] Today, it is widely supplied by major vendors including Sigma-Aldrich and Cayman Chemical, supporting routine protocols in proteomics and molecular biology.^[36]^[37] For pharmaceutical-scale applications, GMP-grade TCEP·HCl is manufactured via validated hydrolysis processes, as offered by producers like BioVectra to meet regulatory standards for bioconjugation and antibody-drug conjugate preparation.^[38] By the 2000s, TCEP had become a standard tool in global laboratories, reflected in thousands of citations for its foundational literature, with no significant innovations in its formulation or production reported after 2020.^[1]

References

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TCEP is a tertiary phosphine in which phosphane is substituted with three 2-carboxyethyl groups. It is a commonly used reducing agent.
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TCEP (Tris(2-carboxyethyl)phosphine) is a reducing agent that maintains high activity at low pH. It is a component of the AccuMAP® Low pH Protein Digestion Kit.
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Molecular Formula. C9H16ClO6P. Synonyms. 51805-45-9; Tris(2-carboxyethyl)phosphine hydrochloride; TCEP Hydrochloride; TCEP HCl; Tcep hydrochloride [MI]. View ...
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cGMP TRIS(2-CARBOXYETHYL) PHOSPHINE, HYDROCHLORIDE. (cGMP TCEP-HCl). Catalogue Number. 1301. CAS Registry Number. 51805-45-9. Molecular Formula. C9H15O6P-HCl.