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

• transform into a green-blue chromophore in the presence of peroxides or redox-active metal ions under acidic conditions, creating a potential detection method for such entities [29]. Additionally, the same structure was used for the preparation of a benzo-1,4-thiazine-based cyanine chromophore, which showed

Synthesis of N-phenyl- and N-thiazolyl-1H-indazoles by copper-catalyzed intramolecular N-arylation of ortho-chlorinated arylhydrazones

• Yara Cristina Marchioro Barbosa,
• Guilherme Caneppele Paveglio,
• Claudio Martin Pereira de Pereira,
• Sidnei Moura,
• Cristiane Storck Schwalm,
• Gleison Antonio Casagrande and
• Lucas Pizzuti

Beilstein J. Org. Chem. 2022, 18, 1079–1087, doi:10.3762/bjoc.18.110

• resealable screw-cap Schlenk flask (≈10 mL volume) in the presence of a Teflon-coated magnetic stirring bar. TLC analyses were performed with Al plates covered with silica gel (SiliCycle, F254) and visualized by UV detection. Silica gel (Vetec, 0.063–0.200 mm, 70–230 mesh) was used for column chromatography

New azodyrecins identified by a genome mining-directed reactivity-based screening

• Atina Rizkiya Choirunnisa,
• Kuga Arima,
• Yo Abe,
• Noritaka Kagaya,
• Kei Kudo,
• Hikaru Suenaga,
• Junko Hashimoto,
• Manabu Fujie,
• Noriyuki Satoh,
• Kazuo Shin-ya,
• Kenichi Matsuda and
• Toshiyuki Wakimoto

Beilstein J. Org. Chem. 2022, 18, 1017–1025, doi:10.3762/bjoc.18.102

• natural products, despite their notable biological activities. Reactivity-based screening is an emerging strategy in natural products discovery, in which chemical probes are used for the specific detection of the unique functionality of interest in crude metabolites [5][6]. The reactions usually

• macrozamin [4]. Although the N2H4 generation is an advantageous reactivity of an azoxy group, to the best of our knowledge, it has not been applied for the detection of azoxy bonds in the context of natural products discovery. The azoxy bond is biosynthesized by two distinct mechanisms. The first is the

The stereochemical course of 2-methylisoborneol biosynthesis

• Binbin Gu,
• Anwei Hou and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2022, 18, 818–824, doi:10.3762/bjoc.18.82

• the genes for the biosynthesis of 1 are present in about half of the species [28], which is reflected by the frequent detection of 1 among the volatiles emitted by a large number of streptomycetes and closely related bacteria [3][4][5][6][7]. A series of side products of the 2MIBS has been identified

Thiophene/selenophene-based S-shaped double helicenes: regioselective synthesis and structures

• Mengjie Wang,
• Lanping Dang,
• Wan Xu,
• Zhiying Ma,
• Liuliu Shao,
• Guangxia Wang,
• Chunli Li and
• Hua Wang

Beilstein J. Org. Chem. 2022, 18, 809–817, doi:10.3762/bjoc.18.81

• ]. Column chromatography was carried out on silica gel (300–400 mesh). Analytical thin-layer chromatography was performed on glass plates of silica gel GF-254 with detection by UV. Standard techniques for synthesis under inert atmosphere and Schlenk glassware equipped with an 8 mm PTFE vacuum stopcock, were

Synthesis of bis-spirocyclic derivatives of 3-azabicyclo[3.1.0]hexane via cyclopropene cycloadditions to the stable azomethine ylide derived from Ruhemann's purple

• Alexander S. Filatov,
• Olesya V. Khoroshilova,
• Anna G. Larina,
• Vitali M. Boitsov and
• Alexander V. Stepakov

Beilstein J. Org. Chem. 2022, 18, 769–780, doi:10.3762/bjoc.18.77

• observed signals were at the limit of detection and whether they actually correspond to a minor diastereomer could not be ascertained unambiguously. The major product 4 was purified by recrystallization of the crude mixture from MeOH and obtained in 62% yield. The structure and relative configuration of

Terpenoids from Glechoma hederacea var. longituba and their biological activities

• Dong Hyun Kim,
• Song Lim Ham,
• Zahra Khan,
• Sun Yeou Kim,
• Sang Un Choi,
• Chung Sub Kim and
• Kang Ro Lee

