A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis

• Nian Li,
• Ruzal Sitdikov,
• Ajit Prabhakar Kale,
• Joost Steverlynck,
• Bo Li and
• Magnus Rueping

Beilstein J. Org. Chem. 2024, 20, 2500–2566, doi:10.3762/bjoc.20.214

• electrolyte, and carbon felt and platinum plate as electrodes, the intramolecular hydroamination proceeded smoothly, yielding azetidines in moderate to good yields. This method was applied to the LSF of celecoxib, zonisamide, and dansyl amide (Scheme 33a). Additionally, the allylation of aldehydes also

Selected peptide-based fluorescent probes for biological applications

• Debabrata Maity

Beilstein J. Org. Chem. 2020, 16, 2971–2982, doi:10.3762/bjoc.16.247

• a dansyl acceptor, for ratiometric detection of dsDNA (Figure 4 [33]. Compound 3 contains two Gly–Ser–Lys tripeptide arms attached via their C-terminus to a central lysine spacer (Figure 4A). Compound 3 is in unfolded form in unbound conditions as it exhibits the naphthalene emission at 383 nm upon

• arms attached through their C-terminus to a central lysine. Two heparin sensors 10 and 11 are developed by attaching the N-terminus of the peptide beacon with pyrenes and fluorescence resonance energy transfer (FRET) pair (naphthalene and dansyl), respectively for ratiometric detection of heparin

• and a dansyl acceptor for 11 (Figure 9A and Figure 9B). A minimum 30 nM of heparin can be detected by using 10 or 11. The reported binding constants for 10 and 11 with heparin are 1.3 × 106 M−1 and 2.9 × 106 M−1, respectively. Sensors 10 and 11 are highly selective for the heparin detection over other

Archangelolide: A sesquiterpene lactone with immunobiological potential from Laserpitium archangelica

• Silvie Rimpelová,
• Michal Jurášek,
• Lucie Peterková,
• Jiří Bejček,
• Vojtěch Spiwok,
• Miloš Majdl,
• Michal Jirásko,
• Miloš Buděšínský,
• Juraj Harmatha,
• Eva Kmoníčková,
• Pavel Drašar and
• Tomáš Ruml

Beilstein J. Org. Chem. 2019, 15, 1933–1944, doi:10.3762/bjoc.15.189

• studied by us and others, there are only scarce reports on the biological activity of archangelolide. Here we present the preparation of its fluorescent derivative based on a dansyl moiety using azide–alkyne Huisgen cycloaddition having obtained the two sesquiterpene lactones from the seeds of Laserpitium

• archangelica Wulfen using supercritical CO2 extraction. We show that dansyl-archangelolide localizes in the endoplasmic reticulum of living cells similarly to trilobolide; localization in mitochondria was also detected. This led us to a more detailed study of the anticancer potential of archangelolide

• . Interestingly, we found that neither archangelolide nor its dansyl conjugate did exhibit cytotoxic effects in contrast to the structurally closely related counterparts trilobolide and thapsigargin. We explain this observation by a molecular dynamics simulation, in which, in contrast to trilobolide

An overview of recent advances in duplex DNA recognition by small molecules

• Sayantan Bhaduri,
• Nihar Ranjan and
• Dev P. Arya

Beilstein J. Org. Chem. 2018, 14, 1051–1086, doi:10.3762/bjoc.14.93

• and its cytotoxicity was attributed to DNA minor groove binding ability [105]. Recently, Schmuck et al. have developed a first prototype of cationic oligopeptide-based molecular beacon (conjugate 43) coupled with a FRET pair, a naphthalene donor and a dansyl acceptor, for ratiometric detection of ds

Azobenzene-based inhibitors of human carbonic anhydrase II

• Leander Simon Runtsch,
• David Michael Barber,
• Peter Mayer,
• Michael Groll,
• Dirk Trauner and
• Johannes Broichhagen

Beilstein J. Org. Chem. 2015, 11, 1129–1135, doi:10.3762/bjoc.11.127

• dansyl competition assay is employed for this purpose [1][14]. However, as this assay is fluorescence-based and azobenzenes can quench fluorescence [15], this might cause a distortion in the obtained data. Furthermore, irradiation with UV light (i.e., λ = 280 nm for tryptophan excitation) can result in

A small azide-modified thiazole-based reporter molecule for fluorescence and mass spectrometric detection

• Stefanie Wolfram,
• Hendryk Würfel,
• Stefanie H. Habenicht,
• Christine Lembke,
• Phillipp Richter,
• Eckhard Birckner,
• Rainer Beckert and
• Georg Pohnert

Beilstein J. Org. Chem. 2014, 10, 2470–2479, doi:10.3762/bjoc.10.258

• unproblematic toxicology they have almost completely replaced radioactive tags. Widely used representatives include dansyl chloride, fluoresceins, rhodamines and boron-dipyrromethenes (BODIPYs) [1]. Dansyl chloride, with a maximum UV–vis absorption at 369 nm, is one of the first extrinsic fluorescent dyes

• . For comparison, we also synthesized and tested a bromine modified dansyl derivative N-(3-azidopropyl)-6-bromo-5-(dimethylamino)naphthalene-1-sulfonamide (BNS, 6, Figure 2). Dansyl chloride is brominated according to the literature [30] to produce 6-bromo-5-(dimethylamino)naphthalene-1-sulfonyl

• . Derivatization with dansyl chloride is used for labeling of primary and secondary amines or phenols resulting in enhanced ESI signals and shifted retention times of labeled polar analytes in reversed-phase LC [27]. For comparison with BPT (1) we also introduced bromine into the aromatic system of DNS (8) to

