Leveraging glycomics data in glycoprotein 3D structure validation with Privateer

• Haroldas Bagdonas,
• Daniel Ungar and
• Jon Agirre

Beilstein J. Org. Chem. 2020, 16, 2523–2533, doi:10.3762/bjoc.16.204

• techniques produce different information – electron density (MX) or electron potential (cryo-EM) maps – but the practical considerations in terms of the atomistic interpretation hold true for both: provided that at least the secondary structural features can be resolved in a 3D map, a more or less complete

Computational tools for drawing, building and displaying carbohydrates: a visual guide

• Kanhaya Lal,
• Rafael Bermeo and
• Serge Perez

Beilstein J. Org. Chem. 2020, 16, 2448–2468, doi:10.3762/bjoc.16.199

• , 3D representation of structures is provided by tools such as Visual Molecular Dynamics (VMD) [21] , and LiteMol [22], which allow for quick analysis of structural features in 3D space. All the tools mentioned were evaluated against a set of pre-selected criteria relating to ease of use, scientific

• glycans to build up a structure quickly as compared to the normal mode, which offers options related to the structural features of complex carbohydrates (for example additional monosaccharides, isomers, ring types, etc.). The building of glycan structures uses mouse and proceeds via a selection of

Host–guest interaction of cucurbit[8]uril with oroxin A and its effect on the properties of oroxin A

• Zhishu Zeng,
• Jun Xie,
• Guangyan Luo,
• Zhu Tao and
• Qianjun Zhang

Beilstein J. Org. Chem. 2020, 16, 2332–2337, doi:10.3762/bjoc.16.194

• ][2][3]. As a consequence of the specific structural features of Q[n]s, which have two hydrophilic “portals” decorated with partially negatively charged carbonyl groups and a hydrophobic cavity [4], cucurbit[n]urils are able to form host–guest complexes with a range of drugs [5][6][7]. These complexes

Isolation and structure determination of a tetrameric sulfonyl dilithio methandiide in solution based on crystal structure analysis and ⁶Li/¹³C NMR spectroscopic data

• Jürgen Vollhardt,
• Hans Jörg Lindner and
• Hans-Joachim Gais

Beilstein J. Org. Chem. 2020, 16, 2057–2063, doi:10.3762/bjoc.16.172

• that the presence of this chain is the key to the assignment of the structure of the aggregate in solution (vide infra). The tetramer (2a)4·(THF)6 shows besides the C–Li chain a number of further interesting structural features. Lithium atom Li5 bridges an eight-membered (C–Li–O–S)2 ring at the carbon

Models of necessity

• Timothy Clark and
• Martin G. Hicks

Beilstein J. Org. Chem. 2020, 16, 1649–1661, doi:10.3762/bjoc.16.137

• for AI and ML are that it can handle all the bonding and structural features necessary to achieve the required goals (i.e., that it can describe current chemistry as completely as possible), is suitable for fast and efficient machine code based on existing or future line notations or other 2D

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis

• Stephanie G. E. Amos,
• Marion Garreau,
• Luca Buzzetti and
• Jerome Waser

Beilstein J. Org. Chem. 2020, 16, 1163–1187, doi:10.3762/bjoc.16.103

• ][20][21][22][23][24][25]. Most of these reports are organized according to the structural features of the dye and/or their applications in synthetic chemistry. In contrast, this review will focus on the different possible conceptual approaches based on organic photocatalysts for the generation of

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

• maclafungin [44], the producer of which was not identified, are metabolites of Streptomyces [33][34][35][36] or conventional rare actinomycetes [37][38]. Thus, a novel skeleton and new congeners with distinct structural features were discovered from an underexplored actinomycete of the genus Pseudosporangium

Regioselectively α- and β-alkynylated BODIPY dyes via gold(I)-catalyzed direct C–H functionalization and their photophysical properties

