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Search for "functionality" in Full Text gives 613 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Potent hemithioindigo-based antimitotics photocontrol the microtubule cytoskeleton in cellulo

  • Alexander Sailer,
  • Franziska Ermer,
  • Yvonne Kraus,
  • Rebekkah Bingham,
  • Ferdinand H. Lutter,
  • Julia Ahlfeld and
  • Oliver Thorn-Seshold

Beilstein J. Org. Chem. 2020, 16, 125–134, doi:10.3762/bjoc.16.14

Graphical Abstract
  • effects, due to its many survival-critical roles, as well as non-functionality of the modified tubulin product. For example, knockout approaches have only been described for single isoforms of α/β-tubulin, and these cannot deliver the dynamic reversibility and effect-specificity that is required for
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Published 27 Jan 2020

Photocontrolled DNA minor groove interactions of imidazole/pyrrole polyamides

  • Sabrina Müller,
  • Jannik Paulus,
  • Jochen Mattay,
  • Heiko Ihmels,
  • Veronica I. Dodero and
  • Norbert Sewald

Beilstein J. Org. Chem. 2020, 16, 60–70, doi:10.3762/bjoc.16.8

Graphical Abstract
  • peptides or small molecules, thereby controlling geometry and functionality. E-to-Z photoisomerization usually is achieved upon irradiation at 350 nm (π–π* transition), while the Z-to-E isomerization proceeds photochemically upon irradiation at >400 nm (n–π* transition) or thermally. Photoswitchable
  • substance, once located at the DNA target, with an external stimulus. Azobenzenes are photoswitchable molecules capable of generating significant structural changes in peptides or small molecules, thereby controlling their geometry and functionality upon irradiation [10][11][12][13]. While isomerization of
  • was proven amenable for the light-induced triggering of transcription [24], photoswitchable polyamides that can act as selective DNA minor groove binders displaying tunable affinity have not yet been reported [29][30]. We envisaged that control of the geometry and functionality could be achieved upon
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Published 09 Jan 2020

SnCl4-catalyzed solvent-free acetolysis of 2,7-anhydrosialic acid derivatives

  • Kesatebrhan Haile Asressu and
  • Cheng-Chung Wang

Beilstein J. Org. Chem. 2019, 15, 2990–2999, doi:10.3762/bjoc.15.295

Graphical Abstract
  • distinguished these alcohols by selective protection of the OH-7 functionality as 2,7-anhydro-Neu5Ac, leaving position OH-4 free for glycosylation upon protection of the vicinal OH-8 and OH-9 substituents as benzylidene or acetonide rings [6]. The formation of the bicyclo[3.2.1] backbone of 2,7-anhydro-Neu5Ac
  • disaccharides were cleaved and acetylated, as shown in Scheme 5. The difficulty of these reactions might have been attributed to the more liable nature of the tertiary acetal center C-1 of fucose as compared to the sterically hindered quaternary ketal functionality C-2 of the 2,7-anhydro skeleton. To our
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Published 23 Dec 2019

Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica

  • Soleiman E. Helaly,
  • Wilawan Kuephadungphan,
  • Patima Phainuphong,
  • Mahmoud A. A. Ibrahim,
  • Kanoksri Tasanathai,
  • Suchada Mongkolsamrit,
  • Janet Jennifer Luangsa-ard,
  • Souwalak Phongpaichit,
  • Vatcharin Rukachaisirikul and
  • Marc Stadler

Beilstein J. Org. Chem. 2019, 15, 2968–2981, doi:10.3762/bjoc.15.293

Graphical Abstract
  • correlations from the methyl H-11 to H-3 and from H-3 to H-4, together with a series of HMBC correlations from H-11 to C-3/C-4, H-4 to C-4a/C-10a/C-5, H-5 to C-4/C-6/C-10a/C-9a, and from H-8 to C9/C-9a/C-6/C-7, confirmed the presence of the dihydro-α-naphthopyrone. The position of the dimethoxy functionality
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Published 16 Dec 2019

