Direct synthesis of acyl fluorides from carboxylic acids using benzothiazolium reagents

• Lilian M. Maas,
• Alex Haswell,
• Rory Hughes and
• Matthew N. Hopkinson

Beilstein J. Org. Chem. 2024, 20, 921–930, doi:10.3762/bjoc.20.82

• the optimised one-pot conditions with benzylamine (4a) resulted in the formation of the desired amide product, however, significant by-products were also observed. Careful column chromatography of the crude reaction mixture allowed for the partial isolation and characterisation of the

• -trifluorotoluene as internal standard. Optimisation of the reaction conditions for the deoxygenative fluorination of 4-methylbenzoic acid using benzothiazolium reagents. Supporting Information Supporting Information File 36: Experimental procedures, characterisation data of all isolated products as well as copies

Skeletal rearrangement of 6,8-dioxabicyclo[3.2.1]octan-4-ols promoted by thionyl chloride or Appel conditions

• Martyn Jevric,
• Julian Klepp,
• Johannes Puschnig,
• Oscar Lamb,
• Christopher J. Sumby and
• Ben W. Greatrex

Beilstein J. Org. Chem. 2024, 20, 823–829, doi:10.3762/bjoc.20.74

• and X-ray structure for 24. Supporting Information Supporting information includes detailed experimental details and characterisation data, X-ray crystallography, and copies of 1H and 13C spectra for new compounds. Supporting Information File 11: Experimental details, X-ray crystallography and

A laterally-fused N-heterocyclic carbene framework from polysubstituted aminoimidazo[5,1-b]oxazol-6-ium salts

• Andrew D. Gillie,
• Matthew G. Wakeling,
• Bethan L. Greene,
• Louise Male and
• Paul W. Davies

Beilstein J. Org. Chem. 2024, 20, 621–627, doi:10.3762/bjoc.20.54

• . Isolated yield of 17:18 with ratios determined from the 1H NMR spectra. Supporting Information Supporting Information File 42: Experimental procedures and characterisation data, additional cyclisation studies, XRD data and NMR spectra of compounds. Acknowledgements The authors gratefully acknowledge

Photochromic derivatives of indigo: historical overview of development, challenges and applications

• Gökhan Kaplan,
• Zeynel Seferoğlu and
• Daria V. Berdnikova

Beilstein J. Org. Chem. 2024, 20, 228–242, doi:10.3762/bjoc.20.23

• 1956: first report on the photochromism of N,N'-dimethylindigo 1956–1978: extension of the range of photochromic N,N'-dialkyl and N,N'-diacetylindigos and development of experimental and theoretical approaches towards the characterisation of the photoisomerization of indigo 1979–1984: development of

Tying a knot between crown ethers and porphyrins

• Maksym Matviyishyn and
• Bartosz Szyszko

Beilstein J. Org. Chem. 2023, 19, 1630–1650, doi:10.3762/bjoc.19.120

• metals. In this perspective article, the overview of both the early designs of porphyrin-crown ether hybrids, as well as the most recent advances in the synthesis and characterisation of this remarkable group of macrocyclic systems, are addressed. The discussion covers the strategies employed in

• macrocycle. Furthermore, the formal replacement of a part of the porphyrin macrocycle with oligoethylene glycol opens further routes for constructing hybrid systems. This section will discuss syntheses, characterisation, and applications of various classes of crown ether–porphyrin architectures. Crowned

• that of the action of an accordion. The compounds possessed a large and flexible cavity that could accommodate various guest molecules and metal ions, making them intriguing hosts as well as ligands for transition metals [54]. Several studies have reported on the synthesis and characterisation of

Functional characterisation of twelve terpene synthases from actinobacteria

• Anuj K. Chhalodia,
• Houchao Xu,
• Georges B. Tabekoueng,
• Binbin Gu,
• Kizerbo A. Taizoumbe,
• Lukas Lauterbach and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2023, 19, 1386–1398, doi:10.3762/bjoc.19.100