• Takahide Shimada,
• Shigeki Mori,
• Masatoshi Ishida and
• Hiroyuki Furuta

Beilstein J. Org. Chem. 2020, 16, 587–595, doi:10.3762/bjoc.16.53

• was also confirmed by its preliminary X-ray structure (Figure S20b, Supporting Information File 1). The 1H NMR spectra of the BODIPY derivatives in CDCl3 reflect the characteristic structural features. The proton signals assignable to the α-pyrrolic CHs appeared in the lowest field region (δ ca. 8.00

Exploring the scope of DBU-promoted amidations of 7-methoxycarbonylpterin

• Anna R. Bockman and
• Jeffrey M. Pruet

Beilstein J. Org. Chem. 2020, 16, 509–514, doi:10.3762/bjoc.16.46

• explored this reaction to assess its scope and identify structural features in the amines which significantly affect success, monitored the reaction kinetics using a pseudo-first order kinetics model, and further adapted the reaction conditions to allow for product formation in as little as 5 min, with

Ultrasonic-assisted unusual four-component synthesis of 7-azolylamino-4,5,6,7-tetrahydroazolo[1,5-a]pyrimidines

• Yana I. Sakhno,
• Maryna V. Murlykina,
• Oleksandr I. Zbruyev,
• Anton V. Kozyryev,
• Svetlana V. Shishkina,
• Dmytro Sysoiev,
• Vladimir I. Musatov,
• Sergey M. Desenko and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2020, 16, 281–289, doi:10.3762/bjoc.16.27

• "Investigation of structural features of nitrogen containing heterocycles with potential biological activity" (0119U100716). M. Murlykina was supported by the Grant of National Academy of Sciences of Ukraine for young scientists’ research laboratories and groups (0118U100275).

Combination of multicomponent KA² and Pauson–Khand reactions: short synthesis of spirocyclic pyrrolocyclopentenones

• Riccardo Innocenti,
• Elena Lenci,
• Gloria Menchi and
• Andrea Trabocchi

Beilstein J. Org. Chem. 2020, 16, 200–211, doi:10.3762/bjoc.16.23

• between Hc and Ha protons, as also shown in NOESY 2D spectrum (see Figure 2 and Supporting Information File 1). A similar analysis allowed the structural assignment for 38. Chemoinformatic analysis The structural features of the compounds so obtained and representative functionalized molecular scaffolds

Emission solvatochromic, solid-state and aggregation-induced emissive α-pyrones and emission-tuneable 1H-pyridines by Michael addition–cyclocondensation sequences

• Natascha Breuer,
• Irina Gruber,
• Christoph Janiak and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2019, 15, 2684–2703, doi:10.3762/bjoc.15.262

• achieved [4]. Small molecule organic fluorophores are particularly advantageous due to the potential of a tailored fine-tuning of their photophysical properties through synthetic modifications [5]. Based on their structural features, functionalized organic chromophores, containing N-, O- or S-atoms, are

Plasma membrane imaging with a fluorescent benzothiadiazole derivative

• Pedro H. P. R. Carvalho,
• Jose R. Correa,
• Karen L. R. Paiva,
• Daniel F. S. Machado,
• Jackson D. Scholten and
• Brenno A. D. Neto

Beilstein J. Org. Chem. 2019, 15, 2644–2654, doi:10.3762/bjoc.15.257

• microscopy. Arrows indicate the peripherical accumulation of the dyes in the plasma membranes. The letter N indicates the nuclei of the cells (scale bar of 10 μm). Synthesis of the plasma membrane BTD probe (BTD-4APTEG) and its structural features. UV–vis and fluorescence emission data (in different solvents

Anion-driven encapsulation of cationic guests inside pyridine[4]arene dimers

• Anniina Kiesilä,
• Jani O. Moilanen,
• Anneli Kruve,
• Christoph A. Schalley,
• Perdita Barran and
• Elina Kalenius

Beilstein J. Org. Chem. 2019, 15, 2486–2492, doi:10.3762/bjoc.15.241

• an endo location of the cation. Ion mobility mass spectrometry (IM-MS) is a powerful tool to study structural features such as the endo/exo complexation of supramolecular complexes [11][15][16][17][18]. Drift tube ion mobility mass spectrometry (DT-IMMS) enables the determination of structure-related

