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Search for "disulfide" in Full Text gives 201 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

1,4-Dithianes: attractive C2-building blocks for the synthesis of complex molecular architectures

  • Bram Ryckaert,
  • Ellen Demeyere,
  • Frederick Degroote,
  • Hilde Janssens and
  • Johan M. Winne

Beilstein J. Org. Chem. 2023, 19, 115–132, doi:10.3762/bjoc.19.12

Graphical Abstract
  • acetylacetone (19, Scheme 5c) [39]. As mentioned in the Introduction, the metalation of 1,4-dithianes is quite problematic [12][16]. In the unsaturated 1,4-dithiin series, however, the metalation of the cyclic vinyl-1,2-disulfide moiety is somewhat more feasible. Even though linear vinyl-1,2-disulfides such as
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Published 02 Feb 2023

Redox-active molecules as organocatalysts for selective oxidative transformations – an unperceived organocatalysis field

  • Elena R. Lopat’eva,
  • Igor B. Krylov,
  • Dmitry A. Lapshin and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2022, 18, 1672–1695, doi:10.3762/bjoc.18.179

Graphical Abstract
  • radical (SPyf, Scheme 24) was proposed as a hydrogen atom abstracting agent for unactivated C–H bonds of alkanes and other CH-reagents [123] (Scheme 24). It was generated by the irradiation of the corresponding disulfide with 400 nm LEDs. In the proposed catalytic cycle tetrafluoropyridinyl thiol HSPyf is
  • reoxidized to the disulfide by (NH4)2S2O8. The disulfide (SPyf)2 is also consumed in the thiolation of C-centered radicals affording the SPyf radical and target sulfides, which are in turn useful C-centered radical precursors for photoredox-catalyzed reactions [123]. The high efficiency of the thiolation
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Perspective
Published 09 Dec 2022

Microelectrode arrays, electrosynthesis, and the optimization of signaling on an inert, stable surface

  • Kendra Drayton-White,
  • Siyue Liu,
  • Yu-Chia Chang,
  • Sakashi Uppal and
  • Kevin D. Moeller

Beilstein J. Org. Chem. 2022, 18, 1488–1498, doi:10.3762/bjoc.18.156

Graphical Abstract
  • of a Cu(I) precursor, and then confined to the surface of those electrodes with the use of a solution-phase Cu(II)-mediated disulfide bond-forming reaction using excess substrate in solution. The molecules were placed by individually addressable blocks of electrodes on the array that were each
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Published 20 Oct 2022

Synthesis of C6-modified mannose 1-phosphates and evaluation of derived sugar nucleotides against GDP-mannose dehydrogenase

  • Sanaz Ahmadipour,
  • Alice J. C. Wahart,
  • Jonathan P. Dolan,
  • Laura Beswick,
  • Chris S. Hawes,
  • Robert A. Field and
  • Gavin J. Miller

Beilstein J. Org. Chem. 2022, 18, 1379–1384, doi:10.3762/bjoc.18.142

Graphical Abstract
  • active site thiohemiaminal (amine to imine oxidation) or disulfide formation, respectively. Additionally, C6–Cl derivative 9 could probe cysteine alkylation. Reported herein is our exploration of this synthesis and the evaluation of GDP 6-chloro-6-deoxy-ᴅ-mannose 18 against GMD. Results and Discussion
  • modifying C6 [4]. Substrate 18 was known to form a disulfide in solution [10], presumably resulting in the glycosyl-1-phosphate being unable to access the enzyme active site; unfortunately, the addition of higher concentrations of reducing agent (DTT) and solid-supported PPh3 to access the reduced form for
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Published 30 Sep 2022

