Facile and diastereoselective arylation of the privileged 1,4-dihydroisoquinolin-3(2H)-one scaffold

• Dmitry Dar’in,
• Grigory Kantin,
• Alexander Bunev and
• Mikhail Krasavin

Beilstein J. Org. Chem. 2022, 18, 1070–1078, doi:10.3762/bjoc.18.109

• arylation product 9. The trans-diastereoselectivity in the latter process is reasonably justified by the approach of the arene molecule to carbocation 17 from the sterically less hindered side (Scheme 5). Compounds 9 have a pronounced three-dimensional character which makes this novel chemotype a promising

• -isoquinolone byproducts (formed exclusively in the absence of the arene). The extent of this side reaction was found to be dependent on the electronic character of the 1,4-DHIQs and the carbocation-intercepting arene molecule. Considering the pronounced three-dimensional character of 1,2,4-trisubstituted 1,4

Unusual highly diastereoselective Rh(II)-catalyzed dimerization of 3-diazo-2-arylidenesuccinimides provides access to a new dibenzazulene scaffold

• Anastasia Vepreva,
• Alexander S. Bunev,
• Andrey Yu. Kudinov,
• Grigory Kantin,
• Mikhail Krasavin and
• Dmitry Dar’in

Beilstein J. Org. Chem. 2022, 18, 533–538, doi:10.3762/bjoc.18.55

• diastereomer 2a is indicative of a sequence of concerted processes with an unambiguous stereochemistry control at each step where stereogenic centers are formed. Dibenzoazulenodipyrroles 2 have a pronounced three-dimensional character which make this chemotype promising as probe for protein–protein

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

• ligand achieved the high activities of the Co-MS@MNPs/CS. Taking aryl halides and terminal alkynes as the reactants, Vajargahy and Dabiri discussed a facile method for a Sonogashira coupling reaction catalyzed by Pd/Co bimetallic nanoparticles supported on three-dimensional graphene (PdCoNPs-3DG) in

• aqueous medium under aerobic conditions (Scheme 26) [39]. The graphene support was prepared by oxidation of graphite, treatment of the resulting graphene oxide with ethylene diamine in an autoclave followed by freeze-drying to obtain three dimensional graphene with a high nitrogen content. Heating of the

Green synthesis of C5–C6-unsubstituted 1,4-DHP scaffolds using an efficient Ni–chitosan nanocatalyst under ultrasonic conditions

• Soumyadip Basu,
• Sauvik Chatterjee,
• Suman Ray,
• Suvendu Maity,
• Prasanta Ghosh,
• Asim Bhaumik and
• Chhanda Mukhopadhyay

Beilstein J. Org. Chem. 2022, 18, 133–142, doi:10.3762/bjoc.18.14

• transition metal ions due to the presence of abundant amino and alcohol groups in the structure [18]. Because of this chelating character, as well as due to the hydrophilicity, unique three-dimensional structure, and mechanical properties, chitosan has several catalytic applications [19][20]. In this work

Peptide stapling by late-stage Suzuki–Miyaura cross-coupling

• Hendrik Gruß,
• Rebecca C. Feiner,
• Ridhiwan Mseya,
• David C. Schröder,
• Michał Jewgiński,
• Kristian M. Müller,
• Rafał Latajka,
• Antoine Marion and
• Norbert Sewald

Beilstein J. Org. Chem. 2022, 18, 1–12, doi:10.3762/bjoc.18.1

• -dimensional space of PC1-3 led to 32 and 38 structural clusters for the cis and trans isomers, respectively. The first three representative structures are depicted in Figure 4, the first six clusters are projected in the three-dimensional space of PC1-3, and the corresponding representative structures are

• higher probability of occurrence (17.8%). The non-helical conformation c3 of P5 trans (7.5%) is slightly less populated than the corresponding c2 of P5 cis. The macrocycle of both isomers is found to be rather flexible, forming well-separated conformational clusters in the three-dimensional space of PC1

• simulations. The middle panel shows the three-dimensional projection of the six main PCA-based conformational clusters in the space of the first three principal components (PC). The lower panel presents a two-dimensional projection in the plane of the first two PCs. Each point corresponds to a trajectory

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

• alter cryogel pore size and mechanical properties. In addition, Tam et al. demonstrated the optical transparency with three-dimensional spatial control of immobilised bioactive growth factors using multiphoton patterning and cellular response to immobilised ligands as shown in Figure 6 [94]. Researchers

An initiator- and catalyst-free hydrogel coating process for 3D printed medical-grade poly(ε-caprolactone)

• Jochen Löblein,
• Thomas Lorson,
• Miriam Komma,
• Tobias Kielholz,
• Maike Windbergs,
• Paul D. Dalton and
• Robert Luxenhofer