Reversible switching of arylazopyrazole within a metal–organic cage

• Anton I. Hanopolskyi,
• Soumen De,
• Michał J. Białek,
• Yael Diskin-Posner,
• Liat Avram,
• Moran Feller and
• Rafal Klajn

Beilstein J. Org. Chem. 2019, 15, 2398–2407, doi:10.3762/bjoc.15.232

• host is small and is mostly related to the positions of the Pd centers (Figure S16, Supporting Information File 1). We were pleased to find that the structural features of (E-1)22 resolved by X-ray crystallography were in full agreement with a detailed analysis of the complex’s NOE spectra (see Figure

In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines

• Irina G. Tkachenko,
• Sergey A. Komykhov,
• Vladimir I. Musatov,
• Svitlana V. Shishkina,
• Viktoriya V. Dyakonenko,
• Vladimir N. Shvets,
• Mikhail V. Diachkov,
• Valentyn A. Chebanov and
• Sergey M. Desenko

Beilstein J. Org. Chem. 2019, 15, 2390–2397, doi:10.3762/bjoc.15.231

• . Acknowledgements The authors thank the National Academy of Sciences of Ukraine for financial support in the frame of the projects "Creation of modern bases for obtaining and analyzing substances and components of materials for pharmaceutical purposes" (0119U100727) and "Investigation of structural features of

Synthesis of a dihalogenated pyridinyl silicon rhodamine for mitochondrial imaging by a halogen dance rearrangement

• Jessica Matthias,
• Thines Kanagasundaram,
• Klaus Kopka and
• Carsten S. Kramer

Beilstein J. Org. Chem. 2019, 15, 2333–2343, doi:10.3762/bjoc.15.226

• microscopy [2][3][4][5][6][7][8][9], as direct probes for various biomolecules [10][11][12][13] or as sensors for metal ions [14][15][16][17][18], pH [16], voltage [19] or metabolites [20][21][22][23]. Several attempts were made, partially supported by DFT calculations, to correlate the dyes’ structural

• features with their optical properties and control the latter by rational dye design [15][24][25][26]. These investigations led to new silicon rhodamine dyes with enhanced and fine-tuned properties (quantum yield, lifetime, brightness, absorption and emission maxima). A recent review compared the

Thermal stability of N-heterocycle-stabilized iodanes – a systematic investigation

• Andreas Boelke,
• Yulia A. Vlasenko,
• Mekhman S. Yusubov,
• Boris J. Nachtsheim and
• Pavel S. Postnikov

Beilstein J. Org. Chem. 2019, 15, 2311–2318, doi:10.3762/bjoc.15.223

• bearing N- and O-centered ligands according to our reported procedures [29][30]. The synthesized compounds then have been divided in the following discussion by their principle structural features into pseudocyclic and cyclic hydroxy(phenyl)-λ3-iodanes (Figure 2) and pseudocyclic and cyclic mesityl(phenyl

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

• the central benzene rings in 1b+ decreased by 1.31°, accompanied with a slight shortening of the N···N distances (Supporting Information File 1, Figure S5). These structural features contribute to an increase in the electronic coupling between the NAr3 units, thereby increasing the potential splitting

A review of the total syntheses of triptolide

• Xiang Zhang,
• Zaozao Xiao and
• Hongtao Xu

Beilstein J. Org. Chem. 2019, 15, 1984–1995, doi:10.3762/bjoc.15.194

• Immunochemical Studies (SIAIS), ShanghaiTech University, Shanghai, 201210, China 10.3762/bjoc.15.194 Abstract Triptolide is a complex triepoxide diterpene natural product that has attracted considerable interest in the organic chemistry and medicinal chemistry societies due to its intriguing structural features

• wilfordii Hook F; triptolide; Introduction Triptolide (1, Figure 1) is the first diterpenoid triepoxide isolated from Tripterygium wilfordii Hook F. (TWHF) in 1972 [1]. It has attracted an ever-increasing attention due to its intriguing structural features and various promising pharmacological activities

