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Search for "phosphate" in Full Text gives 453 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Diversity-oriented synthesis of spirothiazolidinediones and their biological evaluation

  • Sambasivarao Kotha,
  • Gaddamedi Sreevani,
  • Lilya U. Dzhemileva,
  • Milyausha M. Yunusbaeva,
  • Usein M. Dzhemilev and
  • Vladimir A. D’yakonov

Beilstein J. Org. Chem. 2019, 15, 2774–2781, doi:10.3762/bjoc.15.269

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  • performed by staining cells with 7-AAD (7-aminoactinomycin D, Biolegend) in a similar manner as described in [62]. In brief, after treatment cells were harvested, washed 1–2 times with phosphate-buffered saline (PBS) and centrifuged at 400g for 5 minutes. Cell pellets were resuspended in 200 µL of flow
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Published 18 Nov 2019

Safe and highly efficient adaptation of potentially explosive azide chemistry involved in the synthesis of Tamiflu using continuous-flow technology

  • Cloudius R. Sagandira and
  • Paul Watts

Beilstein J. Org. Chem. 2019, 15, 2577–2589, doi:10.3762/bjoc.15.251

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  • use of a base in the DPPA procedure was unavoidable as the reaction did not proceed in its absence. This can be understood by considering the DPPA azidating mechanism. The reaction takes place in two discrete steps, the first being phosphate formation followed by azide displacement (Scheme 4) [24]. We
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Published 30 Oct 2019

α,ß-Didehydrosuberoylanilide hydroxamic acid (DDSAHA) as precursor and possible analogue of the anticancer drug SAHA

  • Shital K. Chattopadhyay,
  • Subhankar Ghosh,
  • Sarita Sarkar and
  • Kakali Bhadra

Beilstein J. Org. Chem. 2019, 15, 2524–2533, doi:10.3762/bjoc.15.245

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  • inhibition) values of SAHA, 11b, 11f, 11g for HeLa cells (cervical carcinoma) were calculated by MTT (1 mg/mL of the tetrazolium dye, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide dissolved in phosphate-buffered saline, pH 7.4) assay [34]. Cells without any drug treatment were considered as
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Published 24 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

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  • -penetrating wavelengths. Peptide nucleic acids (PNAs) [31] are synthetic nucleic acid analogues, in which nucleobases are linked to a repeating N-(2-aminoethyl)glycine polyamide backbone. The lack of phosphate groups provides them with both higher binding affinities to complementary DNA or RNA sequences and
  • the PNAs, UV–vis spectroscopy of 20 μM solutions in phosphate buffer (10 mM NaH2PO4, 150 mM NaCl, pH 7.4) confirmed that PNA incorporation did not significantly affect the photochromism (Figures S24, S20, S30 and S33, Supporting Information File 1). This verifies the integrity of the chromophores
  • -ortho-fluoroazobenze (oF4Azo) and 2.: hemithioindigo (HTI). Time-dependent conversion to the thermodynamically stable isomer of PNA12(oF4Azo) (3; green triangles) and PNA12(HTI) (4; red circles). 20 µM solutions of the corresponding compound in phosphate buffer (10 mM NaH2PO4, 150 mM NaCl, pH 7.4) were
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Published 22 Oct 2019

Small anion-assisted electrochemical potential splitting in a new series of bistriarylamine derivatives: organic mixed valency across a urea bridge and zwitterionization

  • Keishiro Tahara,
  • Tetsufumi Nakakita,
  • Alyona A. Starikova,
  • Takashi Ikeda,
  • Masaaki Abe and
  • Jun-ichi Kikuchi

Beilstein J. Org. Chem. 2019, 15, 2277–2286, doi:10.3762/bjoc.15.220

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  • characteristics and fabricating sophisticated molecular devices through supramolecular methods. Experimental Materials and general measurements All solvents and chemicals of reagent grade were used without purification except tetra-n-butylammonium phosphate (n-Bu4NPF6), which was recrystallized from methanol. 4
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Published 24 Sep 2019

1,2,3-Triazolium macrocycles in supramolecular chemistry

  • Mastaneh Safarnejad Shad,
  • Pulikkal Veettil Santhini and
  • Wim Dehaen

Beilstein J. Org. Chem. 2019, 15, 2142–2155, doi:10.3762/bjoc.15.211

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  • highest affinity of this receptor was for acetate (Ka = 1.5 × 105 M−1) and dihydrogen phosphate (Ka = 4.5 × 104 M−1). Because of the excellent properties of perylene diimide (PDI) as a chromophore, fluorophore, or redox center, this unit has become increasingly popular in the construction of
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Published 12 Sep 2019

α-Photooxygenation of chiral aldehydes with singlet oxygen

  • Dominika J. Walaszek,
  • Magdalena Jawiczuk,
  • Jakub Durka,
  • Olga Drapała and
  • Dorota Gryko

