The effect of neighbouring group participation and possible long range remote group participation in O-glycosylation

• Rituparna Das and
• Balaram Mukhopadhyay

Beilstein J. Org. Chem. 2025, 21, 369–406, doi:10.3762/bjoc.21.27

• characterisation of the isolated samples significantly arduous and faulty. Therefore, the syntheses of these important carbohydrates through chemical means became inevitable to elucidate the structure unambiguously and to get hold of their biological implications with minimal doubt [17]. The oligosaccharide

Discovery of ianthelliformisamines D–G from the sponge Suberea ianthelliformis and the total synthesis of ianthelliformisamine D

• Sasha Hayes,
• Yaoying Lu,
• Bernd H. A. Rehm and
• Rohan A. Davis

Beilstein J. Org. Chem. 2024, 20, 3205–3214, doi:10.3762/bjoc.20.266

• minor and previously undescribed natural products for full characterisation studies and biological assessment. The spectroscopic and spectrometric data of all known compounds isolated during our studies matched well with the literature values [7][14]. Ianthelliformisamine D (4) was isolated as a stable

• available [16] but neither of these compounds has been fully characterised with only the total synthesis of 7 being reported in the literature [8]. Our study reports the first identification of 6 and 7 from a natural origin and the first full characterisation of these molecules using NMR, UV, and MS data

• ]. Conclusion In summary, we report here the discovery and full characterisation of four new natural products, ianthelliformisamines D–G from the marine sponge Suberea ianthelliformis. Furthermore, we describe the first total synthesis of ianthelliformisamine D which contains a rare N-(3-aminopropyl)-2

The charge transport properties of dicyanomethylene-functionalised violanthrone derivatives

• Sondos A. J. Almahmoud,
• Joseph Cameron,
• Dylan Wilkinson,
• Michele Cariello,
• Claire Wilson,
• Alan A. Wiles,
• Peter J. Skabara and
• Graeme Cooke

Beilstein J. Org. Chem. 2024, 20, 2921–2930, doi:10.3762/bjoc.20.244

• where some devices failed due to high resistance and testing was carried out using 5 μm channel length due to the low currents measured at higher channel lengths. Testing was carried out using a Keithley 4200 Semiconductor Characterisation System. Charge mobility was calculated in the saturation regime

Applications of microscopy and small angle scattering techniques for the characterisation of supramolecular gels

• Connor R. M. MacDonald and
• Emily R. Draper

Beilstein J. Org. Chem. 2024, 20, 2608–2634, doi:10.3762/bjoc.20.220

• Connor R. M. MacDonald Emily R. Draper School of Chemistry, University of Glasgow, Glasgow, Scotland, G12 8QQ, UK 10.3762/bjoc.20.220 Abstract When evaluating soft self-assembling materials for use in any application, the structural or morphological characterisation is highly important. We know

• small angle scattering (SAS) and imaging. Scattering giving us indirect information about the systems, whereas imaging is often looking at the material directly. In this review, we discuss the benefits, caveats and power of using both these techniques separately and together for the characterisation of

• supramolecular gels. Keywords: characterisation; electron microscopy; gelators; small angle scattering; supramolecular materials; Introduction Supramolecular gels are a versatile class of materials, and are of interest in many diverse applications from energy storage to cell culture [1][2]. The versatile

Computational toolbox for the analysis of protein–glycan interactions

• Ferran Nieto-Fabregat,
• Maria Pia Lenza,
• Angela Marseglia,
• Cristina Di Carluccio,
• Antonio Molinaro,
• Alba Silipo and
• Roberta Marchetti

Beilstein J. Org. Chem. 2024, 20, 2084–2107, doi:10.3762/bjoc.20.180

• physical functions [3]. Glycoscience encompasses the comprehensive study of glycans focusing on their structural, biosynthetic, biological and evolutionary aspects [4], thus playing a central role in the identification and characterisation of the glycome’ structure and function, and in unveiling its

• . Several experimental techniques, including NMR, X-ray crystallography and Cryo-EM, can provide critical information for the characterisation of protein structure and conformation. Their widespread and wisely use permitted to experimentally determine the structures of around 200,000 proteins [78], all

Oxidative fluorination with Selectfluor: A convenient procedure for preparing hypervalent iodine(V) fluorides

• Samuel M. G. Dearman,
• Xiang Li,
• Yang Li,
• Kuldip Singh and
• Alison M. Stuart

Beilstein J. Org. Chem. 2024, 20, 1785–1793, doi:10.3762/bjoc.20.157

• deposition numbers CCDC: 2351949 and 2351950. Supporting Information File 18: Experimental procedures, characterisation data, DFT calculations and 1H, 13C and 19F NMR spectra and crystallographic data. Funding SMGD and AMS thank the School of Chemistry, University of Leicester, for their generous support

Harnessing unprotected deactivated amines and arylglyoxals in the Ugi reaction for the synthesis of fused complex nitrogen heterocycles

• Javier Gómez-Ayuso,
• Pablo Pertejo,
• Tomás Hermosilla,
• Israel Carreira-Barral,
• Roberto Quesada and
• María García-Valverde

Beilstein J. Org. Chem. 2024, 20, 1758–1766, doi:10.3762/bjoc.20.154

• characterisation. Funding Funding from MCIN/AEI/10.13039/501100011033 [grant PID2020-117610RB-I00] is gratefully acknowledged. J. G.-A. and I. C.-B. thank Consejería de Educación de la Junta de Castilla y León, European Social Fund (ESF) and ERDF for their predoctoral (J. G.-A.) and post-doctoral (I. C.-B

Methyltransferases from RiPP pathways: shaping the landscape of natural product chemistry

• Maria-Paula Schröder,
• Isabel P.-M. Pfeiffer and
• Silja Mordhorst

Beilstein J. Org. Chem. 2024, 20, 1652–1670, doi:10.3762/bjoc.20.147

• byproduct. This observation suggests a novel mechanism for indole C4 methylation by NosN [131][134]. S-Methyltransferases S-MTs are rare in RiPP biosynthesis and in natural product synthesis in general. There are few examples, and in most cases, the characterisation of the MT does not go beyond deletion

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