Polymer and small molecule mechanochemistry: closer than ever

  • José G. Hernández

Beilstein J. Org. Chem. 2022, 18, 1225–1235, doi:10.3762/bjoc.18.128

Graphical Abstract
  • to promote the thermodynamically disfavored SN2 cleavage of an individual protein disulfide bond by poorly nucleophilic organic thiols [21]. On the other hand, as for the connection or correlation between polymer and small molecule mechanochemistry, this Perspective article discusses recent studies
  • for the fullerenes to pass through. However, the capsule 5 is sensitive to mechanochemical stress due to the porosity, conformational rigidity, and due to the presence of hydrazone and/or disulfide moieties that act as mechanophores. Therefore, during ball milling, 5 gets partially disintegrated at
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Perspective
Published 14 Sep 2022

Derivatives of benzo-1,4-thiazine-3-carboxylic acid and the corresponding amino acid conjugates

  • Péter Kisszékelyi,
  • Tibor Peňaška,
  • Klára Stankovianska,
  • Mária Mečiarová and
  • Radovan Šebesta

Beilstein J. Org. Chem. 2022, 18, 1195–1202, doi:10.3762/bjoc.18.124

Graphical Abstract
  • directly. To that end, we attempted reactions from aminothiol 8a as well as from the corresponding disulfide, both at room temperature and under MWI. In these experiments, the yield of dimer 11a was in the range of 10–34%. We also tried to enhance the oxidative dimerization using a mild oxidizing agent
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Published 09 Sep 2022

Cholyl 1,3,4-oxadiazole hybrid compounds: design, synthesis and antimicrobial assessment

  • Anas J. Rasras,
  • Mohamed El-Naggar,
  • Nesreen A. Safwat and
  • Raed A. Al-Qawasmeh

Beilstein J. Org. Chem. 2022, 18, 631–638, doi:10.3762/bjoc.18.63

Graphical Abstract
  • available cholic acid, which was converted to its cholyl hydrazide (1) as previously reported by us [21]. The produced cholyl hydrazide 1 was heterocyclized to 1,3,4-oxadiazole-2-thiol 2 in excellent yield (93%), via the treatment with carbon disulfide and trimethylamine in refluxing ethanol (Scheme 1) [33
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Published 31 May 2022

Menadione: a platform and a target to valuable compounds synthesis

  • Acácio S. de Souza,
  • Ruan Carlos B. Ribeiro,
  • Dora C. S. Costa,
  • Fernanda P. Pauli,
  • David R. Pinho,
  • Matheus G. de Moraes,
  • Fernando de C. da Silva,
  • Luana da S. M. Forezi and
  • Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43

Graphical Abstract
  • respective ditellurides, a disulfide and a diselenide (Scheme 27). Recently, Ribeiro and co-workers used menadione as a nucleophile for the synthesis of 3-chloromethylated menadione 84, a key intermediate used to prepare selenium-menadione conjugates 86 [128]. In this work, compound 84 was prepared through
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Published 11 Apr 2022

Synthesis and late stage modifications of Cyl derivatives

  • Phil Servatius and
  • Uli Kazmaier

Beilstein J. Org. Chem. 2022, 18, 174–181, doi:10.3762/bjoc.18.19

Graphical Abstract
  • naturally occurring HDAC inhibitors contain sulfur moieties like, e.g., disulfides or thioesters. They seem to lack a zinc-chelating group at first sight, but the disulfide or thioester acts as a prodrug and are reduced/cleaved in vivo to liberate the free thiol, a strong Zn-binding group [24][25]. Results
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Published 04 Feb 2022

Peptide stapling by late-stage Suzuki–Miyaura cross-coupling

  • Hendrik Gruß,
  • Rebecca C. Feiner,
  • Ridhiwan Mseya,
  • David C. Schröder,
  • Michał Jewgiński,
  • Kristian M. Müller,
  • Rafał Latajka,
  • Antoine Marion and
  • Norbert Sewald

Beilstein J. Org. Chem. 2022, 18, 1–12, doi:10.3762/bjoc.18.1

Graphical Abstract
  • ], disulfide- [13], thioether- [14][15][16][17][18][19][20], triazole- [21][22], oxime- [23] and hydrazone formation [24] as well as multicomponent reactions such as the Ugi- or Petasis reaction [25][26][27][28][29][30][31][32]. The content of helicity can moreover be changed by the introduction of a photo
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Published 03 Jan 2022

