29945-69-5Relevant academic research and scientific papers
Photochemical metal-free aerobic oxidation of thiols to disulfides
Spiliopoulou, Nikoleta,Kokotos, Christoforos G.
supporting information, p. 546 - 551 (2021/01/28)
Thiol oxidation to disulfides is an area of great importance in organic synthesis, both for synthetic and biological purposes. Herein, we report a mild, inexpensive and green photochemical approach for the synthesis of both symmetrical and non-symmetrical disulfides, using metal-free and environmentally friendly conditions. Utilizing phenylglyoxylic acid as the photoinitiator, common household bulbs as the light source and a simple inorganic salt as the additive, a versatile oxidation of thiols leading to products in excellent yields is described. This journal is
Construction of disulfide bonds in peptides via immobilized platinum(IV) complex oxidation
Sun, Jingjing,Zhang, Yamei,Huo, Shuying,Shen, Shigang
supporting information, (2019/12/24)
A novel TentaGel resin supported platinum(IV) complex named TentaGel-Pt(IV) was synthesized and characterized by SEM, XPS, ICP-MS and UV–vis spectrophotometry. The formation of intramolecular disulfides in eleven dithiol-containing peptides of variable lengths using TentaGel-Pt(IV) was investigated at room temperature. The disulfide-containing peptides were formed in excellent oxidation yields and were easily separated by filtration upon completion of the reaction. Excellent reusability of TentaGel-Pt(IV) was also achieved. The mechanism for construction of the disulfide bond in peptides via TentaGel-Pt(IV) oxidation was proposed.
Photochemical control of RNA structure by disrupting π-stacking
Resendiz, Marino J. E.,Schoen, Arne,Freire, Ernesto,Greenberg, Marc M.
supporting information; experimental part, p. 12478 - 12481 (2012/09/05)
Photolabile nucleotides that disrupt nucleic acid structure are useful mechanistic probes and can be used as tools for regulating biochemical processes. Previous probes can be limited by the need to incorporate multiple modified nucleotides into oligonucleotides and in kinetic studies by the rate-limiting step in the conversion to the native nucleotide. Photolysis of aryl sulfide 1 produces high yields of 5-methyluridine, and product formation is complete in less than a microsecond. Aryl sulfide 1 prevents RNA hairpin formation and complete folding of the preQ1 class I riboswitch. Proper folding is achieved in each instance upon photolysis at 350 nm. Aryl sulfide 1 is a novel tool for modulating RNA structure, and formation of 5-methyluridine within a radical cage suggests that it will be useful in kinetic studies.
Synthesis of diaryl disulfides via mild reduction of arylsulfinates with hydrazine monohydrate in DMSO
Zhu, Rui-Heng,Shi, Xiao-Xin
experimental part, p. 1108 - 1114 (2012/04/04)
Arylsulfinates were reduced with hydrazine monohydrate at room temperature in dimethylsulfoxide (DMSO) to afford diaryl disulfides in good yields. A dramatic solvent effect was observed, and DMSO was found to be the best solvent for the reaction. Copyright Taylor & Francis Group, LLC.
RADIKALIONEN 89. EINELEKTRONEN-OXIDATIONEN VON DIARYLDISULFIDEN MIT AlCl3/H2CCl2
Bock, Hans,Rittmeyer, Peter
, p. 261 - 292 (2007/10/02)
The single electron oxidation of 14 alkyl and alkoxy substituted diaryldisulfides by AlCl3/H2CCl2 has been investigated by ESR/ENDOR spectroscopy.The radical cations observed prove the following skeletal rearrangements: Those with ring hydrogens in ortho positions to the disulfide bridge preferentially form thianthrene derivatives.The isomeric dinaphthyl disulfides react differently, the 2,2'-isomer yielding the dibenzothianthrene radical cation and the 1,1'-isomer the well-known naphthalene-1,8-disulfide radical cation.For all diaryl disulfides with completely alkyl- or methoxy-blocked ortho positions, oxidative desulfuration is observed.As substantiated by additional (2)D and (33)S isotope marking, the bis(2,5-dimethoxyphenyl)disulfide reacts both to the corresponding thianthrene derivative as well as via desulfuration to the radical cation of the monosulfide.Accompanying cyclovoltammetric and photoelectron spectroscopic measurements prove that all ESR spectroscopically detected radical cations result from compounds Ar-S-Ar, Ar-SS-Ar and Ar(S)2Ar with rather low oxidation or ionisation potentials and thus suggest that each the most easily oxidized paramagnetic species is observed in the rather complex product mixtures, which form on AlCl3/H2CCl2 oxidation of diaryldisulfides. Key words: Diaryl disulfides; one-electron oxidation; radical cations; ESR/ENDOR spectra.
Radical Ions, 81. ENDOR Spectroscopic Investigations of Radical Cations of Aromatic Organosulfur Compounds
Bock, H.,Hierholzer, B.,Rittmeyer, P.
, p. 187 - 204 (2007/10/02)
Conditions for ENDOR measurements of organosulfur radical cations are discussed and tested.The one electron oxidation of a variety of aromatic sulfur compounds comprising benzene-1,2-dithiole, 1,4-dithiine, thianthrene and diphenylsulfide derivatives as well as 33S isotope-marked bis(2,5-dimethoxyphenyl)disulfide is accomplished using the oxygen-free, powerful and selective AlCl3/H2CCl2 reagent.Partly with substantial structural changes, paramagnetic M.+ species of 1,2-benzodithiete, 1,4-dithiine, thianthrene and diphenyl sulfide result.Their temperature-dependent ENDOR signal patterns provide numerous information e.g. on radical cation structure and dynamics, on the rather high sulfur spin populations or on the spin rotation interaction dominated relaxation behaviour.Accordingly, to obtain optimum ENDOR effects in organosulfur radical cations low temperature measurements are required, and especially for still undiscovered 33S ENDOR couplings, small g factor anisotropies and 33S spin densities appear to be necessary. - Keywords: ENDOR (Special, General Triple) Spectra, Temperature Dependence, Organosulfur Radical Cations, Structural Changes, Molecular Dynamics
