A smart deoxyribozyme-based fluorescent sensor for in vitro detection of androgen receptor mRNA

• Ekaterina A. Bryushkova,
• Erik R. Gandalipov and
• Julia V. Nuzhina

Beilstein J. Org. Chem. 2020, 16, 1135–1141, doi:10.3762/bjoc.16.100

• electrode, covered by immobilizing enzyme glucose oxidase, for the detection of glucose [1]. A biosensor means a small molecular device that traditionally consists of a bioreceptor (enzyme, cell, aptamer, oligonucleotide, antibody, and other) for the specific recognition of the target molecule and a

A cyclopeptide and three oligomycin-class polyketides produced by an underexplored actinomycete of the genus Pseudosporangium

• Shun Saito,
• Kota Atsumi,
• Tao Zhou,
• Keisuke Fukaya,
• Daisuke Urabe,
• Naoya Oku,
• Md. Rokon Ul Karim,
• Hisayuki Komaki and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 1100–1110, doi:10.3762/bjoc.16.97

• strain 3-44-a(19)T (AB302183). Fermentation Strain RD062863 growing on double-diluted ISP2 agar medium consisting of yeast extract 0.2%, malt extract 0.5%, glucose 0.2%, and agar 2% (pH 7.3) was inoculated into test tubes (inner diameter, 15 mm; length 16.5 cm) each containing 5 mL of YG seed medium

• consisting of glucose 1% and yeast extract 1% (pH 7.0). The tubes were placed in a shaker TC-500R (Takasaki Scientific Instruments Corp.) (260 strokes/min) at 28 °C for 4 days. Then, the seed culture (1 mL) was transferred into 500 mL Erlenmeyer flasks each containing 100 mL of modified A3M production medium

• consisting of glucose 0.5%, glycerol 2%, soluble starch 2%, Pharmamedia (Traders Protein) 1.5%, dry yeast (Kamaishi Hamayuri Yeast, Nihon Tensai Seito Co., Ltd.) 0.3%. The pH of the medium was adjusted to 7.0 before sterilization. The inoculated flasks were placed on a rotary shaker TB98 (Takasaki Scientific

Synthesis of new asparagine-based glycopeptides for future scanning tunneling microscopy investigations

• Laura Sršan and
• Thomas Ziegler

Beilstein J. Org. Chem. 2020, 16, 888–894, doi:10.3762/bjoc.16.80

• -linked structures are N-acetylglycosylamines, glucose, galactose, mannose, cellobiose, lactose, and maltose [19]. Therefore, we intended to prepare glycopeptide structures containing these sugars in a stepwise way, up to tripeptides. An orthogonal Fmoc/t-Bu protecting group strategy was chosen along with

• synthesis of a series of new glycopeptides containing asparagine, tryptophane, alanine, and phenylalanine linked to various saccharides, such as glucose, galactose, mannose, cellobiose, lactose, and maltose. We further compared two common peptide coupling procedures that use HBTU and HATU, respectively. We

Synthesis of disparlure and monachalure enantiomers from 2,3-butanediacetals

• Adam Drop,
• Hubert Wojtasek and
• Bożena Frąckowiak-Wojtasek

Beilstein J. Org. Chem. 2020, 16, 616–620, doi:10.3762/bjoc.16.57

• ensure the required configuration of the asymmetric centers determining the biological activity of this compound. They include the use of naturally occurring chiral substrates, such as ʟ-glutamic acid [13], ʟ-tartaric acid [14][15][16], ᴅ-glucose [17], and sorbitol [18] as starting materials, as well as

Two antibacterial and PPARα/γ-agonistic unsaturated keto fatty acids from a coral-associated actinomycete of the genus Micrococcus

• Amit Raj Sharma,
• Enjuro Harunari,
• Naoya Oku,
• Nobuyasu Matsuura,
• Agus Trianto and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 297–304, doi:10.3762/bjoc.16.29

• incubated at 30 °C on a rotary shaker at 200 rpm for two days. Three mL each of the seed culture were inoculated into 29 500 mL K-1 flasks containing 100 mL of A16 production medium, which consisted of glucose 2%, Pharmamedia (Traders Protein, Memphis, TN, USA) 1%, CaCO3 0.5%, Diaion HP-20 (Mitsubishi