• have been reported. Here, we report on the discovery and functional characterisation of four sesquiterpene synthases from actinomycetes with novel functions, in addition to several actinomycete terpene synthases for which functional homologs have been identified before. Results and Discussion

Germacrene B – a central intermediate in sesquiterpene biosynthesis

• Houchao Xu and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2023, 19, 186–203, doi:10.3762/bjoc.19.18

• isolated 40 (0.2 mg) were insufficient for a full spectroscopic characterisation [92]. Eudesmanes from I3 Also only a few compounds potentially arising from I3 are known (Scheme 13). Compound 18 was already discussed above and can be formed by deprotonation from I1 or I3. Cation I1 seems to be the more

• assignments and even error propagation, and shows the importance of structure elucidation by classical methods, i.e., isolation and compound characterisation by NMR spectroscopy and determination of optical rotation. Compound 51 can be generated biosynthetically from I3a through 1,2-methyl migration to I3b

Synthesis and characterisation of new antimalarial fluorinated triazolopyrazine compounds

• Kah Yean Lum,
• Jonathan M. White,
• Daniel J. G. Johnson,
• Vicky M. Avery and
• Rohan A. Davis

Beilstein J. Org. Chem. 2023, 19, 107–114, doi:10.3762/bjoc.19.11

• . Antimalarial activity was significantly reduced when C-8 of the triazolopyrazine scaffold was substituted with CF3 and CF2H moieties, whereas incorporation of a CF2Me group at the same position completely abolished antiplasmodial effects. Keywords: antimalarial; characterisation; DiversinateTM; fluorine

• triazolopyrazine compounds (10–18) via Diversinate™ chemistry. Biological data for triazolopyrazine analogues 1–18. Supporting Information Supporting Information File 134: General experimental procedures, NMR spectra and characterisation data for all new triazolopyrazine compounds and X-ray crystallography data

Using UHPLC–MS profiling for the discovery of new sponge-derived metabolites and anthelmintic screening of the NatureBank bromotyrosine library

• Sasha Hayes,
• Aya C. Taki,
• Kah Yean Lum,
• Joseph J. Byrne,
• Merrick G. Ekins,
• Robin B. Gasser and
• Rohan A. Davis

Beilstein J. Org. Chem. 2022, 18, 1544–1552, doi:10.3762/bjoc.18.164

• chromatograms, characterisation data and copies of spectra for 5-debromopurealidin H (1). Acknowledgements We gratefully acknowledge NatureBank [12] and AIMS [13] for supply of the sponge samples investigated during these studies. Funding The authors acknowledge the Australian Research Council (ARC) for

Synthesis of C6-modified mannose 1-phosphates and evaluation of derived sugar nucleotides against GDP-mannose dehydrogenase

• Sanaz Ahmadipour,
• Alice J. C. Wahart,
• Jonathan P. Dolan,
• Laura Beswick,
• Chris S. Hawes,
• Robert A. Field and
• Gavin J. Miller

Beilstein J. Org. Chem. 2022, 18, 1379–1384, doi:10.3762/bjoc.18.142

• : Detailed experimental protocols and characterisation data; spectral NMR data (1H, 13C and 31P NMR for compounds 10–17 and 19). Acknowledgements A clone encoding for GDP mannose-pyrophosphorylase from S. enterica was kindly donated by T. L. Lowary. Funding UK Research and Innovation (UKRI, Future Leaders

B–N/B–H Transborylation: borane-catalysed nitrile hydroboration

• Filip Meger,
• Alexander C. W. Kwok,
• Franziska Gilch,
• Dominic R. Willcox,
• Alex J. Hendy,
• Kieran Nicholson,
• Andrew D. Bage,
• Thomas Langer,
• Thomas A. Hunt and
• Stephen P. Thomas

Beilstein J. Org. Chem. 2022, 18, 1332–1337, doi:10.3762/bjoc.18.138

• standard); c) key steps in the DFT-computed free energies (energies calculated at M06-2X/6-311++G(d,p) on M06-2X/6-31+G(d,p)-optimised structures). Supporting Information Supporting Information File 270: Experimental details, characterisation data, and copies of NMR spectra.

