Organic Disulfides and Related Substances. IV. Thiolsulfonates and Disulfides Containing 2-Aminoethyl Moieties<sup>1</sup>

Field, Lamar; Owen, Terence C.; Crenshaw, R. R.; Bryan, Ann W.

doi:10.1021/ja01482a027

Cited by 36 publications

(19 citation statements)

References 1 publication

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“…A doubly positively charged thiosulfonate, 2-aminoethyl-2-aminoethanethiosulfonate, NH 3 + CH 2 CH 2 SO 2 SCH 2 CH 2 NH 3 + (AEAETS), adds the 2-aminoethylthio group to the Cys −SH, just like MTSEA. It was synthesized as previously described ( Field et al, 1961 , 1964 ). It was recrystallized by dissolving in methanol, adding about one-third volume of diethyl ether, and storing at 4°C for 2 d. By thin-layer chromatography on cellulose, developed in 60% ethanol/30% 0.1 N HCl/10% t-butanol, the product in methanol gave one ninhydrin-positive spot with an R f = 0.26.…”

Section: Methodsmentioning

confidence: 99%

State-dependent Accessibility and Electrostatic Potential in the Channel of the Acetylcholine Receptor

Pascual

Karlin

1998

The Journal of General Physiology

109

107

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Ion channel function depends on the chemical and physical properties and spatial arrangement of the residues that line the channel lumen and on the electrostatic potential within the lumen. We have used small, sulfhydryl-specific thiosulfonate reagents, both positively charged and neutral, to probe the environment within the acetylcholine (ACh) receptor channel. Rate constants were determined for their reactions with cysteines substituted for nine exposed residues in the second membrane-spanning segment (M2) of the α subunit. The largest rate constants, both in the presence and absence of ACh, were for the reactions with the cysteine substituted for αThr244, near the intracellular end of the channel. In the open state of the channel, but not in the closed state, the rate constants for the reactions of the charged reagents with several substituted cysteines depended on the transmembrane electrostatic potential, and the electrical distance of these cysteines increased from the extracellular to the intracellular end of M2. Even at zero transmembrane potential, the ratios of the rate constants for the reactions of three positively charged reagents with αT244C, αL251C, and αL258C to the rate constant for the reaction of an uncharged reagent were much greater in the open than in the closed state. This dependence of the rate constants on reagent charge is consistent with an intrinsic electrostatic potential in the channel that is considerably more negative in the open state than in the closed state. The effects of ACh on the rate constants for the reactions of substituted Cys along the length of αM2, on the dependence of the rate constants on the transmembrane potential, and on the intrinsic potential support a location of a gate more intracellular than αThr244.

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Section: Methodsmentioning

confidence: 99%

State-dependent Accessibility and Electrostatic Potential in the Channel of the Acetylcholine Receptor

Pascual

Karlin

1998

The Journal of General Physiology

109

107

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“…For this purpose, before preparing polystyryl-thiosulfonate resin, potassium thiotosylate was used as a matrix to react with electrophiles to produce toluene thiosulfonic esters: CH 3 C 6 H 4 SO 2 SK + R 1 X −→ CH 3 C 6 H 4 SO 2 SR 1 +KX (1) where, R 1 X represents electrophilic model compounds such as alkyl halides. The sulfur-sulfur bond in toluene thiosulfonic esters is able to be splitted by reducing agent to produce thiols (Kushko, 1971) or by thiols to produce disulfides (Parsons et al, 1965;Field et al, 1961Field et al, , 1965. In the former case, the thiols produced readily oxidized in the air to form mixed disulfides which would cause considerable complication in the subsequent analysis.…”

Section: Design and Preparation Of Potassium Polystyrylthiosulfonate mentioning

confidence: 99%

Thiolsulfonate functionalized polystyrene resin: Preparation and application in the isolation and identification of electrophilic mutagens

Carlson

2007

Journal of Environmental Sciences

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A new approach for isolation and identification of elecrtophilic mutagens from complex matrix was developed. Thiosulfonic anion was immobilized onto polystyrene beads and used as separation media. Potassium polystyryl-thiosulfonate, prepared from polystyrylsulfonyl chloride and KHS, was observed to selectively react with model electrophilic mutagens such as alkyl halides, α-chloroketones and α-chloroesters to produce polystyryl-thiosulfonic esters. After separation from other nonreactive organic compounds, the beads then reacted with ethanethiol to produce unsymmetrical ethyl disulfides which are easily detected by GC/MS. For one mutagenic compound, only one unsymmetrical disulfide was found to contain its structure part. Thus, the structure of the parent mutagens could be deduced from that of the unsymmetrical disulfides. The degree of functionalization of the potassium polystyryl-thiosulfonate resin was 1.11 mmol/g. Its reactivity was discussed and its recycling method was reported here.

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“…There were hints in the literature that supported the occurrence of a Pummerer reaction, as formulated in eq. 31. The reaction seems to be catalyzed by acid generated early in the thermolysis."…”

Section: Sulfoxidesmentioning

confidence: 99%

Forty-Five Years With a Hydra, Organosulfur Chemistry

Field

1993

Sulfur reports

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Organic Disulfides and Related Substances. IV. Thiolsulfonates and Disulfides Containing 2-Aminoethyl Moieties¹

Cited by 36 publications

References 1 publication

State-dependent Accessibility and Electrostatic Potential in the Channel of the Acetylcholine Receptor

State-dependent Accessibility and Electrostatic Potential in the Channel of the Acetylcholine Receptor

Thiolsulfonate functionalized polystyrene resin: Preparation and application in the isolation and identification of electrophilic mutagens

Forty-Five Years With a Hydra, Organosulfur Chemistry

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Organic Disulfides and Related Substances. IV. Thiolsulfonates and Disulfides Containing 2-Aminoethyl Moieties1

Cited by 36 publications

References 1 publication

State-dependent Accessibility and Electrostatic Potential in the Channel of the Acetylcholine Receptor

State-dependent Accessibility and Electrostatic Potential in the Channel of the Acetylcholine Receptor

Thiolsulfonate functionalized polystyrene resin: Preparation and application in the isolation and identification of electrophilic mutagens

Forty-Five Years With a Hydra, Organosulfur Chemistry

Contact Info

Product

Resources

About

Organic Disulfides and Related Substances. IV. Thiolsulfonates and Disulfides Containing 2-Aminoethyl Moieties¹