Beilstein J. Org. Chem. 2022, 18, 555–566, doi:10.3762/bjoc.18.58

• . The monosaccharide of 5 was detected at 13.8 min, the same detection time (13.8 min) as ᴅ-glucopyranoside. LC–MS analysis was perfomed under the following conditions: flow rate 0.7 mL/min; 25% MeCN with 0.1% formic acid, column, Kinetex C18 column (250 mm × 4.6 mm, 5 µm, Phenomenex). Sugar analysis

• ), the reaction mixture was allowed to react again at 60 °C for 2 h. The reactant was suspended in distilled H2O (1 mL) and then partitioned with n-hexane (1 mL). The n-hexane soluble layer was analyzed using GC–MS analysis. All monosaccharides were detected at 11.3 min, the same detection time (11.3 min

Site-selective reactions mediated by molecular containers

• Rui Wang and
• Yang Yu

Beilstein J. Org. Chem. 2022, 18, 309–324, doi:10.3762/bjoc.18.35

• increasing DMSO concentration, without the detection of any monohydrolyzed product. This work further demonstrated the striking ability of the water-soluble cavitand to mediate site-selective reactions. Conclusion To summarize, we have reviewed various site-selective reactions mediated by molecular

Recent developments and trends in the iron- and cobalt-catalyzed Sonogashira reactions

• Surendran Amrutha,
• Sankaran Radhika and
• Gopinathan Anilkumar

Beilstein J. Org. Chem. 2022, 18, 262–285, doi:10.3762/bjoc.18.31

• for the effective Sonogashira coupling under aqueous conditions (Scheme 3) [22]. The coupling reaction was catalyzed by the nanoparticles in water between room temperature and 45 °C. Notably, the amount of Pd was below the detection limit. The reaction done in the presence of 1000 ppm of Pd ligated

Anomeric 1,2,3-triazole-linked sialic acid derivatives show selective inhibition towards a bacterial neuraminidase over a trypanosome trans-sialidase

• Peterson de Andrade,
• Sanaz Ahmadipour and
• Robert A. Field

Beilstein J. Org. Chem. 2022, 18, 208–216, doi:10.3762/bjoc.18.24

• both enzymes (Figure 3A) (and TcTS transferase activity in the presence of an acceptor substrate, such as lactose – Figure 3B) by releasing the fluorophore 4-methylumbelliferone (MU) for detection upon cleavage of the substrate 2'-(4-methylumbelliferyl) α-ᴅ-N-acetylneuraminic acid (MUNANA). Compounds

The role of chemistry in the success of oligonucleotides as therapeutics

• Pawan Kumar and
• Tom Brown

Beilstein J. Org. Chem. 2022, 18, 197–199, doi:10.3762/bjoc.18.22

• oligonucleotide primers and probes for use in diagnostic testing kits for the detection of COVID-19 for tackling the pandemic. With this thematic issue, we express our sincere gratitude to all the scientists for their ground-breaking work to bring oligonucleotide therapeutics to the bedside. We also express our

Study on the interactions between melamine-cored Schiff bases with cucurbit[n]urils of different sizes and its application in detecting silver ions

• Jun-Xian Gou,
• Yang Luo,
• Xi-Nan Yang,
• Wei Zhang,
• Ji-Hong Lu,
• Zhu Tao and
• Xin Xiao

Beilstein J. Org. Chem. 2021, 17, 2950–2958, doi:10.3762/bjoc.17.204

• host–guest interactions. Among them, Q[7]-TBT is selected as a UV detector for the detection of silver ions (Ag+). This work makes full use of the characteristics of each cucurbituril and melamine-cored Schiff base to construct a series of complexes and these are applied to metal detection. Keywords

• to yield different metal-organic frameworks [6][7][8][9][10][11], but also can be used as analytical reagents for the detection of different organic and inorganic substances [12][13][14]. Among the various central molecules for the synthesis of Schiff bases, melamine (2,4,6-triamino-s-triazine) has

• supermolecule polymer with TBT due to its larger cavity. Since Q[7] and TBT form a host–guest complex, the carboxyl group at the end of TBT and the carbonyl group of the Q[7] still have a strong ability to coordinate with metals. Therefore, Q[7]-TBT is selected for the detection of silver ions (Ag+) [32][33

First total synthesis of hoshinoamide A

• Haipin Zhou,
• Zihan Rui,
• Yiming Yang,
• Shengtao Xu,
• Yutian Shao and
• Long Liu

Beilstein J. Org. Chem. 2021, 17, 2924–2931, doi:10.3762/bjoc.17.201

• % CH3CN/H2O and 0.1% TFA over 40 min were applied at a flow rate of 1.0 mL/min and detection at 220 nm. Method B: Linear gradient of 10–90–90–10% CH3CN/H2O and 0.1% TFA over 10 min (10–90 vol % MeCN over 6 min, 90–90 vol % over 3 min, 90–10 vol % MeCN over 1 min) were applied at a flow rate of 1.0 mL/min