Cytochrome P450 monooxygenase-mediated tailoring of triterpenoids and steroids in plants

• Karan Malhotra and
• Jakob Franke

Beilstein J. Org. Chem. 2022, 18, 1289–1310, doi:10.3762/bjoc.18.135

• limonoid biosynthesis were recently explored by functional characterisation in heterologous hosts [29][105][106][107]. There, CYP enzymes MaCYP71CD2 and MaCYP71BQ5 from Melia azedarach initiate the ring formation on the side chain of the triterpene precursor tirucalla-7,24-dien-3β-ol (19) in a sequential

Make or break: the thermodynamic equilibrium of polyphosphate kinase-catalysed reactions

• Michael Keppler,
• Sandra Moser,
• Henning J. Jessen,
• Christoph Held and
• Jennifer N. Andexer

Beilstein J. Org. Chem. 2022, 18, 1278–1288, doi:10.3762/bjoc.18.134

• for the PPK1 and PPK2-catalysed reactions with polyP as a phosphate donor since studies mainly focus on the kinetic characterisation of these enzymes. Considering the growing interest in the application of PPK enzymes, knowledge about the thermodynamic course of the reaction would be useful for the

Introducing a new 7-ring fused diindenone-dithieno[3,2-b:2',3'-d]thiophene unit as a promising component for organic semiconductor materials

• Valentin H. K. Fell,
• Joseph Cameron,
• Alexander L. Kanibolotsky,
• Eman J. Hussien and
• Peter J. Skabara

Beilstein J. Org. Chem. 2022, 18, 944–955, doi:10.3762/bjoc.18.94

• molecules as increased rigidity leads to reduced solubility [4]. This is not only a problem for both purification and characterisation, but also for device fabrication since good solubility enables facile, energy-efficient solution processing [18], e.g. spin-coating. By introducing alkyl chains, solubility

The enzyme mechanism of patchoulol synthase

• Houchao Xu,
• Bernd Goldfuss,
• Gregor Schnakenburg and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2022, 18, 13–24, doi:10.3762/bjoc.18.2

• indicate 13C-labelled carbons. Labelling experiments on the biosynthesis of patchoulol (3, part 2). Black dots indicate 13C-labelled carbons. NMR data of compound 17 (700 MHz, C6D6). Supporting Information Supporting Information File 24: Experimental details, characterisation data and copies of spectra

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

• the cryogel matrix, and shown benefits of doing this include reinforcing the matrix, increasing rigidity, and accelerating formation of pores [16][60][62]. Cryogels offer solutions to obstacles in current medicinal and therapeutic practices. In particular, specific isolation and characterisation of

Exfoliated black phosphorous-mediated CuAAC chemistry for organic and macromolecular synthesis under white LED and near-IR irradiation

• Azra Kocaarslan,
• Zafer Eroglu,
• Önder Metin and
• Yusuf Yagci

Beilstein J. Org. Chem. 2021, 17, 2477–2487, doi:10.3762/bjoc.17.164

• multifunctional monomers, Az-3 and Alk-5. Photoinduced CuAAC between benzyl azide and various alkynesa using exfoliated BPNsb in DMSO-d6 = 1 g/L. Supporting Information Supporting Information File 308: Characterisation data: 1H NMR spectra of Alk-1, Alk-2 and Alk-3, TEM, HAADF-STEM and associated EDS elemental

Allylic alcohols and amines by carbenoid eliminative cross-coupling using epoxides or aziridines

• Matthew J. Fleming and
• David M. Hodgson

Beilstein J. Org. Chem. 2021, 17, 2385–2389, doi:10.3762/bjoc.17.155

• . Supporting Information Supporting Information File 268: Experimental procedures and characterisation data for all new compounds. Acknowledgements We thank the EPSRC National Mass Spectrometry Service Centre for mass spectra. Funding The EPSRC and GlaxoSmithKline are acknowledged for a CASE studentship to M