Catalyzed and uncatalyzed procedures for the syntheses of isomeric covalent multi-indolyl hetero non-metallides: an account

  • Ranadeep Talukdar

Beilstein J. Org. Chem. 2021, 17, 2102–2122, doi:10.3762/bjoc.17.137

Graphical Abstract
  • for accessing bis(indolyl)sulfides. To synthesize the unsymmetrical bis(indolyl)sulfide 88, Janosik reacted the indole disulfide 87 with free indole and obtained the product 88 in 81% yield, where the sulfur linkages were 2,3’- with respect to the two indole nuclei (Scheme 11a) [73][74][75][76]. Hall
  • compounds having semiconductor properties [80]. The syntheses of these compounds were studied by Janosik in 2006. The N-silyl-protected 3-bromoindole 93 was subjected to strong basic medium (t-BuLi) at low temperature and then quenched with either bis(phenylsulfonyl)sulfide (83) or indole disulfide 94
  • the sulfur species 102 takes place to generate copper sulfide complex 103. An oxidative homocoupling gives the bis(indol-3-yl)sulfide 101. Simultaneously, an oxidative homocoupling of the copper sulfide complex can take place to afford disulfide 104, that reacts with N-methylindole again under
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Published 19 Aug 2021

Natural products in the predatory defence of the filamentous fungal pathogen Aspergillus fumigatus

  • Jana M. Boysen,
  • Nauman Saeed and
  • Falk Hillmann

Beilstein J. Org. Chem. 2021, 17, 1814–1827, doi:10.3762/bjoc.17.124

Graphical Abstract
  • , temperature and aeration, are known to regulate gliotoxin biosynthesis [115][119][120]. The biological activity of ETP’s like gliotoxin is mediated by the active disulfide bridge that targets vulnerable thiols or catalyses oxidative burst formation via redox cycling [78]. In previous studies, these cytotoxic
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Published 28 Jul 2021

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

  • Nikita Brodyagin,
  • Martins Katkevics,
  • Venubabu Kotikam,
  • Christopher A. Ryan and
  • Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

Graphical Abstract
  • disulfide linkages to transportan and penetratin peptides. The PNA–peptide conjugates were effectively internalized in human Bowes melanoma cells and in vivo in rats [171]. Transportan peptide localized the PNA in membranous structures of cells, while the penetratin conjugate preferred nuclear localization
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Published 19 Jul 2021

A recent overview on the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles

  • Pezhman Shiri,
  • Ali Mohammad Amani and
  • Thomas Mayer-Gall

Beilstein J. Org. Chem. 2021, 17, 1600–1628, doi:10.3762/bjoc.17.114

Graphical Abstract
  • disulfide (97) was reported by Xu et al. The reaction has been achieved using a catalytic amount of CuI, LiOt-Bu, and 4 Å molecular sieves in THF as solvent at 40 °C under N2 atmosphere for 12 h and proceeds via a multicomponent CuAAC/persulfuration sequence. The strategy features a wide substrate scope
  • ) [55]. A probable mechanism for this transformation was proposed as illustrated in Scheme 29. The cycloaddition reaction between copper(I) acetylide 99 and organic azide 95 occurs to obtain the triazole cuprate intermediate 100, which reacts as a nucleophile with the disulfide electrophile 97 to
  • produce the corresponding triazole disulfide 98 [55]. A convenient route to triazole-fused sultams 104 was reported by Latyshev et al. It comprises a modified CuIAAC cycloaddition to produce intermediate sulfonamide-tethered 5-iodo-1,2,3-triazoles 103, followed by a base-mediated cyclization under
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Published 13 Jul 2021

Double-headed nucleosides: Synthesis and applications

  • Vineet Verma,
  • Jyotirmoy Maity,
  • Vipin K. Maikhuri,
  • Ritika Sharma,
  • Himal K. Ganguly and
  • Ashok K. Prasad