Beilstein J. Org. Chem. 2021, 17, 2095–2101, doi:10.3762/bjoc.17.136

• ; surface modification; Introduction Additive manufacturing, commonly referred to as three-dimensional (3D) printing, is an approach to create physical objects using layer-by-layer [1] or voxel-by-voxel fabrication [2]. 3D printed materials can be used for a broad spectrum of applications, including

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

Breaking paracyclophane: the unexpected formation of non-symmetric disubstituted nitro[2.2]metaparacyclophanes

• Suraj Patel,
• Tyson N. Dais,
• Paul G. Plieger and
• Gareth J. Rowlands

Beilstein J. Org. Chem. 2021, 17, 1518–1526, doi:10.3762/bjoc.17.109

• chains at non-adjacent carbon positions. Their constrained three-dimensional shapes enforce unusual conformations and interactions between the aromatic decks, all of which results in their unique properties [2][3][4][5]. The most studied cyclophane is [2.2]paracyclophane (1, Figure 1). Not only is it the

Photoinduced post-modification of graphitic carbon nitride-embedded hydrogels: synthesis of 'hydrophobic hydrogels' and pore substructuring

• Cansu Esen and
• Baris Kumru

Beilstein J. Org. Chem. 2021, 17, 1323–1334, doi:10.3762/bjoc.17.92

• results confirm the photoinduced polymerization within the hydrogel network. Visible light irradiation leads to a polymerization of monomers within the three‐dimensional hydrogel network, thus one can expect altered pore morphologies. In that regard, SEM images are useful to explore the pore

Structural effects of meso-halogenation on porphyrins

• Keith J. Flanagan,
• Maximilian Paradiz Dominguez,
• Zoi Melissari,
• Hans-Georg Eckhardt,
• René M. Williams,
• Dáire Gibbons,
• Caroline Prior,
• Gemma M. Locke,
• Alina Meindl,
• Aoife A. Ryan and
• Mathias O. Senge

Beilstein J. Org. Chem. 2021, 17, 1149–1170, doi:10.3762/bjoc.17.88

• ][12][13]. Such complexes have been reported for potential application in materials sciences (e.g., molecular sieves) as they form a three-dimensional lattice where more than 50% of the crystal capacity consists of open straight channels [5][6]. Noteworthy, Titi et al. reported that a chiral

Biochemistry of fluoroprolines: the prospect of making fluorine a bioelement

• Vladimir Kubyshkin,
• Rebecca Davis and
• Nediljko Budisa

Beilstein J. Org. Chem. 2021, 17, 439–460, doi:10.3762/bjoc.17.40

• elucidate three-dimensional structures of proteins. However, the substitution of proline by one of the remaining 19 coded amino acids can be harmful to protein folding and the functional properties. This is usually explained by the absence of the amide hydrogen atom and the cyclic nature of the proline ring

¹⁹F NMR as a tool in chemical biology

• Diana Gimenez,
• Aoife Phelan,
• Cormac D. Murphy and
• Steven L. Cobb

Beilstein J. Org. Chem. 2021, 17, 293–318, doi:10.3762/bjoc.17.28

• of which were consistent with those obtained in previous work but measured in cell membrane extracts [46]. Structural analysis of macromolecules using 19F NMR The three-dimensional (3D) structure of biomacromolecules and their conformational dynamics are often the starting point for the development

The preparation and properties of 1,1-difluorocyclopropane derivatives

• Kymbat S. Adekenova,
• Peter B. Wyatt and
• Sergazy M. Adekenov

Beilstein J. Org. Chem. 2021, 17, 245–272, doi:10.3762/bjoc.17.25

Multiswitchable photoacid–hydroxyflavylium–polyelectrolyte nano-assemblies

• Alexander Zika and
• Franziska Gröhn

Beilstein J. Org. Chem. 2021, 17, 166–185, doi:10.3762/bjoc.17.17

• strength may be understood based on the molecular parameters of the building blocks and in particular the polar surface area (PSA), which relates to the three-dimensional charge distribution of the molecule. The PSA results from the area of the polar groups in the molecule taking into account the

Insight into functionalized-macrocycles-guided supramolecular photocatalysis

• Minzan Zuo,
• Krishnasamy Velmurugan,
• Kaiya Wang,
• Xueqi Tian and
• Xiao-Yu Hu

Beilstein J. Org. Chem. 2021, 17, 139–155, doi:10.3762/bjoc.17.15

• structural rigidity caused by supramolecular host–guest complexation, ii) that a restricted space, size, and volume could lead to three-dimensional translation (rotation, vibration, and translation) of the guests within the host cavities, and iii) the dynamic properties of the guest within the supramolecular

Molecular basis for protein–protein interactions

• Brandon Charles Seychell and
• Tobias Beck

Beilstein J. Org. Chem. 2021, 17, 1–10, doi:10.3762/bjoc.17.1

• containers in vitro. These highly charged variants were then used to form a binary three-dimensional assembly analogous to inorganic salts. The structure of this assembly was determined to have a 1:1 stoichiometry, with a coordination number of 12. The advantage of such systems was discussed to be that each