Beilstein J. Org. Chem. 2019, 15, 2076–2084, doi:10.3762/bjoc.15.205

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  • only small amounts of the desired product 6 (Table 1, entry 1), higher yields were obtained in the presence of imidazolidinone 16 and silyl ether (S)-17, 31% and 52%, respectively (Table 1, entries 2 and 3). The yield further increased to 59% upon the addition of phosphate buffer. The highest level of
  • synthesis (Table 1, entry 2), suggesting that the reaction conditions are not compatible with one another. The use of silyl ether (S)-17 instead of imidazolidinone 16 and phosphate buffer (pH 7) as an additive allowed to increase the yield of the ‘one-pot’ procedure to 30% (Table 2, entries 2 and 3
  • % ee [α]D20 −147.0 (c 0.6, CHCl3). Enantiomer R,R (syn-6) 99% ee, [α]D20 −104.0 (c 0.4, CHCl3). General procedure for α-photooxygenation with phosphate buffer solution To a 10 mL vial a solution of meso-tetraphenylporphyrin (H2TPP, 0.4 mg, 0.63 µmol, 0.25 mol %) in CCl4 (1 mL) and organocatalyst (S)-17
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Published 30 Aug 2019

Synthesis of 1-azaspiro[4.4]nonan-1-oxyls via intramolecular 1,3-dipolar cycloaddition

  • Yulia V. Khoroshunova,
  • Denis A. Morozov,
  • Andrey I. Taratayko,
  • Polina D. Gladkikh,
  • Yuri I. Glazachev and
  • Igor A. Kirilyuk

Beilstein J. Org. Chem. 2019, 15, 2036–2042, doi:10.3762/bjoc.15.200

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  • results lead us to the assumption that symmetric structures with bulky substituents at positions 3 and 4 should be favoured for achieving higher resistance to reduction. Structure of nitroxide 1. Kinetics of the reduction of nitroxides 1 and 12a–c (0.3 mM) with ascorbate (50 mM) in 50 mM phosphate-citrate
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Published 27 Aug 2019
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  • mevalonate-dependent biosynthesis pathway (MVA) localized in the cytoplasm as well as via the mevalonate-independent 1-deoxy-ᴅ-xylulose 5-phosphate/2-C-methyl-ᴅ-erythritol 4-phosphate metabolic pathway (DOXP/MEP) localized in plastids [5]. In the MVA pathway, which was first described in yeast and animals
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Published 14 Aug 2019

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

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  • study U-2 OS and MRC-5 cells (1·105 cells per well) were seeded on 35 mm glass bottom dishes for live-cell imaging (MatTek Corporation, USA) and left to adhere for 24 h. Then, the cells were washed with phosphate-buffered saline (PBS) and incubated with compound 5 or dansyl amide fluorophore (0.1–2.0 µM
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Published 13 Aug 2019

N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds

  • Iwona E. Głowacka,
  • Aleksandra Trocha,
  • Andrzej E. Wróblewski and
  • Dorota G. Piotrowska

Beilstein J. Org. Chem. 2019, 15, 1722–1757, doi:10.3762/bjoc.15.168

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  • analogue SG-14 (2S,3S)-84 in inhibiting hSphK2. Sphingosine-1-phosphate (S1P) analogues (2S,3R)-89a and (2S,3R)-89b with 1,4- and 1,3-disubstituted benzene rings incorporated into the alkyl chain were obtained from aziridine ketones (2S,1'R)-90a and (2S,1'R)-90b (Scheme 23) readily prepared using Weinreb
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Published 23 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

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Published 19 Jul 2019

Molecular basis for the plasticity of aromatic prenyltransferases in hapalindole biosynthesis

  • Takayoshi Awakawa and
  • Ikuro Abe

Beilstein J. Org. Chem. 2019, 15, 1545–1551, doi:10.3762/bjoc.15.157

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  • structures. The indole of HU, W117, and Y168 formed a cation shield [27][28], which stabilizes the cation intermediate after the removal of the phosphate from DMAPP in the HU structure, and Y225 was substituted with Y168 in the HA structure (Figure 5). The orientation of W117 changed in accordance with the
  • other enzymes. In fact, the position of the α-phosphate shifts between the Mg2+-free and -bound structures in AmbP1 and between the HU and HA structures in AmbP3, which alters the locations of the substrates in the enzyme. In the AmbP3 structures, Y225 plays an important role to form a cation shield in
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Published 11 Jul 2019

Complexation of a guanidinium-modified calixarene with diverse dyes and investigation of the corresponding photophysical response

  • Yu-Ying Wang,
  • Yong Kong,
  • Zhe Zheng,
  • Wen-Chao Geng,
  • Zi-Yi Zhao,
  • Hongwei Sun and
  • Dong-Sheng Guo

