Effects of the aldehyde-derived ring substituent on the properties of two new bioinspired trimethoxybenzoylhydrazones: methyl vs nitro groups

• Dayanne Martins,
• Roberta Lamosa,
• Talis Uelisson da Silva,
• Carolina B. P. Ligiero,
• Sérgio de Paula Machado,
• Daphne S. Cukierman and
• Nicolás A. Rey

Beilstein J. Org. Chem. 2023, 19, 1713–1727, doi:10.3762/bjoc.19.125

• ]. Absorption correction was conducted with the multi-scan method in SADABAS software (APEX3 system) [52]. The structures were solved with directed methods in ShelxS [53] and refined with full-matrix least-square in ShelxL [53], implemented in WinGX [54] and ShelxLE [55] platforms. Non-hydrogen atoms were

Radical chemistry in polymer science: an overview and recent advances

• Zixiao Wang,
• Feichen Cui,
• Yang Sui and
• Jiajun Yan

Beilstein J. Org. Chem. 2023, 19, 1580–1603, doi:10.3762/bjoc.19.116

• functionalization of optically active polymers [106]. Theato and co-workers introduced vinyl/alkyne-bearing poly(vinyl ether)s [107], poly(vinylcyclopropanes) [108], and poly(allyl 2-ylideneacetate) [109] as promising new platforms compatible to thiol–ene chemistry. Atom transfer radical addition (ATRA) is another

Photoredox catalysis harvesting multiple photon or electrochemical energies

• Mattia Lepori,
• Simon Schmid and
• Joshua P. Barham

Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81

• first efforts in this direction [32][33]. Finally, both techniques are amenable to large-scale synthesis and ideally integrated with state-of-the-art reactor technology platforms, such as continuous flow reactors and high throughput screening plates. Various examples of scalability will be highlighted

Nucleophile-induced ring contraction in pyrrolo[2,1-c][1,4]benzothiazines: access to pyrrolo[2,1-b][1,3]benzothiazoles

• Ekaterina A. Lystsova,
• Maksim V. Dmitriev,
• Andrey N. Maslivets and
• Ekaterina E. Khramtsova

Beilstein J. Org. Chem. 2023, 19, 646–657, doi:10.3762/bjoc.19.46

•  4). Results and Discussion It is known that [e]-fused 1H-pyrrole-2,3-diones (FPDs) (Figure 2) are versatile synthetic platforms enabling the synthesis of numerous heterocyclic species [33][34][35][36]. They are polyelectrophilic compounds, bearing five electrophilic centers, whose reactivity

Total synthesis of insect sex pheromones: recent improvements based on iron-mediated cross-coupling chemistry

• Eric Gayon,
• Guillaume Lefèvre,
• Olivier Guerret,
• Adrien Tintar and
• Pablo Chourreu

Beilstein J. Org. Chem. 2023, 19, 158–166, doi:10.3762/bjoc.19.15

• synthetic procedures applied to obtain a variety of insect pheromones. The present report summarizes the recent progresses made in insect sex pheromone synthetic applications in our group, with a particular focus on the quest for non-toxic and sustainable catalytic platforms developed in the iron-catalyzed

Combining the best of both worlds: radical-based divergent total synthesis

• Kyriaki Gennaiou,
• Antonios Kelesidis,
• Maria Kourgiantaki and
• Alexandros L. Zografos

Beilstein J. Org. Chem. 2023, 19, 1–26, doi:10.3762/bjoc.19.1

• platforms [66], the group considered a system in which a photoexcited catalyst oxidatively cleaves a siloxycyclopropane with endo selectivity [67], leading to aryl–nickel capture and reductive elimination. Thus, when substrates 121 and 122 were photoirradiated with blue LED light at 45 °C in the presence of