• ) syntheses using polyene cyclization to construct the core structure (route H, I, J, K, and L); iv) syntheses highlight the utilization of metal-catalyzed reactions (M and N). Review The intriguing structural features of triptolide and its relatives have provided a rich playing field for the design and

Design, synthesis and biological evaluation of immunostimulating mannosylated desmuramyl peptides

• Rosana Ribić,
• Ranko Stojković,
• Lidija Milković,
• Mariastefania Antica,
• Marko Cigler and
• Srđanka Tomić

Beilstein J. Org. Chem. 2019, 15, 1805–1814, doi:10.3762/bjoc.15.174

• affect the Th1/Th2 switch of the immune response [52]. The presented results demonstrate the great immunostimulating potential of glycolyl-modified desmuramyl peptides. Peptidoglycan fragments with mycobacterial structural features, such as synthesized compounds 20–22, could efficiently link innate and

Synthesis and biological evaluation of truncated derivatives of abyssomicin C as antibacterial agents

• Leticia Monjas,
• Peter Fodran,
• Johanna Kollback,
• Carlo Cassani,
• Thomas Olsson,
• Maja Genheden,
• D. G. Joakim Larsson and
• Carl-Johan Wallentin

Beilstein J. Org. Chem. 2019, 15, 1468–1474, doi:10.3762/bjoc.15.147

• simplified structure that still includes all structural features that have been previously found to be essential for activity. This truncated derivative still has the tetronate functionality and the enone-equipped 11-membered ring system but lacks the oxabicyclo[2.2.2]octane unit. In addition to a simplified

Doebner-type pyrazolopyridine carboxylic acids in an Ugi four-component reaction

• Maryna V. Murlykina,
• Oleksandr V. Kolomiets,
• Maryna M. Kornet,
• Yana I. Sakhno,
• Sergey M. Desenko,
• Victoriya V. Dyakonenko,
• Svetlana V. Shishkina,
• Oleksandr A. Brazhko,
• Vladimir I. Musatov,
• Alexander V. Tsygankov,
• Erik V. Van der Eycken and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2019, 15, 1281–1288, doi:10.3762/bjoc.15.126

• National Academy of Sciences of Ukraine for financial support in the frame of the projects "Creation of modern bases for obtaining and analyzing substances and components of materials for pharmaceutical purposes" (0119U100727) and "Investigation of structural features of nitrogen containing heterocycles

Novel (2-amino-4-arylimidazolyl)propanoic acids and pyrrolo[1,2-c]imidazoles via the domino reactions of 2-amino-4-arylimidazoles with carbonyl and methylene active compounds

• Victoria V. Lipson,
• Tetiana L. Pavlovska,
• Nataliya V. Svetlichnaya,
• Anna A. Poryvai,
• Nikolay Yu. Gorobets,
• Erik V. Van der Eycken,
• Irina S. Konovalova,
• Svetlana V. Shiskina,
• Alexander V. Borisov,
• Vladimir I. Musatov and
• Alexander V. Mazepa

Beilstein J. Org. Chem. 2019, 15, 1032–1045, doi:10.3762/bjoc.15.101

• of the projects "Creation of modern bases for obtaining and analyzing substances and components of materials for pharmaceutical purposes" (0119U100727) and "Investigation of structural features of nitrogen containing heterocycles with potential biological activity" (0119U100716).

Selectivity in multiple multicomponent reactions: types and synthetic applications

• Ouldouz Ghashghaei,
• Francesca Seghetti and
• Rodolfo Lavilla

Beilstein J. Org. Chem. 2019, 15, 521–534, doi:10.3762/bjoc.15.46

• the structural features of a given substrate. For instance, all known examples deal with ditopic compounds, where the two reactive FGs are conjugated. In this way, after the initial MCR, the intermediate adduct is somewhat deactivated with respect to the initial substrate, and the remaining FG is less