Alkylendischwefelchloride (IX. Mitteil. über organische Schwefelchloride)

Brintzinger, H.; Langheck, Malte; Ellwanger, Hans

doi:10.1002/cber.19540870305

Cited by 18 publications

(6 citation statements)

References 4 publications

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“…2,5-Dimethyl-3-(methyldithio)furan, 2-methyl-3-(methyldithio)furan, and 5-methylfurfuryl methyl disulfide were prepared by reacting the mercaptans with CH3SC1 (Brintzinger and Ellwanger, 1954). Some authentic samples of organic compounds were obtained from reliable commercial sources.…”

Section: Methodsmentioning

confidence: 99%

Investigation of sulfur-containing components in roasted coffee

Tressl¹,

Silwar²

1981

J. Agric. Food Chem.

110

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ACKNOWLEDGMENTWe are indebted to Dr. G. Borin, Centro di Studi sui Biopolymeri, CNR, Padova, for providing the synthetic acetylleucylleucylargininal (Leupeptin) and to Professor Galoppini, Istituto Industrie Agrarie, UniversitA di Pisa, for advice and assistance in preparing alfalfa juice. LITERATURE CITED Andrews, P. Biochem. J. 1965,95, 595. Bendal, M. R.; Cartwright, I. L.; Clark, P. I.; Lowe, G.; Nurse, D. Eur. J. Biochem. 1977, 79,201. Bittoni, A.; Sodini, G.; Emmi, E.; Cardinali, F. Riu. Ital. Sostanze Grasse 1977,54, 421. Camici, M.; Balestreri, E.; Tozzi, M. G.; Bacciola, D.; Saracchi, I.; Felicioli, R.; Ipata, P. L. Laskowski, M., Sr.; Kassel, B.; Peanasky, R. J.; Laskowski, M., Jr.In "Handbuch der physiologisch-und pathologisch-chemischen Analyse", 10th ed.; Lang, K.; Lenhartz, E., Eds.; SpringerBy means of distillation-extraction, adsorption chromatography, and capillary gas chromatography-mass spectrometry, 23 sulfur components (mercaptans, sulfides, and di-and trisulfides) were characterized in roasted coffee. Fifteen components were identified for the first time and confirmed by synthesis (among them are sulfur-containing furans and two dithiolanes). The amounts of sulfur components were determined in roasted Arabica and Robusta coffees, as well as in instant coffee.

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Section: Methodsmentioning

confidence: 99%

Investigation of sulfur-containing components in roasted coffee

Tressl¹,

Silwar²

1981

J. Agric. Food Chem.

110

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“…Ethar~esulfenyl chloride was prepared by the following procedure, based on the general method of Brintzinger et al (18). In an efficient fume hood ethyl disulfide (60 g, 0.4 mole) in a 1 1 flask protected with a calcium chloride tube, was cooled to -70' in a dry ice-acetone bath.…”

Section: Methodsmentioning

confidence: 99%

Reaction of ethanesulfenyl chloride with 2-methoxy-5,6-dihydro-2H-pyran

Baldwin¹,

Brown²

1969

Can. J. Chem.

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The reaction of ethanesulfenyl chloride with 2-methoxy-5,6-dihydro-2H-pyran gives only 413-chloro3a-ethylthio-213-methoxytetrahydropyran. A rationale is presented to explain the observed highly selective reaction.Canadian Journal of Chemistry, 47. 3553 (1969) Introduction Two recent reports from this laboratory (1,2) have described the reaction of alkane (or aralkane) sulfenyl chlorides with 3,4-dihydro-2H-pyran to produce trans-2-chloro-3-alkyl (or aralkyl) thiotetrahydropyran which, in the presence of sodium methoxide in methanol, gave trans-3-alkyl (or aralky1)-2-methoxytetrahydropyrans. A rationale was presented to explain the observed highly selective course of the reaction.The present communication describes the results obtained from the reaction of ethanesulfenyl chloride with 2-methoxy-5,6-dihydro-2H-pyran.

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“…n-Propyl 2-pyridyl disulphide This was first prepared by Dr. E. Ager from 2thiopyridone (Py-2-SH) and n-propanesulphenyl chloride (Brintzinger & Langhech, 1953, 1954 for use in another investigation (E. Ager, H. Suschitzky, T. Stuchbury & K. Brocklehurst, unpublished work). A saturated solution of Py-2-SH in methylene chloride was added dropwise to a stirred solution of n-propanesulphenyl chloride (prepared from 22.2g of n-propanethiol) in methylene chloride (300ml) until the orange colour disappeared.…”

Section: -Py-s-s-2-pymentioning

confidence: 99%

Characterization of the papain active centre by using two-protonic-state electrophiles as reactivity probes. Evidence for nucleophilic reactivity in the un-interrupted cysteine-25-histidine-159 interactive system

Shipton¹,

Brochlehurst²

1978

Biochemical Journal

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1.2,2'-Dipyridyl disulphide (2-Py-S-S-2-Py) and n-propyl 2-pyridyl disulphide (propyl-S-S-2-Py) were used as two-protonic-state reactivity probes to investigate the active centre of papain (EC 3.4.22.2).2. The existence of a striking rate optimum at pH approx. 4 in the reaction of papain not only with the symmetrical probe but also with the unsymmetrical probe is shown to constitute compelling evidence that the thiolate ion component of the cysteine-25-histidine-159 interactive system of papain possesses appreciable nucleophilic character. It is not a necessary requirement that the probe reagent should engage the imidazolium ion of histidine-159 in hydrogen-bonding for the sulphur atom of the interactive system to display nucleophilic character. The single proton-binding site of propyl-S-S-2-Py cannot simultaneously interrupt the active-centre ion pair and provide for rate enhancement as the pH is lowered towards 4. The possible implication of this for the mechanism of papain-catalysed hydrolysis is discussed. 3. The suspected difference in the active centres of papain and ficin (EC 3.4.22.3), which could be a lack in ficin of a carboxy group conformationally equivalent to that of aspartic acid-158 of papain is confirmed. The reactivity of the papain thiol group towards both probe reagents is controlled by two ionizations with pKa close to 4 that are positively co-operative. 4. In the reaction of papain with 2-Py-S-S-2-Py. the reactivity appears to be controlled also by an addition ionization with pKa approx. 5. Possible origins of this additional ionization are discussed. K. The spectral and ionization characteristics of propyl-S-S-2-Py are reported. 6. The reagent reacts rapidly with thiol groups at the sulphur atom distal from the pyridyl ring to provide, at pH values below 9, stoicheiometric release of 2-thiopyridone. This property, together with the ability of the reagent markedly to increase its electrophilicity consequent on protonation, suggests alkyl-2-pyridyl disulphides in general as valuable two-protonic-state reactivity probes with exceptional specificity for thiol groups.

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Alkylendischwefelchloride (IX. Mitteil. über organische Schwefelchloride)

Cited by 18 publications

References 4 publications

Investigation of sulfur-containing components in roasted coffee

Investigation of sulfur-containing components in roasted coffee

Reaction of ethanesulfenyl chloride with 2-methoxy-5,6-dihydro-2H-pyran

Characterization of the papain active centre by using two-protonic-state electrophiles as reactivity probes. Evidence for nucleophilic reactivity in the un-interrupted cysteine-25-histidine-159 interactive system

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