Inline purification in continuous flow synthesis – opportunities and challenges

• Jorge García-Lacuna and
• Marcus Baumann

Beilstein J. Org. Chem. 2022, 18, 1720–1740, doi:10.3762/bjoc.18.182

• presented a detailed review on continuous crystallizations of pharmaceutical compounds which discusses these approaches [108]. It is in the field of crystallization where the biggest gap between industry and academia is visible. While industry has large downstream platforms to purify APIs, academia is at a

Navigating and expanding the roadmap of natural product genome mining tools

• Friederike Biermann,
• Sebastian L. Wenski and
• Eric J. N. Helfrich

Beilstein J. Org. Chem. 2022, 18, 1656–1671, doi:10.3762/bjoc.18.178

• identify currently overlooked BGCs Genome mining was pivotal for the expansion of NP chemical space in the past two decades. Despite the development of more and more sophisticated genome mining platforms, in many cases where truly novel NP scaffolds were described, the NP was isolated first and only then

• primary or secondary metabolism (both ends of the spectrum) are identified using the strategies listed below the bar and subsequently excluded from further analysis. gcBGC aims at identifying as-of-yet overlooked BGCs that cannot be detected by state-of-the-art bioinformatic platforms, here referred to as

Microelectrode arrays, electrosynthesis, and the optimization of signaling on an inert, stable surface

• Kendra Drayton-White,
• Siyue Liu,
• Yu-Chia Chang,
• Sakashi Uppal and
• Kevin D. Moeller

Beilstein J. Org. Chem. 2022, 18, 1488–1498, doi:10.3762/bjoc.18.156

• ; microelectrode array; Introduction Microelectrode arrays composed of collections of electrodes that can each be individually addressed are powerful platforms for monitoring interactions between a protein target and small molecules [1][2][3][4][5][6][7][8]. In these efforts, molecules are either placed or

Design, synthesis, and evaluation of chiral thiophosphorus acids as organocatalysts

• Karen R. Winters and
• Jean-Luc Montchamp

Beilstein J. Org. Chem. 2022, 18, 1471–1478, doi:10.3762/bjoc.18.154

• , however, that the enantiomeric excess increases with an increase in bond length separation between the phosphorus and the R group. From the reaction evaluation we found that dual activation might be required from the catalyst in certain enantioselective reactions. Thus, CPA platforms that reintroduce a

1,4,6,10-Tetraazaadamantanes (TAADs) with N-amino groups: synthesis and formation of boron chelates and host–guest complexes

• Artem N. Semakin,
• Ivan S. Golovanov,
• Yulia V. Nelyubina and
• Alexey Yu. Sukhorukov

Beilstein J. Org. Chem. 2022, 18, 1424–1434, doi:10.3762/bjoc.18.148

• -TAADs with acylated amino groups are highly stable. In contrast, unprotected N-TAADs are prone to cage opening and hydrolysis, yet quaternization of the bridge-head nitrogen greatly stabilizes their structure. We have showcased that N-TAADs can serve as platforms for the design of chelating ligands and

Modular synthesis of 2-furyl carbinols from 3-benzyldimethylsilylfurfural platforms relying on oxygen-assisted C–Si bond functionalization

• Sebastien Curpanen,
• Per Reichert,
• Gabriele Lupidi,
• Giovanni Poli,
• Julie Oble and
• Alejandro Perez-Luna

Beilstein J. Org. Chem. 2022, 18, 1256–1263, doi:10.3762/bjoc.18.131

• -catalyzed cross-coupling reactions, such as arylation reactions catalyzed by Pd2(dba)3/CuI, as well as allylation and methylation reactions catalyzed by CuI⋅PPh3. C3-Benzyldimethylsilyl-appended furfurals are thus introduced as versatile platforms, providing a modular access to 3-substituted 2-furyl

• -based protocol for the catalytic C3–H silylation of furfurylimines [15]. This method allows to install a C–Si bond poised for further functionalization on the furfural unit, and thereby leads to synthetic platforms useful to access elaborated furans. This prospect was demonstrated with platforms relying