Beilstein J. Org. Chem. 2019, 15, 1394–1406, doi:10.3762/bjoc.15.139

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  • fluorescence enhancement. Herein, the phosphate derivative of TPE, P-TPE, was employed as a model guest to examine the complexation behavior of GC5A with AIEgens. As shown in Figure 2a, a dramatic fluorescence enhancement was observed upon complexation with GC5A. This result is in good accordance with the
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Published 25 Jun 2019

Selenophene-containing heterotriacenes by a C–Se coupling/cyclization reaction

  • Pierre-Olivier Schwartz,
  • Sebastian Förtsch,
  • Astrid Vogt,
  • Elena Mena-Osteritz and
  • Peter Bäuerle

Beilstein J. Org. Chem. 2019, 15, 1379–1393, doi:10.3762/bjoc.15.138

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  • B3LYP and CAMB3LYP functional and 6-31++(d,p) basis-set [56]. Materials Iodine, zinc(II) chloride, copper(II) chloride, potassium hydroxide, chlorotrimethylsilane, copper(I) iodide, and potassium phosphate were purchased from Merck. Diisopropylamine, bis(dibenzylideneacetone)palladium(0
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Published 24 Jun 2019

Enantioselective Diels–Alder reaction of anthracene by chiral tritylium catalysis

  • Qichao Zhang,
  • Jian Lv and
  • Sanzhong Luo

Beilstein J. Org. Chem. 2019, 15, 1304–1312, doi:10.3762/bjoc.15.129

Graphical Abstract
  • of a highly active carbocation Lewis acid catalyst. The stereocontrol potential of the chiral tritylium ion pair was demonstrated by its application in an enantioselective Diels–Alder reaction of anthracene. Keywords: anthracene; carbocation catalysis; Diels–Alder reaction; Fe(III)-based phosphate
  • , the enantioselectivity was low in most cases. In addition, the synthetic efforts to access these chiral cations were generally non-trivial which limited their further development. Recently, we developed a chiral ion-pair strategy for asymmetric carbocation catalysis, with chiral trityl phosphate as
  • (Scheme 1b). In our further explorations, we noticed that the dissociation of trityl phosphate was generally sluggish, thus limiting its applicability. To expand its utility, we report herein a metal-complexed phosphate anion for chiral carbocation catalysis. Weakly coordinating anions [22][23] have been
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Published 14 Jun 2019

Synthesis of aryl cyclopropyl sulfides through copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acid

  • Emeline Benoit,
  • Ahmed Fnaiche and
  • Alexandre Gagnon

Beilstein J. Org. Chem. 2019, 15, 1162–1171, doi:10.3762/bjoc.15.113

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  • tolerated, giving a comparable yield as the "standard conditions" (Table 1, entry 8). While changing the inorganic base to potassium phosphate tribasic or potassium carbonate gave yields below 75%, we found that cesium carbonate provided a net increase in the yield of the reaction (Table 1, entry 9
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Published 27 May 2019

Electrophilic oligodeoxynucleotide synthesis using dM-Dmoc for amino protection

  • Shahien Shahsavari,
  • Dhananjani N. A. M. Eriyagama,
  • Bhaskar Halami,
  • Vagarshak Begoyan,
  • Marina Tanasova,
  • Jinsen Chen and
  • Shiyue Fang

Beilstein J. Org. Chem. 2019, 15, 1116–1128, doi:10.3762/bjoc.15.108

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  • removed with an acid in each synthetic cycle. The exo-amino groups of nucleosides dA, dC and dG are protected with acyl groups, the nascent ODN is anchored to a solid support via a base- or nucleophile-cleavable linker, and in the most widely used phosphoramidite technology the phosphate groups are
  • temperature briefly. This removed the β-cyanoethyl phosphate protecting groups to give 32. HPLC analysis of the DBU solution did not found any ODN that was cleaved prematurely – an observation consistent with the slow rate of cleavage of succinyl-anchored ODNs from solid support under similar conditions [50
  • equal portions. One portion was gently shaken in a solution of DBU/CH3CN (1:9, v/v, 1 mL) at rt for 15 min. The supernatant was removed with a pipette, and the CPG was washed with CH3CN (1 mL × 5). This removed the 2-cyanoethyl groups on the phosphate groups. To the CPG, aqueous NaIO4 (0.4 M, 1 mL) was
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Published 20 May 2019

Heck- and Suzuki-coupling approaches to novel hydroquinone inhibitors of calcium ATPase

  • Robert J. Kempton,
  • Taylor A. Kidd-Kautz,
  • Soizic Laurenceau and
  • Stefan Paula