Synthesis of C-glycosyl phosphonate derivatives of 4-amino-4-deoxy-α-ʟ-arabinose

• Lukáš Kerner and
• Paul Kosma

Beilstein J. Org. Chem. 2020, 16, 9–14, doi:10.3762/bjoc.16.2

• ). Conversion of benzylated reducing sugars, such as glucose [15], N-acetyl-ᴅ-glucosamine [16], and galactose [17], into the corresponding C-glycosyl phosponates using a Wittig reaction with methylenetriphenylphosphorane furnished the respective glycoenitols, which were then subjected to mercuriocyclization

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

• , SnCl4 and Sn(OTf)2 might have formed a coordination bond with the carbonyl oxygen atom of the C-5 NHAc group and the O-6 position of the glucose glucopyranosyl ring. In turn, this retarded the ring-opening reaction. The anchimeric participation of the NHAc group in stabilizing the axial conformation of

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

• elucidation Gibellula sp. was cultivated in liquid yeast, malt, and glucose (YMG) medium and extracted as described in the Experimental section. The extracts were purified by HPLC to give pigmentosin A (1) and pigmentosin B (2). Using a similar procedure, compounds 3–6 were obtained from the liquid culture of

• medium, and incubated at 23 °C on a shaker at 140 rpm. The free glucose content of each fermented broth was tentatively monitored using Bayer Diastix Harnzuckerstreifen. After the glucose was depleted, the incubation was prolonged for half of the time each strain had taken for glucose consumption, and

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

• KJMT.FP.4.3 cultured on PDA agar was inoculated into 500 mL K-1 flasks each containing V22 seed medium consisting of soluble starch 1%, glucose 0.5%, NZ-case (Sigma-Aldrich, Co., LLC.) 0.3%, yeast extract (Kyokuto Pharmaceutical Industrial, Co., Ltd.) 0.2%, Tryptone (Difco Laboratories) 0.5%, K2HPO4 0.1

• %, MgSO4·7H2O 0.05%, and CaCO3 0.3% (pH 7.0). The flasks were shaken at 30 °C for 4 days on a rotary shaker (200 rpm). The seed culture (3 mL) was transferred into 500 mL K-1 flasks each containing 100 mL of A3M production medium (pH 7.0) consisting of 2.0% soluble starch, 0.5% glucose, 2.0% glycerol, 0.3

Preparation of anthracene-based tetraperimidine hexafluorophosphate and selective recognition of chromium(III) ions

• Qing-Xiang Liu,
• Feng Yang,
• Zhi-Xiang Zhao,
• Shao-Cong Yu and
• Yue Ding

Beilstein J. Org. Chem. 2019, 15, 2847–2855, doi:10.3762/bjoc.15.278

• of Cr3+ ions occupies an important position. Chromium(III) is an essential microelement for humans and animals, and it plays an important role in glucose and lipid metabolism in the body [9][10]. The deficiency of chromium(III) in the human body leads to various diseases, such as diabetes as well as

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

• labeling, labeling solutions were checked by UPLC. The external solution was (in mM): 140 NaCl, 2.8 KCl, 2 CaCl2, 2 MgCl2, 10 HEPES, 12 glucose (pH 7.3 with NaOH). Compound 1 (0.05 mM) was dissolved in external solution and sonicated for 5 min. HEK293 cells with green fluorescence were chosen for recording

• KCl, 1.25 NaH2PO4, 7 MgCl2, 0.5 CaCl2, 26 NaHCO3, 10 glucose, 100 sucrose, 3 sodium pyruvate, 1.3 sodium ascorbate equilibrated with 95% O2/5% CO2 (pH 7.3–7.4). The brain slices were then incubated for 15 min at 33 °C in artificial cerebrospinal fluid (ACSF, mM: 125 NaCl, 2.5 KCl, 1.25 NaH2PO4, 1