Two new aromatic polyketides from a sponge-derived Fusarium

  • Mada Triandala Sibero,
  • Tao Zhou,
  • Keisuke Fukaya,
  • Daisuke Urabe,
  • Ocky K. Karna Radjasa,
  • Agus Sabdono,
  • Agus Trianto and
  • Yasuhiro Igarashi

Beilstein J. Org. Chem. 2019, 15, 2941–2947, doi:10.3762/bjoc.15.289

Graphical Abstract
  • strong absorption band at 1683 cm−1, indicating the presence of carbonyl functionality. The 13C NMR exhibited 19 carbon signals that could be assigned to eleven nonprotonated sp2 carbons (seven are oxygenated), five sp2 methine carbons, one methylene carbon, and two methyl carbons from HSQC spectral data
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Published 09 Dec 2019

Chemical synthesis of tripeptide thioesters for the biotechnological incorporation into the myxobacterial secondary metabolite argyrin via mutasynthesis

  • David C. B. Siebert,
  • Roman Sommer,
  • Domen Pogorevc,
  • Michael Hoffmann,
  • Silke C. Wenzel,
  • Rolf Müller and
  • Alexander Titz

Beilstein J. Org. Chem. 2019, 15, 2922–2929, doi:10.3762/bjoc.15.286

Graphical Abstract
  • production. As previously mentioned, one reason for this could be high specificity of the biosynthetic machinery which might require a full length phosphopantetheine moiety or even a PCP bound substrate, for condensation to take place. To verify the functionality of the truncated argyrin biosynthesis operon
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Published 05 Dec 2019

One-pot synthesis of substituted pyrrolo[3,4-b]pyridine-4,5-diones based on the reaction of N-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-arylethyl)acetamide with amines

  • Valeriya G. Melekhina,
  • Andrey N. Komogortsev,
  • Boris V. Lichitsky,
  • Vitaly S. Mityanov,
  • Artem N. Fakhrutdinov,
  • Arkady A. Dudinov,
  • Vasily A. Migulin,
  • Yulia V. Nelyubina,
  • Elizaveta K. Melnikova and
  • Michail M. Krayushkin

Beilstein J. Org. Chem. 2019, 15, 2840–2846, doi:10.3762/bjoc.15.277

Graphical Abstract
  • developed, the obtained compounds were further employed in the synthesis of pyrrolopyridinones 1. The presence of the two key reactive groups in adjacent positions in 7, the acetamide moiety and the enaminoketone functionality, should allow for an intramolecular condensation and the formation of the target
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Published 25 Nov 2019

Chemical tuning of photoswitchable azobenzenes: a photopharmacological case study using nicotinic transmission

  • Lorenzo Sansalone,
  • Jun Zhao,
  • Matthew T. Richers and
  • Graham C. R. Ellis-Davies

Beilstein J. Org. Chem. 2019, 15, 2812–2821, doi:10.3762/bjoc.15.274

Graphical Abstract
  • activation with cycles of violet and green light. Due to the very long-lived metastable cis configuration, 4FAB in vivo use could be of great promise for long term biological studies. Further chemical functionalization of this 4FAB probe with a maleimide functionality allowed clean cross-linking with
  • ][20] compared to 2, so a simple one-step route can be used to install the maleimides. It is this functionality that allows coupling (often called "tethering", symbolized as "t" for tetherable in Scheme 1) of the probe with mutant proteins. In our case, we developed a three-step route to install the
  • ][13], specifically the spectral separation of the n–π* transitions of the trans and cis configurations. Since the maleimide functionality of 1 is quite hydrolytically sensitive at neutral pH, we characterized precursor 2. This photochrome underwent the expected trans–cis isomerization (Figure 2a). The
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Published 21 Nov 2019

A review of asymmetric synthetic organic electrochemistry and electrocatalysis: concepts, applications, recent developments and future directions

