The Reaction of Thiol Compounds with Quinones

Snell, John M.; Weißberger, A.

doi:10.1021/ja01871a065

Cited by 111 publications

(44 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…An analogous internal cyclization reaction had been observed earlier when the corresponding product obtained by the action of thioglycollic acid on p-benzoquinone (21,22) was allowed to stand in a vacuum desiccator in the presence of phosphorus pentoxide (21).…”

supporting

confidence: 57%

Chemistry of the aminochromes. Part X. Some further observations on the reactions of aminochromes with thiols

Powell¹,

Heacock²,

Mattok³

et al. 1969

Can. J. Chem.

View full text Add to dashboard Cite

The reactions between aminochromes and thiols have been reinvestigated. In general aminochromes react with thiols to give mixtures of products including: 5,6-dihydroxyindoles; thio-substituted 5,6-dill>-droxyindoles (the mercapto residue is no\\ considered to be in the 4-position of the indole nucleus and not the 7-position as previously reported); and relatively unstable addition products formed between the aminochronie and the thiol. The mechanisms by which these conlpounds are formed are discussed. The characterization of three thio-substituted 5,6-dihydroxyindoles by nuclear magnetic resonance spectroscopy is described. The nuclear magnetic resonance spectra of a number of 5,6-diacetoxyindole derivat~vcs are reported.

show abstract

supporting

confidence: 57%

Chemistry of the aminochromes. Part X. Some further observations on the reactions of aminochromes with thiols

Powell¹,

Heacock²,

Mattok³

et al. 1969

Can. J. Chem.

View full text Add to dashboard Cite

show abstract

“…The reaction of benzoquinone with thiols has been previously described. [31] Reactions were carried out in 10 mm ammonium formate buffer at pH 2.8 and 6.7 with MT concentrations ranging between 20-40 mm. The neutral pH data set was collected at pH 6.7 and the low pH data set at pH 2.8.…”

Section: Modification Of Cysteines With Benzoquinone (Bq)mentioning

confidence: 99%

Metalation Kinetics of the Human α‐Metallothionein 1a Fragment Is Dependent on the Fluxional Structure of the apo‐Protein

Irvine

Duncan

Gullons

et al. 2014

Chemistry A European J

View full text Add to dashboard Cite

Mammalian metallothioneins are cysteine rich metal-binding proteins comprising, when fully metalated, two metal-binding domains: the α-domain binds with M4(II)S(Cys)11 stoichiometry and the β domain binds as M3(II)S(Cys)9 stoichiometry. While the fully metalated species have been widely studied, the metalation of the apoprotein is poorly understood. Key to a description of the metalation pathway(s) is the initial conformation of the apoprotein and the arrangement of the metal-coordinating cysteines prior to metalation. We report the effect of the ill-defined, globular structure of apoMT on metalation rates. In order to overcome the experimental limitations inherent in structural determinations of a fluxional protein we used a detailed analysis of the apo-α-metallothionein conformation based on the differential rate of cysteine modification with benzoquinone. The ESI mass spectral data show the presence of two distinct conformational families: one a folded conformational family at neutral pH and a second an unfolded family of conformations at low pH. The Cd(II) metalation properties of these two conformationally distinct families were studied using stopped-flow kinetics. Surprisingly, the unfolded apoprotein metalated significantly slower than the folded apoprotein, a result interpreted as being due to the longer time required to fold into the cluster structure when the fourth Cd(II) binds. These results provide the first evidence for the role of the structure of the apo-αMT in the metalation reaction pathways and show that cysteine modification coupled with ESI-MS can be used to probe structure in cysteine-rich proteins.

show abstract

“…10,11,28,29 In this study, from the reactions of p-chloranil with 2c, mixture of 2c with 3, 2d and 2e the compounds 4c, 10 7, 12 4d 10 and 4e 10 which have been published previously were respectively synthesized, but their spectroscopic properties weren't investigated intensely before. In addition, from the reactions of 1 with 2a-e and mixture of 2c with 3, in ethanol in the presence of Na2CO3, 4a-b, 5a-e, 6 and the reaction of 1 with 2a-e in methanol in the presence of Na 2 CO 3 , 4a-b and 8a-e were respectively synthesized.…”

Section: Resultsmentioning

confidence: 99%

The Synthesis of Novel Mono(alkoxy)-, Tris(thio)- and Tetrakis(thio)-Substituted Quinones from the Reactions of p-Chloranil with Various S-Nucleophiles

2009

Bulletin of the Korean Chemical Society

View full text Add to dashboard Cite

The tetrakis(thio)-substituted-1,4-benzoquinone products 4a-e, 6, 7, and the mono(alkoxy)-tris(thio)-substituted-1,4-benzoquinone products 5a-e and 8a-e were synthesized from the reactions of p-chloranil with some thiols and mixture of two different thiol compounds in alcohol in the presence of Na2CO3 at room temperature. The structures of the novel S,S,S,S-and S,S,S,O-substituted products, which were obtained by the reactions of p-chloranil as a starting compound with n-propanethiol, n-pentanethiol, n-decanethiol, n-dodecanethiol, 2-methyl-2-propanethiol, and mixture of n-decanethiol and n-cyclohexanethiol as S-nucleophiles, were characterized by spectroscopic methods.

show abstract

The Reaction of Thiol Compounds with Quinones

Cited by 111 publications

References 0 publications

Chemistry of the aminochromes. Part X. Some further observations on the reactions of aminochromes with thiols

Chemistry of the aminochromes. Part X. Some further observations on the reactions of aminochromes with thiols

Metalation Kinetics of the Human α‐Metallothionein 1a Fragment Is Dependent on the Fluxional Structure of the apo‐Protein

The Synthesis of Novel Mono(alkoxy)-, Tris(thio)- and Tetrakis(thio)-Substituted Quinones from the Reactions of p-Chloranil with Various S-Nucleophiles

Contact Info

Product

Resources

About