• MgCl2, 2 CaCl2, 26 NaHCO3, 10 glucose, 3 sodium pyruvate, 1.3 sodium ascorbate; 95% O2/5% CO2, pH 7.3–7.4) and held at room temperature. Brain slices were then transferred to the recording chamber of a BX-61 microscope (Olympus, PennValley, PA, USA) and superfused with ACSF at room temperature. Medial

Skeletocutins M–Q: biologically active compounds from the fruiting bodies of the basidiomycete Skeletocutis sp. collected in Africa

• Tian Cheng,
• Clara Chepkirui,
• Cony Decock,
• Josphat C. Matasyoh and
• Marc Stadler

Beilstein J. Org. Chem. 2019, 15, 2782–2789, doi:10.3762/bjoc.15.270

• standard turbidity in casein-peptone soymeal-peptone (CASO) medium containing 4% glucose at pH 7.0 for biofilm formation. Methanol was used as negative control, while tetracycline was used as positive control. All experiments were made in triplicates. Nematicidal activity assay The nematicidal activity of

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

• , the disaccharide donor 16 may be prepared from monosaccharide acceptor 15 and donor 14. The monosaccharide building blocks can be prepared from commercially available ᴅ-glucose, ᴅ-galactose, ᴅ-glucosamine hydrochloride and ʟ-rhamnose through rational protecting group manipulations (Figure 2

Indium-mediated C-allylation of melibiose

• Christian Denner,
• Manuel Gintner,
• Hanspeter Kählig and
• Walther Schmid

Beilstein J. Org. Chem. 2019, 15, 2458–2464, doi:10.3762/bjoc.15.238

• glucose moiety allowing most spatial freedom for the elongation reaction at the anomeric position of the reducing end of the disaccharide (Scheme 1). First, we investigated different reaction parameters such as the metal species, the solvent system, the activation by sonication as well as the temperature

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

• demonstrated better selective Cl− ion transport activity as compared to the pseudodipeptide 1. To the best of our knowledge, this is the first report on the formation of oxazolone peptides from TSFAA that induces a γ-turn and demonstrate ion transport activity. Results and Discussion At first, ᴅ-glucose was

Isolation and biosynthesis of an unsaturated fatty acid with unusual methylation pattern from a coral-associated bacterium Microbulbifer sp.

• Amit Raj Sharma,
• Enjuro Harunari,
• Tao Zhou,
• Agus Trianto and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2019, 15, 2327–2332, doi:10.3762/bjoc.15.225

• mL of marine broth 2216 (Difco) as a seed culture. The seed culture was incubated at 30 °C on a rotary shaker at 200 rpm for 2 days. Three mL of seed culture was inoculated into twenty-five 500 mL K-1 flasks each containing 100 mL of A11M production medium, which consists of glucose 0.2%, soluble

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

• ) and, the cells were incubated for another 24, 48 and 72 h. Next, the medium was removed and the cells were incubated with 5 µL of WST-1 dissolved in 100 µL of high glucose DMEM without phenol red with 10% FBS for 2 h. Then, the absorbance was measured. Cells incubated with a vehicle (DMSO) in medium

Synthesis of a [6]rotaxane with singly threaded γ-cyclodextrins as a single stereoisomer

• Jason Yin Hei Man and
• Ho Yu Au-Yeung

Beilstein J. Org. Chem. 2019, 15, 1829–1837, doi:10.3762/bjoc.15.177

• -CD), seven (β-CD) and eight (γ-CD) glucose units are important molecular hosts that show binding to a wide range of compounds and find applications in different fields including food and pharmaceutical industries [1][2][3][4][5]. CDs are of cone shape with two different openings: a narrower primary

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

• protocol also provided a concise route for the synthesis of the antiulcer drug zolimidine in 95% yield. A three-component coupling reaction (3-CCR) for the synthesis of N-fused pyridines was reported by Balijapalli and Iyer [40]. The reaction was catalyzed by CuO/CuAl2O4 and ᴅ-glucose. The reaction had

• been tried with various Cu(I)- and Cu(II)-based catalysts but the use of a mixed nano-CuO/CuAl2O4 and ᴅ-glucose system has resulted in appreciable yields. This three-component one-pot reaction involved 2-AP, phenylacetylene and substituted benzaldehydes as the starting substrates (Scheme 34). The