• activation [19]. Thereby, C3-triorganosilyl-substituted furfurals could be suitable platforms to develop a two-step modular approach to 3-substituted 2-furyl carbinols, entailing nucleophilic addition to the aldehyde function and oxygen-assisted electrophilic substitution of the C–Si bond (Scheme 1). Results

Synthesis of α-(perfluoroalkylsulfonyl)propiophenones: a new set of reagents for the light-mediated perfluoroalkylation of aromatics

• Durbis J. Castillo-Pazos,
• Juan D. Lasso and
• Chao-Jun Li

Beilstein J. Org. Chem. 2022, 18, 788–795, doi:10.3762/bjoc.18.79

• sophisticated platforms such as metal nanoparticles, all of which have been reviewed thoroughly in the literature [4][5][6][7][8]. However, the methods referenced so far display one or more of the following setbacks: involvement of harsh oxidants or reductants, use of expensive metal catalysts, need for

Flow synthesis of oxadiazoles coupled with sequential in-line extraction and chromatography

• Kian Donnelly and
• Marcus Baumann

Beilstein J. Org. Chem. 2022, 18, 232–239, doi:10.3762/bjoc.18.27

• significant development in continuous flow platforms, particularly in industry [16][17][18][19][20]. 1,3,4-Oxadiazoles are biologically relevant 5-membered heterocyclic compounds with various favourable pharmacokinetic properties and have been investigated as potential candidates for antiviral, antifungal and

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

Enhanced target cell specificity and uptake of lipid nanoparticles using RNA aptamers and peptides

• Roslyn M. Ray,
• Anders Højgaard Hansen,
• Maria Taskova,
• Bernhard Jandl,
• Jonas Hansen,
• Citra Soemardy,
• Kevin V. Morris and
• Kira Astakhova

Beilstein J. Org. Chem. 2021, 17, 891–907, doi:10.3762/bjoc.17.75

• platforms compatible with antiretroviral drugs. Specifically, a productive CNS delivery of such compounds is expected to reduce HIV-1-associated neurological disorders as well as to reduce HIV-1 replication at this sanctuary site [13][50][51]. We investigated the use of T7 and Tat peptides and evaluated the

Optical detection of di- and triphosphate anions with mixed monolayer-protected gold nanoparticles containing zinc(II)–dipicolylamine complexes

• Lena Reinke,
• Julia Bartl,
• Marcus Koch and
• Stefan Kubik

Beilstein J. Org. Chem. 2020, 16, 2687–2700, doi:10.3762/bjoc.16.219

• introducing a method to assess whether certain biologically relevant anions are present in an aqueous solution within a specific concentration range. Keywords: chemosensor; diphosphate; gold nanoparticles; optical sensing; triphosphate; Introduction Gold nanoparticles (AuNPs) are versatile platforms for the

Comparative ligand structural analytics illustrated on variably glycosylated MUC1 antigen–antibody binding

• Christopher B. Barnett,
• Tharindu Senapathi and
• Kevin J. Naidoo

Beilstein J. Org. Chem. 2020, 16, 2540–2550, doi:10.3762/bjoc.16.206

• software available to assist with the building up of glycosylated biomolecular systems. As opposed to manual preparation, there are glycan-specific tools and toolkits such as doGlycans [27], Glycosylator [28], and online platforms such as GLYCAM-WEB [29] and CHARMM-GUI [30]. In this work, the CHARMM-GUI

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

• ] and EuroCarbDB [49] and GlycomeDB [50] used GlycoCT [51] (Table 1). Thankfully, data from discontinued glycomics projects are not lost but were integrated into newer platforms, often with novel notations. One such example is GlyTouCan [53], which uses both GlycoCT [54] and WURCS [53] as notation

• languages. As a result, tools that interconvert between notations were developed to successfully integrate old data into new platforms. Additionally, the introduction of tools such as GlycanFormatConverter [55] to convert WURCS notations into more human-readable formats has eased the interpretation of

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

• information, coupled with the emergence of new platforms and technologies, has benefitted glycoscience to the point of enabling the detection and high-resolution determination and representation of complex glycans [1]. Increasing numbers of carbohydrate sequences have accumulated throughout extensive work in