• protein containers to form a highly ordered three-dimensional superlattice. Figure reprinted with permission from J. Am. Chem. Soc. 2016, 138, 12731–12734 [103]. Copyright 2016 American Chemical Society. Funding This work was supported by the Exploration Grant from the Boehringer Ingelheim Foundation and

Incorporation of a metal-mediated base pair into an ATP aptamer – using silver(I) ions to modulate aptamer function

• Marius H. Heddinga and
• Jens Müller

Beilstein J. Org. Chem. 2020, 16, 2870–2879, doi:10.3762/bjoc.16.236

• mostly unstructured in solution, aptamers typically fold into their three-dimensional structure upon binding the respective target molecule [2]. Aptamers are normally identified by the in vitro selection from combinatorial libraries of nucleic acids [3]. In the past decades, interest in aptamers has

• triphosphate) [25]. The choice of this aptamer was expected to have various advantages. 1) Its three-dimensional structure has been reported [26], so the position for the incorporation of the metal-mediated base pair can be chosen in a meaningful way. 2) Its structure is based on a duplex rather than a

Dirhamnolipid ester – formation of reverse wormlike micelles in a binary (primerless) system

• David Liese,
• Hans Henning Wenk,
• Xin Lu,
• Jochen Kleinen and
• Gebhard Haberhauer

Beilstein J. Org. Chem. 2020, 16, 2820–2830, doi:10.3762/bjoc.16.232

• can be explained with an inhomogeneous breakup of the three-dimensional structure. In the beginning, the network collapses into big chunks, while the surrounding material is still rigid. A further increase in the temperature leads to a dominating viscous behavior until the whole sample becomes fluid

• caused by a slow formation of the three-dimensional network. The hysteresis gets smaller at low concentrations, indicating the approach of the critical gel-formation concentration. Deformation sweep To gather some more information about the viscoelastic material, a deformation sweep was performed. On the

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

• monosaccharide minimal-energy conformation. While these features were recognised to address some long-standing needs in carbohydrate structure determination [39][40], significant challenges remain, particularly in the scenario where the glycan composition cannot be ascertained solely from the three-dimensional

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

• aspects of glycan identification, quantification and visualisation, some of which will be further developed throughout this article. Biological molecules express their function throughout their three-dimensional structures. For this reason, structural biology places great emphasis on the three-dimensional

• glycoscience. The joint need to better perceive and manipulate the three-dimensional objects that make up molecular structures is leading to a rapid appropriation of techniques of Virtual Reality (VR) by the molecular biology community. Generic definitions describe VR as being immersion in an interactive

• constructing 3D models of glycans from a sequence using standard nomenclature accessible at http://www.glycosciences.de/modeling/sweet2/doc/index.php (Figure 9, top). This tool is available as a part of the glycosciences.de website, which also provides other options for analysing glycans in three-dimensional

One-pot synthesis of oxazolidinones and five-membered cyclic carbonates from epoxides and chlorosulfonyl isocyanate: theoretical evidence for an asynchronous concerted pathway

• Esra Demir,
• Ozlem Sari,
• Yasin Çetinkaya,
• Ufuk Atmaca,
• Safiye Sağ Erdem and
• Murat Çelik

Beilstein J. Org. Chem. 2020, 16, 1805–1819, doi:10.3762/bjoc.16.148

• energy of 16.2 kcal/mol with respect to the initial reactant complex RC1 (7f+CSI) (Figure 5). The overall process is exothermic by 56.2 kcal/mol. Three-dimensional (3D) views of all the optimized structures of path 2 are illustrated in Supporting Information File 1, Figure S2. As can be seen from the

Models of necessity

• Timothy Clark and
• Martin G. Hicks

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

• chemists represent chemical structures as two-dimensional sketches made up of atoms and bonds, simplifying the complex three-dimensional molecules comprising nuclei and electrons of the quantum mechanical description, is the everyday language of chemistry. This language uses models, particularly of bonding

Mechanochemical green synthesis of hyper-crosslinked cyclodextrin polymers

• Alberto Rubin Pedrazzo,
• Fabrizio Caldera,
• Marco Zanetti,
• Silvia Lucia Appleton,
• Nilesh Kumar Dhakar and
• Francesco Trotta

Beilstein J. Org. Chem. 2020, 16, 1554–1563, doi:10.3762/bjoc.16.127

• . Polysaccharides and, among them, starch derivatives such as cyclodextrins (CD), have recently emerged as they are safe, of low cost and biodegradable. Cyclodextrin nanosponges (CD-NS) are crosslinked cyclodextrin polymers characterized by a nanosized three-dimensional network. The reactive hydroxy groups of CDs

Heterogeneous photocatalysis in flow chemical reactors

• Christopher G. Thomson,
• Ai-Lan Lee and
• Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125