Silver and gold-catalyzed multicomponent reactions

• Giorgio Abbiati and
• Elisabetta Rossi

Beilstein J. Org. Chem. 2014, 10, 481–513, doi:10.3762/bjoc.10.46

• ] complex (HC^N = 2-benzylpyridine) in water at 40 °C. The reaction yields ranged from good to excellent, and the method allowed the introduction of alkynes and amines properly functionalized with particular groups,(i.e., dansyl and biotin), or m/p-ethynylbenzenes, suitable for further orthogonal

Advancements in the mechanistic understanding of the copper-catalyzed azide–alkyne cycloaddition

• Regina Berg and
• Bernd F. Straub

Beilstein J. Org. Chem. 2013, 9, 2715–2750, doi:10.3762/bjoc.9.308

• mechanistic proposals: computational and experimental evidence The groups of Fokin and Finn have tested different heterocyclic chelating ligands for CuAAC by fluorescence quenching in the reaction of dansyl azide fluorophore and dabsyl alkyne, and carried out kinetic measurements with a bis

A peptidic hydrogel that may behave as a “Trojan Horse”

• Nicola Castellucci,
• Giorgio Sartor,
• Natalia Calonghi,
• Carola Parolin,
• Giuseppe Falini and
• Claudia Tomasini

Beilstein J. Org. Chem. 2013, 9, 417–424, doi:10.3762/bjoc.9.44

• confocal microscopy, fluorescent hydrogels were prepared, introducing the fluorescent dansyl moiety into the mixture. Keywords: amino acids; confocal microscopy; controlled release; hydrogel; low molecular weight hydrogelator; Introduction Drug delivery is an important topic in the finding of successful

• by confocal laser scanning microscopy, we prepared also three fluorescent compounds B, C and D, all containing the fluorescent dansyl group (Dans) [24]. First we prepared hydrogels 1 and 2 (Table 1), both containing A and a mixture of water and ethanol in 9:1 ratio and 1:1 ratio, respectively. Both

• sol status, due to the almost complete ionization of the carboxylate groups [25]. Then, following the same method, we attempted to prepare hydrogels containing the fluorescent dansyl group (Dans). First we tried with pure B (Table 1, entries 3–6), but we could verify that B is not as good a gelator as

Spin state switching in iron coordination compounds

• Philipp Gütlich,
• Ana B. Gaspar and
• Yann Garcia

Beilstein J. Org. Chem. 2013, 9, 342–391, doi:10.3762/bjoc.9.39

Synthesis of dye/fluorescent functionalized dendrons based on cyclotriphosphazene

• Aurélien Hameau,
• Sabine Fuchs,
• Régis Laurent,
• Jean-Pierre Majoral and
• Anne-Marie Caminade

Beilstein J. Org. Chem. 2011, 7, 1577–1583, doi:10.3762/bjoc.7.186

• Functionalized phenols based on tyramine were synthesized in order to be selectively grafted on to hexachlorocyclotriphosphazene, affording a variety of functionalized dendrons of type AB5. The B functions comprised fluorescent groups (dansyl) or dyes (dabsyl), whereas the A function was provided by either an

• aldehyde or an amine. The characterization of these dendrons is reported. An unexpected behaviour of a fluorescent and water-soluble dendron based on dansyl groups in mixtures of dioxane/water was observed. Keywords: dabsyl; dansyl; dendrimer; dendron; fluorescence; Introduction Dendrimers constitute an

• grafted as terminal groups on to dendrimers. In particular the dansyl group has been frequently used to functionalize poly(propyleneimine) [7][8], poly(lysine) [9], poly(amidoamine) [10], and poly(melamine) [11] dendrimers. It has been shown that no interaction occurs between these terminal fluorophores

Anion receptors containing thiazine-1,1-dioxide heterocycles as hydrogen bond donors

• Hong-Bo Wang,
• James A. Wisner and
• Michael C. Jennings

Beilstein J. Org. Chem. 2010, 6, No. 50, doi:10.3762/bjoc.6.50

• benzenesulfonyl, toluenesulfonyl, dansyl, and benzenedisulfonyl chlorides [8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23]. We have recently investigated thiazine-1,1-dioxide heterocycles (Figure 1A) as hydrogen bond donor groups in the formation of double helical complexes [24]. The parent

Molecular recognition of organic ammonium ions in solution using synthetic receptors

• Andreas Späth and
• Burkhard König

Beilstein J. Org. Chem. 2010, 6, No. 32, doi:10.3762/bjoc.6.32

Synthesis of lipophilic 1-deoxygalactonojirimycin derivatives as D-galactosidase inhibitors

• Georg Schitter,
• Elisabeth Scheucher,
• Andreas J. Steiner,
• Arnold E. Stütz,
• Martin Thonhofer,
• Chris A. Tarling,
• Stephen G. Withers,
• Jacqueline Wicki,
• Katrin Fantur,
• Eduard Paschke,
• Don J. Mahuran,
• Brigitte A. Rigat,
• Michael Tropak and
• Tanja M. Wrodnigg

Beilstein J. Org. Chem. 2010, 6, No. 21, doi:10.3762/bjoc.6.21

• neurological deterioration [23]. Our studies revealed that 1-deoxy-D-galactonojirimycin-lysine hybrids, when carrying an aromatic substituent, such as a dansyl moiety, in its nature a lipophilic aromatic substituent, are potent D-galactosidase inhibitors and also show activity with human lysosomal β