Beilstein J. Org. Chem. 2019, 15, 971–975, doi:10.3762/bjoc.15.94

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  • , followed by addition of bromide 5a, potassium phosphate and PdCl2(dppf)2 in DMF at 85 °C for 3.5 h gave the coupled product 10 in 47–63% yields (Scheme 3). In contrast to the case of the Heck coupling products (6 and 8, Scheme 2), nitrile 10 underwent facile reduction with lithium aluminium hydride. The
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Published 24 Apr 2019

Towards the preparation of synthetic outer membrane vesicle models with micromolar affinity to wheat germ agglutinin using a dialkyl thioglycoside

  • Dimitri Fayolle,
  • Nathalie Berthet,
  • Bastien Doumeche,
  • Olivier Renaudet,
  • Peter Strazewski and
  • Michele Fiore

Beilstein J. Org. Chem. 2019, 15, 937–946, doi:10.3762/bjoc.15.90

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  • , bearing one or two N-acetyl glucosamine moieties are capable to bind strongly to the lectin WGA. Experimental Materials and methods Myristoyl chloride was from TCI-Europe (Antwerp, Belgium) and used without further purification. 1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphate (POPC) was from Avanti Polar
  • color was developed using OPD (100 μL per well, 0.4 mg mL−1 in 0.05 M phosphate-citrate buffer) and urea hydrogen peroxide (0.4 mg mL−1). The reaction was stopped after 10 min by adding H2SO4 (30% v/v, 50 μL per well) and the absorbance was measured at 490 nm. The percentage of inhibition was determined
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Published 17 Apr 2019

Azologization of serotonin 5-HT3 receptor antagonists

  • Karin Rustler,
  • Galyna Maleeva,
  • Piotr Bregestovski and
  • Burkhard König

Beilstein J. Org. Chem. 2019, 15, 780–788, doi:10.3762/bjoc.15.74

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  • performed in DMSO and depending on their solubility in phosphate buffer + 0.1% DMSO (16a–d) by UV–vis absorption spectroscopy. The compounds were dissolved at 50 µM in the respective solvent and irradiated with the indicated wavelengths to generate a substantial amount of their cis-isomer. This process can
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Published 25 Mar 2019

Tuning the stability of alkoxyisopropyl protection groups

  • Zehong Liang,
  • Henna Koivikko,
  • Mikko Oivanen and
  • Petri Heinonen

Beilstein J. Org. Chem. 2019, 15, 746–751, doi:10.3762/bjoc.15.70

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  • , d: R = isopropyl, e: R = CH2CF3. Proposed acetal hydrolysis pathways. Half-lives of 5’-acetal (4a–e) and 3’-acetal-protected (7a,c–e) 2’-deoxythymidines, and 2’-deoxy-3’-O-propen-2-ylthymidine (8b) in acetate (pH 4.94), citrate (pH 5.61) and phosphate (pH 6.82) buffers at 25.0 °C. The ionic strength
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Published 21 Mar 2019

Cyclopropene derivatives of aminosugars for metabolic glycoengineering

  • Jessica Hassenrück and
  • Valentin Wittmann

Beilstein J. Org. Chem. 2019, 15, 584–601, doi:10.3762/bjoc.15.54

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  • reaction: In a polypropylene vial, the sugar derivatives ManNCp(H2), ManNCyc(H2) and ManNCyoc(H2), respectively, were dissolved in phosphate buffer (100 mM, pH 7.16) to a final concentration of 0.1 M. Sodium pyruvate (15 equiv.) and sialic acid aldolase (a spatula tip) were added. After stirring for 17
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Published 04 Mar 2019

Back to the future: Why we need enzymology to build a synthetic metabolism of the future

  • Tobias J. Erb

Beilstein J. Org. Chem. 2019, 15, 551–557, doi:10.3762/bjoc.15.49

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  • into the three-carbon compound dihydroxyacetone phosphate [24]. In addition to that, several alternative photorespiration, methanol assimilation, as well as glycolytic pathways of levels 3 and 4 were developed that are supposedly more carbon and energy efficient compared to their naturally evolved
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Published 26 Feb 2019

Synthesis and fluorescent properties of N(9)-alkylated 2-amino-6-triazolylpurines and 7-deazapurines

  • Andrejs Šišuļins,
  • Jonas Bucevičius,
  • Yu-Ting Tseng,
  • Irina Novosjolova,
  • Kaspars Traskovskis,
  • Ērika Bizdēna,
  • Huan-Tsung Chang,
  • Sigitas Tumkevičius and
  • Māris Turks

Beilstein J. Org. Chem. 2019, 15, 474–489, doi:10.3762/bjoc.15.41

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  • were replaced with 500 μL of cell culture medium containing the compound, and then further cultured for an additional 1 h. Those cells were washed twice with 1× PBS and fixed to the membrane using 4% paraformaldehyde in 5.0 mM sodium phosphate buffer (pH 7.4; 1.0 mL) for 10 min. The fluorescence images
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Published 15 Feb 2019
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