Synthesis of dithiols as reducing agents for disulfides in neutral aqueous solution and comparison of reduction potentials

Lamoureux, Guy; Whitesides, George M.

doi:10.1021/jo00055a015

Cited by 69 publications

(51 citation statements)

References 2 publications

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“…The disulfide bond can be cleaved by the thiol-disulfide exchange or the reduction using sodium borohydride, NaBH 4 . The thiol-disulfide exchange using dithiothreitol is commonly used to cleave the disulfide bond into free thiols 13) . We confirmed by the HPLC analysis that the disulfide bond was completely reduced by the addition of four times moles of dithiothreitol(DTT) in water at room temperature.…”

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Aqueous Solution Properties of Disulfide Linked Gemini and Cleaved Monomeric Thiol Surfactants

et al. 2008

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Monomeric thiol surfactants, [C n H 2n+1 N(CH 3 ) 2 CH 2 CH 2 SH]Br, were produced by the cleavage of gemini surfactant containing a disulfide bond in the spacer chain, [C n H 2n+1 N(CH 3 ) 2 CH 2 CH 2 SSCH 2 CH 2 N(CH 3 ) 2 C n H 2n+1 ]2Br. The disulfide bond was completely reduced by the addition of four times moles of dithiothreitol in water at room temperature. The critical micelle concentrations of monomeric surfactants were significantly increased in comparison with original gemini surfactants. The monomeric thiol surfactants were stable in the presence of dithiothreitol, whereas they returned gradually to their original gemini surfactants within several days due to air oxidation in water without dithiothreitol. The micelle formation induced by the disulfide linkage formation was suggested by the fluorescence intensity ratio of pyrene. The time course of decrease in thiol concentration associated with the recovery of gemini surfactants was confirmed by the absorption spectra utilizing the reactions with 4,4'-dithiopyridine.

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Aqueous Solution Properties of Disulfide Linked Gemini and Cleaved Monomeric Thiol Surfactants

et al. 2008

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“…Thiol-disulfi de exchange using DTT is commonly used to cleave the disulfi de bond into free thiols 8 . HPLC analysis showed that the disulfi de bond was reduced by the addition of DTT in water at room temperature.…”

Section: Resultsmentioning

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Aqueous Solution Properties of Disulfide-Linked Fluorinated Gemini and Cleaved Monomeric Thiol Surfactants

2011

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“…The most commonly used dithiol is DTT, which was introduced in 1964 by Cleland (4). The problem with thiols is that they work best at fairly high pH, because they react as thiol anions (29). High pHs should be avoided as this means increased risks for deamidation of the protein.…”

Section: Cleavage Of Cysteine Bridges-reviewing the Optionsmentioning

confidence: 99%

Sample Preparation for Peptide Mapping— A Pharmaceutical Quality-Control Perspective

Lundell

Schreitmüller

1999

Analytical Biochemistry

134

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Synthesis of dithiols as reducing agents for disulfides in neutral aqueous solution and comparison of reduction potentials

Cited by 69 publications

References 2 publications

Aqueous Solution Properties of Disulfide Linked Gemini and Cleaved Monomeric Thiol Surfactants

Aqueous Solution Properties of Disulfide Linked Gemini and Cleaved Monomeric Thiol Surfactants

Aqueous Solution Properties of Disulfide-Linked Fluorinated Gemini and Cleaved Monomeric Thiol Surfactants

Sample Preparation for Peptide Mapping— A Pharmaceutical Quality-Control Perspective

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