  • Munmun Ghosh,
  • Valmik S. Shinde and
  • Magnus Rueping

Beilstein J. Org. Chem. 2019, 15, 2710–2746, doi:10.3762/bjoc.15.264

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  • chirally modified electrodes Electrochemical oxidation reactions have long served as substantial synthetic tool because of their ability to increase the functionality of organic molecules via reversing the polarity of electron-rich functional groups and thereby generating highly reactive intermediates
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Published 13 Nov 2019

Fluorinated maleimide-substituted porphyrins and chlorins: synthesis and characterization

  • Valentina A. Ol’shevskaya,
  • Elena G. Kononova and
  • Andrei V. Zaitsev

Beilstein J. Org. Chem. 2019, 15, 2704–2709, doi:10.3762/bjoc.15.263

Graphical Abstract
  • the maleimide group with its rich biological activity to the tetrapyrrole macrocycles with their unique photophysical properties may result in new conjugates with improved chemical, biological and anticancer characteristics [28]. Moreover, maleimide is a stable functionality that rapidly and
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Published 13 Nov 2019

Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis

  • Heather J. Lacey,
  • Cameron L. M. Gilchrist,
  • Andrew Crombie,
  • John A. Kalaitzis,
  • Daniel Vuong,
  • Peter J. Rutledge,
  • Peter Turner,
  • John I. Pitt,
  • Ernest Lacey,
  • Yit-Heng Chooi and
  • Andrew M. Piggott

Beilstein J. Org. Chem. 2019, 15, 2631–2643, doi:10.3762/bjoc.15.256

Graphical Abstract
  • of was retrieved from AspGD [45] under the locus tag AO090026000582. AstC homologs were identified in A. nanangensis via the tBLASTn [44] functionality in Geneious 10.2.6 [46]. The genome sequences for drimane sesquiterpenoid producing Aspergilli were obtained from NCBI where available. This included
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Published 05 Nov 2019

A new approach to silicon rhodamines by Suzuki–Miyaura coupling – scope and limitations

  • Thines Kanagasundaram,
  • Antje Timmermann,
  • Carsten S. Kramer and
  • Klaus Kopka

Beilstein J. Org. Chem. 2019, 15, 2569–2576, doi:10.3762/bjoc.15.250

Graphical Abstract
  • widely used in the literature (see e.g. [30]); also the term Si-xanthone (for derivatives of 12) is established instead of 9-silaanthracen-10(9H)-one). The conditions tolerated also the use of the unprotected acid functionality of the boroxine 23b (23c, 31%, respectively 56% brsm), while application of
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Published 29 Oct 2019

Chemical synthesis of the pentasaccharide repeating unit of the O-specific polysaccharide from Escherichia coli O132 in the form of its 2-aminoethyl glycoside

  • Debasish Pal and
  • Balaram Mukhopadhyay

Beilstein J. Org. Chem. 2019, 15, 2563–2568, doi:10.3762/bjoc.15.249

Graphical Abstract
  • the target molecule. First, the phthalimido group was removed using ethylenediamine [26] followed by acetylation with Ac2O in the presence of pyridine [27] to furnish the desired acetamido functionality. Next, the benzylidene group was hydrolyzed using 80% AcOH at 80 ºC [28]. Further, Zemplén de-O
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Published 28 Oct 2019

In search of visible-light photoresponsive peptide nucleic acids (PNAs) for reversible control of DNA hybridization

  • Lei Zhang,
  • Greta Linden and
  • Olalla Vázquez

Beilstein J. Org. Chem. 2019, 15, 2500–2508, doi:10.3762/bjoc.15.243

Graphical Abstract
  • calculated for the unmodified PNA analogue (20). Unfortunately, no difference between isomers was observed. The potential of the functionality of our compounds could be enhanced by both changing the localization and the number of incorporated photoswitches. To try to maintain the cooperative base pairing, we
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Published 22 Oct 2019

Chiral terpene auxiliaries V: Synthesis of new chiral γ-hydroxyphosphine oxides derived from α-pinene