Regioselective N-alkylation of the 1H-indazole scaffold; ring substituent and N-alkylating reagent effects on regioisomeric distribution

• Ryan M. Alam and
• John J. Keating

Beilstein J. Org. Chem. 2021, 17, 1939–1951, doi:10.3762/bjoc.17.127

• reagent effects on N-1/N-2 regioselectivity.a Supporting Information Supporting Information File 318: Compound synthesis, characterisation, and copies of spectral data pertaining to regioisomeric distribution (N-1:N-2) determination. Funding This work was supported by funding from the Eli Lilly Research

Chemical synthesis of C6-tetrazole ᴅ-mannose building blocks and access to a bioisostere of mannuronic acid 1-phosphate

• Eleni Dimitriou and
• Gavin J. Miller

Beilstein J. Org. Chem. 2021, 17, 1527–1532, doi:10.3762/bjoc.17.110

• % NaHCO3, EtOH, THF, rt, 24 h, 72%. Supporting Information Supporting Information File 218: Detailed experimental protocols and characterisation data; spectral NMR data (1H, 13C, 31P and HSQC NMR for compounds 2–5, 7–14, 16–18, 20 and 21). Acknowledgements We thank the EPSRC UK National Mass Spectrometry

Heterogeneous photocatalytic cyanomethylarylation of alkenes with acetonitrile: synthesis of diverse nitrogenous heterocyclic compounds

• Guanglong Pan,
• Qian Yang,
• Wentao Wang,
• Yurong Tang and
• Yunfei Cai

Beilstein J. Org. Chem. 2021, 17, 1171–1180, doi:10.3762/bjoc.17.89

• mechanistic study. Plausible mechanism of the CN-K-catalyzed cyanomethylarylation of alkenes. Optimization of the reaction conditions and control experimentsa. Supporting Information Supporting Information File 160: Full experimental details, compound characterisation, and copies of NMR spectra. Funding The

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

• knowledge of protein–protein interactions, common characterisation methods to characterise them, and their role in protein complex formation with some examples. A deep understanding of protein–protein interactions and their molecular interactions is important for a number of applications, including drug

• design. Protein–protein interactions and their discovery are thus an interesting avenue for understanding how protein complexes, which make up the majority of proteins, work. Keywords: characterisation methods; heterooligomeric complex; homooligomeric complex; molecular interactions; protein–protein

• ], therapeutic interventions [8], and are crucial for potential drug discoveries [9]. This minireview will give a short insight into the different characterisation methods to characterise PPIs. Moreover, it will provide an examination of the different molecular interactions of PPIs and their role in protein

Chiral anion recognition using calix[4]arene-based ureido receptors in a 1,3-alternate conformation

• Tereza Horáčková,
• Jan Budka,
• Vaclav Eigner,
• Wen-Sheng Chung,
• Petra Cuřínová and
• Pavel Lhoták

Beilstein J. Org. Chem. 2020, 16, 2999–3007, doi:10.3762/bjoc.16.249

• characterisation data (including X-ray data for 4a, 7a, and 7d, NMR, IR, and HRMS) as well as NMR titration data. Funding This research was supported by the Czech Science Foundation (Grant 20-07833S). Financial support from specific university research (Grant No. A1 FCHT 2020 010) is also acknowledged.

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

• structure as a central element in the characterisation of biological function. An adequate understanding of biomolecular mechanisms inherently requires our ability to model and visualise them. Visualisation of molecular structures is thus one of the most common tasks performed by structural biologists. As

Naphthalene diimide bis-guanidinio-carbonyl-pyrrole as a pH-switchable threading DNA intercalator

• Poulami Jana,
• Filip Šupljika,
• Carsten Schmuck and
• Ivo Piantanida

Beilstein J. Org. Chem. 2020, 16, 2201–2211, doi:10.3762/bjoc.16.185

• Information Supporting Information File 552: Spectrophotometric characterisation in solution, NMR and HRMS data, additional experimental data on interactions with DNA/RNA. Acknowledgements The authors would like to thank late Prof. Dr. Carsten Schmuck not only for his essential contribution to this work but