Tris(2-carboxyethyl)phosphine Hydrochloride

Yost, Julianne M.; Knight, John D.; Coltart, Don M.

doi:10.1002/047084289x.rn00973

Cited by 4 publications

(5 citation statements)

References 57 publications

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“…This finding is in agreement with a previous result in which the reagent was found to be only poorly effective in releasing H 2 S from its Cu complex . When TCEP is added in excess, it can quickly react at acidic wine conditions and reduce disulfides and polysulfanes to free thiols, with the strength of the resulting phosphorus–oxygen bond (and possibly phosphorus–sulfur bond) making the reaction irreversible. ,− …”

Section: Results and Discussionsupporting

confidence: 92%

Copper(II)-Mediated Hydrogen Sulfide and Thiol Oxidation to Disulfides and Organic Polysulfanes and Their Reductive Cleavage in Wine: Mechanistic Elucidation and Potential Applications

Kreitman

Danilewicz²,

Jeffery

et al. 2017

J. Agric. Food Chem.

104

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Fermentation-derived volatile sulfur compounds (VSCs) are undesirable in wine and are often remediated in a process known as copper fining. In the present study, the addition of Cu(II) to model and real wine systems containing hydrogen sulfide (HS) and thiols provided evidence for the generation of disulfides (disulfanes) and organic polysulfanes. Cu(II) fining of a white wine spiked with glutathione, HS, and methanethiol (MeSH) resulted in the generation of MeSH-glutathione disulfide and trisulfane. In the present study, the mechanisms underlying the interaction of HS and thiols with Cu(II) is discussed, and a prospective diagnostic test for releasing volatile sulfur compounds from their nonvolatile forms in wine is investigated. This test utilized a combination of reducing agents, metal chelators, and low-oxygen conditions to promote the release of HS and MeSH, at levels above their reported sensory thresholds, from red and white wines that were otherwise free of sulfidic off-odors at the time of addition.

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Section: Results and Discussionsupporting

confidence: 92%

Copper(II)-Mediated Hydrogen Sulfide and Thiol Oxidation to Disulfides and Organic Polysulfanes and Their Reductive Cleavage in Wine: Mechanistic Elucidation and Potential Applications

Kreitman

Danilewicz²,

Jeffery

et al. 2017

J. Agric. Food Chem.

104

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Section: Methodsmentioning

confidence: 99%

“…These results indicated that we needed to include a reducing agent during apoHb sample preparation and the unfolding titration experiments. Dithiothreitol (DTT) was chosen because TCEP is unstable in phosphate buffers, 58 and at a concentration of 1 mM, DTT does not interfere with the far-UV CD signals. 59 Immediately after heme extraction into 2-butanone, all freshly isolated apoHb samples were dialyzed in 10 mM potassium phosphate buffer, 1 mM DTT buffer (pH 7) overnight at 4 °C.…”

Section: ■ Experimental Proceduresmentioning

confidence: 99%

Mechanism of Human Apohemoglobin Unfolding

Samuel

Phillips

et al. 2017

Biochemistry

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Removal of heme from human hemoglobin (Hb) results in formation of an apoglobin heterodimer. Titration of this apodimer with guanidine hydrochloride (GdnHCl) leads to biphasic unfolding curves indicating two distinct steps. Initially, the heme pocket unfolds and generates a dimeric intermediate in which ∼50% of the original helicity is lost, but the αβ interface is still intact. At higher GdnHCl concentrations, this intermediate dissociates into unfolded monomers. This structural interpretation was verified by comparing GdnHCl titrations for adult human hemoglobin A (HbA), recombinant fetal human hemoglobin (HbF), recombinant Hb cross-linked with a single glycine linker between the α chains, and recombinant Hbs with apolar heme pocket mutations that markedly stabilize native conformations in both subunits. The first phase of apoHb unfolding is independent of protein concentration, little affected by genetic cross-linking, but significantly shifted toward higher GdnHCl concentrations by the stabilizing distal pocket mutations. The second phase depends on protein concentration and is shifted to higher GdnHCl concentrations by genetic cross-linking. This model for apoHb unfolding allowed us to quantitate subtle differences in stability between apoHbA and apoHbF, which suggest that the β and γ heme pockets have similar stabilities, whereas the αγ interface is more resistant to dissociation than the αβ interface.

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“…Reduction by TCEP . An alternative to DTT for maintaining thiols in reduced state during NCL is TCEP, , which irreversibly reduces disulfides back to thiols once they are produced.…”

Section: Properties Of Cysteine or Selenocysteine Residuesmentioning

confidence: 99%

Native Chemical Ligation and Extended Methods: Mechanisms, Catalysis, Scope, and Limitations

et al. 2019

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The native chemical ligation reaction (NCL) involves reacting a C-terminal peptide thioester with an N-terminal cysteinyl peptide to produce a native peptide bond between the two fragments. This reaction has considerably extended the size of polypeptides and proteins that can be produced by total synthesis and has also numerous applications in bioconjugation, polymer synthesis, material science, and micro-and nanotechnology research. The aim of the present review is to provide a thorough mechanistic overview of NCL and extended methods. The most relevant properties of peptide thioesters, Cys peptides, and common solvents, reagents, additives, and catalysts used for these ligations are presented. Mechanisms, selectivity and reactivity are, whenever possible, discussed through the insights of computational and physical chemistry studies. The inherent limitations of NCL are discussed with insights from the mechanistic standpoint. This review also presents a palette of O,S-, N,S-, or N,Se-acyl shift systems as thioester or selenoester surrogates and discusses the special molecular features that govern reactivity in each case. Finally, the various thiol-based auxiliaries and thiol or selenol amino acid surrogates that have been developed so far are discussed with a special focus on the mechanism of long-range N,S-acyl migrations and selective dechalcogenation reactions.

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Tris(2-carboxyethyl)phosphine Hydrochloride

Cited by 4 publications

References 57 publications

Copper(II)-Mediated Hydrogen Sulfide and Thiol Oxidation to Disulfides and Organic Polysulfanes and Their Reductive Cleavage in Wine: Mechanistic Elucidation and Potential Applications

Copper(II)-Mediated Hydrogen Sulfide and Thiol Oxidation to Disulfides and Organic Polysulfanes and Their Reductive Cleavage in Wine: Mechanistic Elucidation and Potential Applications

Mechanism of Human Apohemoglobin Unfolding

Native Chemical Ligation and Extended Methods: Mechanisms, Catalysis, Scope, and Limitations

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