  • Anna Kmieciak and
  • Marek P. Krzemiński

Beilstein J. Org. Chem. 2019, 15, 2493–2499, doi:10.3762/bjoc.15.242

Graphical Abstract
  • ], conjugated additions to enones [7], and allylic alkylations [8][9]. Another direction of research is the use of phosphines in organocatalysis [10][11] and bifunctional catalysis [12]. Several methods were developed to introduce the phosphine functionality to organic molecules. The reaction of organometallics
  • and 18 were assigned using 1H,1H-COSY spectra. The configurations at C4 were established by correlations observed in their 1H,1H-NOESY spectra (Figure 1, Supporting Information File 1). Synthesis of γ-hydroxyphosphines The key step in the synthesis to introduce a phosphine functionality is the thermal
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Published 22 Oct 2019

Combining the Ugi-azide multicomponent reaction and rhodium(III)-catalyzed annulation for the synthesis of tetrazole-isoquinolone/pyridone hybrids

  • Gerardo M. Ojeda,
  • Prabhat Ranjan,
  • Pavel Fedoseev,
  • Lisandra Amable,
  • Upendra K. Sharma,
  • Daniel G. Rivera and
  • Erik V. Van der Eycken

Beilstein J. Org. Chem. 2019, 15, 2447–2457, doi:10.3762/bjoc.15.237

Graphical Abstract
  • in the Ugi-azide-4CR, see Scheme 1), with tetrazole/isoquinoline hybrids bearing a benzyl (4p), a p-methoxyphenyl (4q) or a tert-butyl (4r) group, respectively, being obtained in good yields. However, the presence of an ester functionality at the tetrazole ring (R1 = CH2CO2Me) led to a significant
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Published 16 Oct 2019

Sugar-derived oxazolone pseudotetrapeptide as γ-turn inducer and anion-selective transporter

  • Sachin S. Burade,
  • Sushil V. Pawar,
  • Tanmoy Saha,
  • Navanath Kumbhar,
  • Amol S. Kotmale,
  • Manzoor Ahmad,
  • Pinaki Talukdar and
  • Dilip D. Dhavale

Beilstein J. Org. Chem. 2019, 15, 2419–2427, doi:10.3762/bjoc.15.234

Graphical Abstract
  • converted to C-3-tetrasubstituted furanoid sugar azido ester 3 as per our reported protocol [12]. Hydrolysis of the ester functionality in 3 with LiOH at room temperature afforded azido acid 4a in 92% yield, while hydrogenation of 3 using 10% Pd/C in MeOH at room temperature for 3 h afforded the amino ester
  • to the amide NH(I) and NH(II), respectively. The signal at δ 1.80 ppm, integrating for two protons, was assigned to the presence of an NH2 functionality. In the 13C NMR spectrum, the appearance of signals at δ 170.8, 170.6 and 166.7 ppm were assigned to the lactone/amide carbonyl functionalities. The
  • signal at δ 163.0 ppm was assigned to the -C=N functionality. The 1H,15N-HSQC and 1H,15N-HMBC spectra showed a signal at δ 246.0 ppm that was assigned to the imine (C=N-) nitrogen. The signal at δ 26.2 ppm was assigned to the amine (NH2) nitrogen. The signals at δ 112.8 and δ 114.1 ppm were due to the
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Published 14 Oct 2019

Targeted photoswitchable imaging of intracellular glutathione by a photochromic glycosheet sensor

  • Xianzhi Chai,
  • Hai-Hao Han,
  • Yi Zang,
  • Jia Li,
  • Xiao-Peng He,
  • Junji Zhang and
  • He Tian

Beilstein J. Org. Chem. 2019, 15, 2380–2389, doi:10.3762/bjoc.15.230

Graphical Abstract
  • the photochromic fluorescence reporter into GSH-responsive MnO2 nanosheets, a highly efficient photoswitchable hybrid biosensor is successfully presented with the demanded functionality for precise cell imaging. Results and Discussion Synthesis of dithienylethene fluorescence reporter (Glyco-DTE) The
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Published 07 Oct 2019

Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups

  • Xiaowei Li,
  • Xiaolin Shi,
  • Xiangqian Li and
  • Dayong Shi

Beilstein J. Org. Chem. 2019, 15, 2213–2270, doi:10.3762/bjoc.15.218

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Published 23 Sep 2019

Harnessing enzyme plasticity for the synthesis of oxygenated sesquiterpenoids

  • Melodi Demiray,
  • David J. Miller and
  • Rudolf K. Allemann

Beilstein J. Org. Chem. 2019, 15, 2184–2190, doi:10.3762/bjoc.15.215

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  • , the presence of an ethereal oxygen atom containing π-acid functionality alongside its inductive withdrawal effect has a profound effect on the carbocationic reactivity of the intermediates. Of course a fully comprehensive interpretation of these results, regarding potentially interesting aspects such
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Published 17 Sep 2019

An overview of the cycloaddition chemistry of fulvenes and emerging applications

  • Ellen Swan,
  • Kirsten Platts and
  • Anton Blencowe

Beilstein J. Org. Chem. 2019, 15, 2113–2132, doi:10.3762/bjoc.15.209

Graphical Abstract
  • function as 2π, 4π, 6π or 10π components (Table 2). This functionality is dependent both on the other reactant partner, and the electronic effects of the fulvene substituents [96][97][98][99][153][156]. As an example, in [4 + 2] cycloadditions, fulvenes will participate as 4π components (diene), provided
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Published 06 Sep 2019

Synthesis and anion binding properties of phthalimide-containing corona[6]arenes

  • Meng-Di Gu,
  • Yao Lu and
  • Mei-Xiang Wang

Beilstein J. Org. Chem. 2019, 15, 1976–1983, doi:10.3762/bjoc.15.193

Graphical Abstract
  • conformational structures to complex anions in the gas phase and in the solid state owing to the anion–π noncovalent interactions between anions and the tetrazine rings. The easy accessibility, cylindroid cavity and diverse functionality would engender phthalimide-containing functionalized O6-corona[3]arene[3
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Published 21 Aug 2019

The cyclopropylcarbinyl route to γ-silyl carbocations

  • Xavier Creary

Beilstein J. Org. Chem. 2019, 15, 1769–1780, doi:10.3762/bjoc.15.170

Graphical Abstract
  • borohydride reduction of the ester functionality of 63 gave a separable mixture of alcohols 64 and 65. The stereochemistry of the product 65 was established using nOe studies. Cyano to carbomethoxy conversion in 65 to give alcohol 66 was straightforward. Triflate derivatives 67 and 68 were prepared since
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Published 24 Jul 2019

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

  • Gagandeep Kour Reen,
  • Ashok Kumar and
  • Pratibha Sharma

Beilstein J. Org. Chem. 2019, 15, 1612–1704, doi:10.3762/bjoc.15.165

Graphical Abstract
  • performed a Cu(OAc)2-Et3N-mediated coupling reaction of α-azido ketones 115 with pyridinium ylides 114 using oxygen as a green oxidant (Scheme 40). The oxo-functionality present in α-azido ketones increased its acidity thus making it a good organic synthon. Optimization of the reaction conditions revealed
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Published 19 Jul 2019

Synthesis, enantioseparation and photophysical properties of planar-chiral pillar[5]arene derivatives bearing fluorophore fragments

  • Guojuan Li,
  • Chunying Fan,
  • Guo Cheng,
  • Wanhua Wu and
  • Cheng Yang

Beilstein J. Org. Chem. 2019, 15, 1601–1611, doi:10.3762/bjoc.15.164

Graphical Abstract
  • versatile functionality [9] in recent years. Pillar[5]arenes [10], are cyclic pentamers composed of 1,4-dialkoxybenzene units connected through methylene bridges at the para-position and have a unique symmetrical architecture with an overall cylindrical or pillar-like shape. By virtue of their rigid and
  • symmetrical structures, as well as highly tunable functionality, the studies on pillar[5]arenes have been developed rapidly in various areas, such as artificial transmembrane channels [11][12], molecular complexation [13][14] and nonporous adaptive crystals [15][16][17]. One of the features of pillar[5]arenes
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Published 18 Jul 2019
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