Beilstein J. Org. Chem. 2021, 17, 1392–1439, doi:10.3762/bjoc.17.98

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Published 08 Jun 2021

Synthetic reactions driven by electron-donor–acceptor (EDA) complexes

  • Zhonglie Yang,
  • Yutong Liu,
  • Kun Cao,
  • Xiaobin Zhang,
  • Hezhong Jiang and
  • Jiahong Li

Beilstein J. Org. Chem. 2021, 17, 771–799, doi:10.3762/bjoc.17.67

Graphical Abstract
  • step without any transition-metal catalyst, ligand, or photocatalyst, this method possesses a splendid application prospect. The reaction mechanism is as follows (Scheme 48): Firstly, carbon disulfide combines with N-methylaniline (134) in the presence of Cs2CO3 to form thiolate 136. Thiolate 136 is
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Published 06 Apr 2021

[2 + 1] Cycloaddition reactions of fullerene C60 based on diazo compounds

  • Yuliya N. Biglova

Beilstein J. Org. Chem. 2021, 17, 630–670, doi:10.3762/bjoc.17.55

Graphical Abstract
  • soluble in the majority of organic solvents and only partially soluble in carbon disulfide, which is expected to ultimately lead to similar insoluble hard-to-recover polymers. It is believed [95] that the best solution to the problem seems to involve the incorporation of solubilizing groups into the
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Published 05 Mar 2021

Valorisation of plastic waste via metal-catalysed depolymerisation

  • Francesca Liguori,
  • Carmen Moreno-Marrodán and
  • Pierluigi Barbaro

Beilstein J. Org. Chem. 2021, 17, 589–621, doi:10.3762/bjoc.17.53

Graphical Abstract
  • Polystyrene (PS): PS is a low-cost, hard and brittle plastic used both as a solid or foam in protective packaging, containers and trays [151]. It is a nonbiodegradable material accounting for about 10% of municipal solid waste [135]. It is soluble in benzene, carbon disulfide, chlorinated hydrocarbons, lower
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Published 02 Mar 2021

Breakdown of 3-(allylsulfonio)propanoates in bacteria from the Roseobacter group yields garlic oil constituents

  • Anuj Kumar Chhalodia and
  • Jeroen S. Dickschat

Beilstein J. Org. Chem. 2021, 17, 569–580, doi:10.3762/bjoc.17.51

Graphical Abstract
  • structures of the garlic oil constituents and also of the allyl group remained unknown, but its formula was correctly assigned as C3H5. Five decades later, Semmler reported on the nature of allyl propyl disulfide (1), diallyl disulfide (2), diallyl trisulfide (3), and diallyl tetrasulfide (4) from garlic oil
  • (Scheme 1A) [2]. The antibacterial principle in garlic was identified in 1944 by Cavallito et al. as allicin (5) [3], a formal oxidation product of disulfide 2. Not only 5, but also several other sulfur compounds from garlic are today known to exhibit diverse biological activities, including inter alia
  • labelling into dimethyl disulfide (DMDS), the oxidative dimerization product from MeSH, showing the activity of the demethylation pathway in these bacteria. However, knockout of the dmdA gene in R. pomeroyi still gave a low incorporation of labelling into DMDS, suggesting the presence of another gene
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Published 26 Feb 2021

Metal-free visible-light-enabled vicinal trifluoromethyl dithiolation of unactivated alkenes

  • Xiaojuan Li,
  • Qiang Zhang,
  • Weigang Zhang,
  • Jinzhu Ma,
  • Yi Wang and
  • Yi Pan

Beilstein J. Org. Chem. 2021, 17, 551–557, doi:10.3762/bjoc.17.49

Graphical Abstract
  • of blue LEDs, allyl boronate 1a (0.1 mmol), disulfide 2a (1.0 equiv) and N-(trifluoromethylthio)phthalimide (Phth-SCF3, 3, 1.5 equiv), the desired trifluoromethylthiolated product 4a was obtained in 71% yield with 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN, 2 mol %) as the
  • unactivated alkenes to give the intermediate B. The subsequent addition of B to disulfide 2 affords the difunctionalized products 4 or 5 and the thiophenyl radical C [52]. Finally, the oxidation of radical C by 4CzIPN+ closes the catalytic cycle [53]. Conclusion In summary, we described a visible-light
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Published 24 Feb 2021