Synthesis of 9-O-arylated berberines via copper-catalyzed C_Ar–O coupling reactions

• Qiaoqiao Teng,
• Xinhui Zhu,
• Qianqian Guo,
• Weihua Jiang,
• Jiang Liu and
• Qi Meng

Beilstein J. Org. Chem. 2019, 15, 1575–1580, doi:10.3762/bjoc.15.161

• elaborate motifs such as heterocycles [10][11][12], glucose [13], nitric oxide [14], and the multidrug-resistance pump inhibitor 5-nitro-2-phenylindole (INF55) [15] have been covalently attached to BBR, further widening its pharmacological spectrum. Aromatic rings are another family of substituents having

2,3-Dibutoxynaphthalene-based tetralactam macrocycles for recognizing precious metal chloride complexes

• Li-Li Wang,
• Yi-Kuan Tu,
• Huan Yao and
• Wei Jiang

Beilstein J. Org. Chem. 2019, 15, 1460–1467, doi:10.3762/bjoc.15.146

• recognition of glucose in water [21][22][23]. However, the aromatic sidewalls of these tetralactams are currently limited to benzene, anthracene and their derivatives (Scheme 1). The extension of the sidewalls to naphthalenes should be an important supplement to the previous works, and may even lead to

Anomeric sugar boronic acid analogues as potential agents for boron neutron capture therapy

• Daniela Imperio,
• Erika Del Grosso,
• Silvia Fallarini,
• Grazia Lombardi and
• Luigi Panza

Beilstein J. Org. Chem. 2019, 15, 1355–1359, doi:10.3762/bjoc.15.135

• boron-containing carbohydrate derivatives for BNCT has received special attention because of the sugar-preferential uptake by tumor cells [3]. Tumor cells perform glycolysis at a faster rate than their noncancerous tissue counterparts, so increasing the glucose consumption with respect to healthy cells

• . Galactose and fructose also allow tumor growth in the absence of glucose. Boronic acid derivatives have gained interest in the last years in different fields such as the development of enzyme inhibitors, drug delivery polymers, saccharide sensors and as boron carriers for BNCT, e.g., amino acid derivatives

Genomics-inspired discovery of massiliachelin, an agrochelin epimer from Massilia sp. NR 4-1

• Jan Diettrich,
• Hirokazu Kage and
• Markus Nett

Beilstein J. Org. Chem. 2019, 15, 1298–1303, doi:10.3762/bjoc.15.128

• (0.5 g/L yeast extract, 0.5 g/L proteose peptone, 0.5 g/L casamino acids, 0.5 g/L glucose, 0.5 g/L soluble starch, 0.3 g/L sodium pyruvate, 0.3 g/L K2HPO4 and 0.05 g/L MgSO4·7H2O, pH 7.2). The cultures were shaken at 160 rpm and 30 °C. After seven days of cultivation the fermentation broth was

Steroid diversification by multicomponent reactions

• Leslie Reguera,
• Cecilia I. Attorresi,
• Javier A. Ramírez and
• Daniel G. Rivera

Beilstein J. Org. Chem. 2019, 15, 1236–1256, doi:10.3762/bjoc.15.121

• conjugation [62][63]. Cytotoxic spirostan saponins were chosen as model compounds for the preparation of Ugi-derived analogues, such as 55 and 56 suitable for biological evaluation [62]. Besides the glucose unit, other trisaccharidic moieties (e.g., β-chacotrioside) could also be conjugated to functionalized

Molecular recognition using tetralactam macrocycles with parallel aromatic sidewalls

• Dong-Hao Li and
• Bradley D. Smith

Beilstein J. Org. Chem. 2019, 15, 1086–1095, doi:10.3762/bjoc.15.105

• -Bu). a) Chemical structure of β-D-glucopyranose and the solid-state structure of its complexes with macrocycle B (X = CH). b) Schematic view of tetralactam B encapsulating glucose (R = O) or glucosammonium (R = NH2+) with stabilizing secondary interactions provided by back-folding of a peripherally