• and detection at 220 nm. Preparative reverse-phase HPLC was performed by using Thermo Scientific Ultimate 3000 equipped with a Thermo Hypersil Gold (5 µm, 150 × 21.2 mm) column adpoting the following buffer systems: A: 0.1% TFA in water. B: 0.1% TFA in MeCN using a 10–90–90–10 vol % MeCN gradient (10

Biological properties and conformational studies of amphiphilic Pd(II) and Ni(II) complexes bearing functionalized aroylaminocarbo-N-thioylpyrrolinate units

• Samet Poyraz,
• Samet Belveren,
• Sabriye Aydınoğlu,
• Mahmut Ulger,
• Abel de Cózar,
• Maria de Gracia Retamosa,
• Jose M. Sansano and
• H. Ali Döndaş

Beilstein J. Org. Chem. 2021, 17, 2812–2821, doi:10.3762/bjoc.17.192

• from LECO detection system. General procedure for ligands and complexes Synthesis of selected ligands (L1–L3): The known pyrrolidines and aroylaminocarbo-N-thioylpyrrolidine compounds (L1–L3) were synthesized according to published procedures [15]. Preparation of Ni(II) and Pd(II) complexes (L1-M, L2-M

The PIFA-initiated oxidative cyclization of 2-(3-butenyl)quinazolin-4(3H)-ones – an efficient approach to 1-(hydroxymethyl)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-ones

• Alla I. Vaskevych,
• Nataliia O. Savinchuk,
• Ruslan I. Vaskevych,
• Eduard B. Rusanov,
• Oleksandr O. Grygorenko and
• Mykhailo V. Vovk

Beilstein J. Org. Chem. 2021, 17, 2787–2794, doi:10.3762/bjoc.17.189

• (doublet), t (triplet), dd (doublet of doublet), q (quartet), m (multiplet) and br s (broad singlet). LC–MS spectra were recorded on an Agilent 1100 Series high-performance liquid chromatograph equipped with a diode matrix with an Agilent LC\MSD SL mass selective detector. Mass spectrometric detection of

GlycoBioinformatics

• Kiyoko F. Aoki-Kinoshita,
• Frédérique Lisacek,
• Niclas Karlsson,
• Daniel Kolarich and
• Nicolle H. Packer

Beilstein J. Org. Chem. 2021, 17, 2726–2728, doi:10.3762/bjoc.17.184

• tightly connected to mainstream bioinformatics. For example, databases and tools from genomics can be used for gaining information about genes encoding for glycosyltransferases, glycosidases, and glycan-binding proteins (lectins), and search engines initially designed for the detection of

Cryogels: recent applications in 3D-bioprinting, injectable cryogels, drug delivery, and wound healing

• Luke O. Jones,
• Leah Williams,
• Tasmin Boam,
• Martin Kalmet,
• Chidubem Oguike and
• Fiona L. Hatton

Beilstein J. Org. Chem. 2021, 17, 2553–2569, doi:10.3762/bjoc.17.171

• stem cells in cell-based therapies, detection of low levels of biomarkers in the blood (i.e., tumour cells, pathogenic microorganisms, etc.) for disease diagnosis, and general isolation of biological substances for clinical and environmental microbiology hold opportunities for cryogels [13][42][61

Nomimicins B–D, new tetronate-class polyketides from a marine-derived actinomycete of the genus Actinomadura

• Zhiwei Zhang,
• Tao Zhou,
• Taehui Yang,
• Keisuke Fukaya,
• Enjuro Harunari,
• Shun Saito,
• Katsuhisa Yamada,
• Chiaki Imada,
• Daisuke Urabe and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2021, 17, 2194–2202, doi:10.3762/bjoc.17.141

• give 0.23 g of brown oil that was further purified by preparative HPLC (Cosmosil 5C18-ARII, 10 × 250 mm, 4 mL/min, UV detection at 254 nm) with 73% MeCN in 0.1% HCO2H solution to yield nomimicin A (4, 33 mg, tR 21.5 min). Fractions 5 (2:1) and 6 (1:1) were combined and concentrated to provide 0.48 g of

• 5C18-ARII, 10 × 250 mm, 4 mL/min, UV detection at 254 nm) with 52% MeCN in 0.1% HCO2H solution to yield nomimicin B (1, 16.1 mg, tR 19.5 min) and nomimicin C (2, 12.2 mg, tR 21.5 min). Similarly, evaporation of the solvent gave 3.0 g of extract from 2 L of A11M culture. The extract was subjected to