Identification of volatiles from six marine Celeribacter strains

  • Anuj Kumar Chhalodia,
  • Jan Rinkel,
  • Dorota Konvalinkova,
  • Jörn Petersen and
  • Jeroen S. Dickschat

Beilstein J. Org. Chem. 2021, 17, 420–430, doi:10.3762/bjoc.17.38

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  • ·OEt2-catalyzed reaction of bis(benzothiazol-2-yl)disulfane with dimethyl disulfide, giving access to 41 with a yield of 64% (Scheme 2). The synthetic compound 41 showed an identical mass spectrum and retention index compared to the volatile in the Celeribacter extracts. The Z and E stereoisomers of 42
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Published 11 Feb 2021

Recent progress in the synthesis of homotropane alkaloids adaline, euphococcinine and N-methyleuphococcinine

  • Dimas J. P. Lima,
  • Antonio E. G. Santana,
  • Michael A. Birkett and
  • Ricardo S. Porto

Beilstein J. Org. Chem. 2021, 17, 28–41, doi:10.3762/bjoc.17.4

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  • -Ni (W-2), H2O, 30 °C, 95%; vii) PCC, CH2Cl2, rt, 30%. Synthesis (+)-euphococcinine (2). Reagents and conditions: i) 2,4-bis(4-phenoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide (Belleau’s reagent), 100%; ii) 33, triethylamine, trimethyl phosphite, reflux, 69%; iii) H2 (60 psi), Pt/C, Na2CO3
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Published 05 Jan 2021

3-Acetoxy-fatty acid isoprenyl esters from androconia of the ithomiine butterfly Ithomia salapia

  • Florian Mann,
  • Daiane Szczerbowski,
  • Lisa de Silva,
  • Melanie McClure,
  • Marianne Elias and
  • Stefan Schulz

Beilstein J. Org. Chem. 2020, 16, 2776–2787, doi:10.3762/bjoc.16.228

Graphical Abstract
  • acylium ion m/z 263 is formed. In contrast, isoprenyl esters lack the M − 69 ion, but additionally show acylium +1 and +2 ions (m/z 264 and 265 in A). The location of the double bonds in the unsaturated esters was determined by dimethyl disulfide (DMDS) addition [25][26]. Because the double bond in the
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Published 16 Nov 2020

Optical detection of di- and triphosphate anions with mixed monolayer-protected gold nanoparticles containing zinc(II)–dipicolylamine complexes

  • Lena Reinke,
  • Julia Bartl,
  • Marcus Koch and
  • Stefan Kubik

Beilstein J. Org. Chem. 2020, 16, 2687–2700, doi:10.3762/bjoc.16.219

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  • and Discussion Ligand synthesis. The ligands used in this work are depicted in Figure 1. All of them derived from lipoic acid, which was chosen as the anchor group because the immobilization of a cyclic disulfide on gold involves the formation of two Au–S bonds, causing the ligands to have a smaller
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Published 02 Nov 2020

Selective and reversible 1,3-dipolar cycloaddition of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with 1,3-diphenylprop-2-en-1-ones under microwave irradiation

  • Alexander P. Molchanov,
  • Mariia M. Efremova,
  • Mariya A. Kryukova and
  • Mikhail A. Kuznetsov

Beilstein J. Org. Chem. 2020, 16, 2679–2686, doi:10.3762/bjoc.16.218

Graphical Abstract
  • with carbon disulfide [26], diphenylketene [27], β-nitrostyrenes [28][29], if ionic liquids (IL) were used as reaction media. The reaction of β-nitrostyrenes with azomethine imines proceeds giving mixtures of Michael and anti-Michael-type adducts, containing a nitro group at the C2- or C1-position of
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Published 30 Oct 2020
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