• the tools available for the representation of a simple disaccharide: lactose (β-D-Galp-(1→4)-D-Glcp). Figure 2 shows how different web-available platforms rendered it. On the one hand, thanks to the unified nomenclature, there is no ambiguity regarding the nature of the carbohydrate represented. On

• monosaccharides show striking differences across platforms even though the appropriate colours to be used are strictly defined (https://www.ncbi.nlm.nih.gov/glycans/snfg.html#tab2). The colour discrepancy observed here means that some of the tools do not conform to SNFG standards. For some purposes, this

Hierarchically assembled helicates as reaction platform – from stoichiometric Diels–Alder reactions to enamine catalysis

• David Van Craen,
• Jenny Begall,
• Johannes Großkurth,
• Leonard Himmel,
• Oliver Linnenberg,
• Elisabeth Isaak and
• Markus Albrecht

Beilstein J. Org. Chem. 2020, 16, 2338–2345, doi:10.3762/bjoc.16.195

• processes based on the principle to use self-assembled coordination platforms (or as in the present case mixtures thereof) to control stereoselective C–C bond-forming reactions. Stereoinduction usually relies on spatial proximity of the prochiral carbon atoms and a chiral information of, e.g., a chiral

• formed helicates with mixtures of ligands as platforms to control the stereochemistry of C–C bond-forming reactions. However, it would be of great advantage to transfer the findings to catalytic C–C bond-forming reactions which are catalyzed by hierarchical helicates containing chiral ligands for

Tools for generating and analyzing glycan microarray data

• Akul Y. Mehta,
• Jamie Heimburg-Molinaro and
• Richard D. Cummings

Beilstein J. Org. Chem. 2020, 16, 2260–2271, doi:10.3762/bjoc.16.187

• ://glycosciences.med.ic.ac.uk/data.html. Description: Imperial College Microarray Data Online Portal of glycan microarray data (Figure 3B) consists of ≈160 experiments (from ≈36 publications) on a variety of microarray platforms composed of different glycans. The database includes data on antibodies, animal and plant lectins

Automated high-content imaging for cellular uptake, from the Schmuck cation to the latest cyclic oligochalcogenides

• Rémi Martinent,
• Javier López-Andarias,
• Dimitri Moreau,
• Yangyang Cheng,
• Naomi Sakai and
• Stefan Matile

Beilstein J. Org. Chem. 2020, 16, 2007–2016, doi:10.3762/bjoc.16.167

• for help with the high-content microscopy and analysis, J. A. Kritzer (Tufts University) and M. Hensel (Osnabrück University) for providing materials, and the Bioimaging and ACCESS platforms for services. Funding We thank the University of Geneva, the NCCR Chemical Biology, the NCCR Molecular Systems

Anthelmintic drug discovery: target identification, screening methods and the role of open science

• Frederick A. Partridge,
• Ruth Forman,
• Carole J. R. Bataille,
• Graham M. Wynne,
• Marina Nick,
• Angela J. Russell,
• Kathryn J. Else and
• David B. Sattelle

Beilstein J. Org. Chem. 2020, 16, 1203–1224, doi:10.3762/bjoc.16.105

• new anthelmintics, phenotypic screens involving assays of parasites or models in vitro remain important [83]. As a result, several methods and screening platforms have been developed to improve the screening speed and reliability. In this section we discuss recent phenotyping methods and systems, and

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

• conformational entropy penalty upon binding to a protein target, and the approach of constraining the ligand conformation with a ring is widely used in drug design [2]. Accordingly, with increasing interest for sp3-rich molecules, spirocyclic compounds are being considered valuable as molecular platforms for the

• molecular platforms for the generation of high-quality small molecule collections, taking advantage of their three-dimensional shape and structural bias to develop lead compounds. The combination of multicomponent KA2 and Pauson–Khand reactions using representative cyclic ketones, allylamine and