• :3, and 8:2, v/v). The ODS fraction 5 (6:4) was concentrated to give 72.6 mg of semipure material. Final purification using preparative HPLC (Cosmosil XTerra Prep RP18, 10 × 250 mm, 4 mL/min, UV detection at 254 nm) with 38% MeCN in 10 mM NH4HCO3 solution yielded nomimicin D (3, 6.0 mg, tR 30.5 min

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

• ]. Following the assumption (formation of triselenide 145) made by Wilshire [94] together with the detection of the oxidized products isatins in the reaction mixture, a disproportionation mechanism of SeO2 can be drawn giving bis(indol-3-yl)triselenide 145 and SeVI (Scheme 18e). The triselenide 145 converts

Progress and challenges in the synthesis of sequence controlled polysaccharides

• Giulio Fittolani,
• Theodore Tyrikos-Ergas,
• Denisa Vargová,
• Manishkumar A. Chaube and
• Martina Delbianco

Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

• Renato L. Carvalho,
• Amanda S. de Miranda,
• Mateus P. Nunes,
• Roberto S. Gomes,
• Guilherme A. M. Jardim and
• Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

Cerium-photocatalyzed aerobic oxidation of benzylic alcohols to aldehydes and ketones

• Girish Suresh Yedase,
• Sumit Kumar,
• Jessica Stahl,
• Burkhard König and
• Veera Reddy Yatham

Beilstein J. Org. Chem. 2021, 17, 1727–1732, doi:10.3762/bjoc.17.121

• transfer (LMCT) process, which reduces the CeIV species to CeIII, similarly as reported by Zuo and co-workers [57]. We chose (n-Bu4N)2CeIVCl6 as the CeIV source to ensure a sufficient solubility in organic solvents and to facilitate the detection of the species. The CeIV(OBn)Cln complex was prepared by

A systems-based framework to computationally describe putative transcription factors and signaling pathways regulating glycan biosynthesis

• Theodore Groth,
• Rudiyanto Gunawan and
• Sriram Neelamegham

Beilstein J. Org. Chem. 2021, 17, 1712–1724, doi:10.3762/bjoc.17.119

• , glycosaminoglycans, and glycolipids. Thus, multiple glycan changes may accompany oncological transformation. TF–glycogene communities in luminal and basal breast cancer Cytoscape plots were generated for luminal breast cancer (Figure 4a). Here, using the bipartite graph community detection methods [20], we

• (TFs and glycogenes), we treated TF–glycogene networks as bipartite and applied the corresponding procedure for community detection [20]. Firstly, the bipartite TF–glycogene graphs are projected into two different unipartite graphs, where TFs and glycogenes are placed into separate graphs. The edge

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

• underexplored technology [131]. Chemically reactive crosslinking PNA nucleobases: PNA has become a highly useful probe for detection of nucleic acids. Not surprisingly, chemists have developed reactive nucleobases for covalently crosslinking PNA and nucleic acid targets. 4-Amino-6-oxo-2-vinylpyrimidine (AOVP

• in cells and animal models Delivery and uptake of oligonucleotides to target tissues and cells is one of the greatest challenges for development of nucleic acid detection probes and therapeutics [14]. This problem is especially critical for in vivo applications of PNA because unmodified PNA, despite

Recent advances in the application of isoindigo derivatives in materials chemistry

• Andrei V. Bogdanov and
• Vladimir F. Mironov

Beilstein J. Org. Chem. 2021, 17, 1533–1564, doi:10.3762/bjoc.17.111

• = 0.07 cm2⋅V−1⋅s−1. Isoindigo-based sensor devices Isoindigo derivatives have begun to find an application in the design of sensor devices for the detection of simple and complex molecules in various aggregation states. Thus, it was shown that polymer structures based on isoindigo and thiophene 59a,b and

• towards n-butanol. The lower limit of detection was 100 ppm with a response time of less than 10 s. The ability of polymeric isoindigo derivatives to strongly bind to carbon nanotubes due to π-stacking was used to create sensors for the determination of NO2 in the gaseous state (see polymer 61) and

• glucose in solution (see polymer 62) [108][109]. The limit of sensitivity of the sensor for nitrogen dioxide was 60 ppm and for glucose 0.026 mM. For the example of the fairly simple arylamine series 63, the possibility of using isoindigo polymer for the detection of explosives (trinitrophenol and