6-Methyl-5,8-quinoline Quinone

Christiansen, W.G.; Dolliver, M. A.

doi:10.1021/ja01850a501

Cited by 6 publications

(5 citation statements)

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“…No resonances for disulfide 126 was observed in the 107-108 ppm region. Thus, under these reaction conditions, and in agreement with the report of Modena and Todesco,28 the disulfide 126 is not produced in detectable (<5%) amounts during the course of the oxidation of 127 Peroxidation of thiosulfinate 129 under similar conditions for the oxidation of 127 gave 128,130,131, and presumably 64.12 ******This result clearly demonstrates that the oxidation of 129 (or 127) cannot occur exclusively at the sulfinyl sulfur atom. Thus, oxidation of 127 or 129 at the sulfenyl sulfur atom could involve w'c-disulfoxides 132 or 134, respectively.…”

supporting

confidence: 91%

“…2. Symmetrical S-Aryl Arenesulflnothioates The oxidation of 127 by peroxyethanoic acid at -20 °C in trichloromethane showed that the resonances at 8 101.30 and 103.19 ppm, due to the fluorines of 127, decreased in intensity with time with the concurrent appearance of resonances at 8 96.97 and 101.05 ppm for 128. No resonances for disulfide 126 was observed in the 107-108 ppm region.…”

mentioning

confidence: 99%

“…tained,19,23,25,[127][128][129] subsequent studies showed the alleged dioxides (187 and 191) to have the respective thiosulfonate structures(188 and 192) 32,126,[130][131]. …”

mentioning

confidence: 99%

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vic-Disulfoxides and OS-sulfenyl sulfinates

Freeman¹

1984

Chem. Rev.

113

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supporting

confidence: 91%

mentioning

confidence: 99%

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vic-Disulfoxides and OS-sulfenyl sulfinates

Freeman¹

1984

Chem. Rev.

113

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“…54)."' Since our product was 128 quite different from three reported earlier to be 128, the structure was confirmed with special care (NMR, Rarnan, UV, and mass spectra; molecular weight). '42 Formation at the sulfide sulfur of a sulfoxide and a sulfonium salt showed selective reaction of a sulfide to be possible in the presence of a di~ulfide.…”

Section: Seven-and Eight-membered Ringssupporting

confidence: 47%

Forty-Five Years With a Hydra, Organosulfur Chemistry

Field

1993

Sulfur reports

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“…The same product was obtained by oxidation of cystamine dihydrochloride with aq. H202 by the method of Christiansen & Dolliver (1941). These authors refer to the product incorrectly as a disulphoxide.…”

Section: -Aminoethyl 2'-aminoethanethiolsulphonate Dihydrochloridementioning

confidence: 99%

A reporter group delivery system with both absolute and selective specificity for thiol groups and an improved fluorescent probe containing the 7-nitrobenzo-2-oxa-1,3-diazole moiety

Stuchbury¹,

Shipton²,

Norris³

et al. 1975

Biochemical Journal

205

130

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1. 4-(N-2-Aminoethyl2'-pyridyl disulphide)-7-nitrobenzo-2-oxa-1,3-diazole (compound I) was synthesized and evaluated as a fluorescent labelling reagent for thiol groups. 2. The design of compound (I) as one example of a general type of reporter group delivery reagent (2-pyridyl-S-S-X, where X contains an environmentally sensitive spectroscopic probe) is discussed. 3. The electronic absorption spectrum of compound (I) was determined over a wide range of pH and the spectral changes that accompany its reaction with low-molecular-weight thiols, e.g. L-cysteine, and with papain (EC 3.4.22.2) and bovine serum albumin are discussed. 4. A new value of epsilon343 for 2-thiopyridone (Py-2-SH) was determined as 8.08 X 10(3) +/- 0.08 X 10(3)M-1-cm-1. 5. Spectral analysis of the reactions of compound (I) with L-cysteine and with papain (in the pH range 3.5-8.0) showed that even under equimolar conditions the reaction (thiol-disulphide interchange to release Py-2-SH) is essentially stoicheimoetric and probably proceeds by specific attack at the sulphur atom distal from the pyridyl ring of compound (I). 6. The fluorescence-emission spectra of compound (I) and of the products of its reaction with papain and with ficin (EC 3.4.22.3) were determined. Compound (I) is highly fluorescent in aqueous solution. Excitation within the intense visible absorption band (lambda max. 481 nm, epsilon max. 2.52 X 10(4)M-1-cm-1) provides green fluorescence with an emission maximum at 540 nm. Both papain and ficin labelled by reaction with compound (I) are characterized by fluorescence-emission maxima (535 nm and 530 nm respectively) of even higher intensity. The fluorescence emission of the product of the reaction of papain with compound (I) was shown to be 25 times more intense than that of the product of the reaction of papain with 4-chloro-7-nitrobenzo-2-oxa-1,3-diazole (Nbd chloride). 7. The second-order rate constants (k2) for the reactions of compound (I) and of Nbd chloride with GSH, papain, albumin, ficin, 2-benzimidazolylmethanethiol and 2-benzimidazolylethanethiol were determined at 25.0 degrees C and various pH values. At pH4 the values of k2(compound I)/k2(Nbd chloride) are: GSH, 288; albumin, 36; papain 3 X 10(3); ficin, 3 X 10(4). 8. The pH-k2 profiles for the reactions of compound (I) and of Nbd chloride with the two 2-benzimidazolylalkanethiols were determined. Of the four profiles only that for the reaction of compound (I) with 2-benzimidazolylmethanethiol is characterized by a striking rate maximum in acidic media.

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6-Methyl-5,8-quinoline Quinone

Cited by 6 publications

References 0 publications

vic-Disulfoxides and OS-sulfenyl sulfinates

vic-Disulfoxides and OS-sulfenyl sulfinates

Forty-Five Years With a Hydra, Organosulfur Chemistry

A reporter group delivery system with both absolute and selective specificity for thiol groups and an improved fluorescent probe containing the 7-nitrobenzo-2-oxa-1,3-diazole moiety

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