Themed collection Organic & Biomolecular Chemistry HOT article collection
Transition metal-free synthesis of alkyl pinacol boronates
This review systematically outlined the research in the area of transition metal free synthesis of alkyl pinacol boronates, which are versatile and important scaffolds to construct diverse organic compounds.
Copper-catalysed radical reactions of alkenes, alkynes and cyclopropanes with N–F reagents
The mild generation of nitrogen-centred radicals from N–F reagents using copper-based catalysts has become a convenient synthetic tool.
Cobalt-catalyzed carbonylation of the C–H bond
Direct carbonylation of the C–H bond is a great tool for installing a carbonyl group in a wide variety of substrates.
Synthesis strategies for non-symmetric, photochromic diarylethenes
This review surveys synthesis strategies for accessing non-symmetric diarylethene photochromes and highlights notable properties and applications of these compounds.
Synthetic approaches and applications of sulfonimidates
This review encompasses the developments in sulfonimidate chemistry, focusing on both syntheses and applications of these important organosulfur(VI) species.
Rational design of small molecule fluorescent probes for biological applications
Guidelines based on photophysical tuning, reactivity, isomerization, and energy transfer for rational design of synthetic fluorescent probes for biological systems.
The curious yellow colouring matter of the Iceland poppy
This account provides an chronological overview of the fascinating history of the pigment responsible for the yellow colour of the Iceland poppy (Papaver nudicaule).
TLR2 agonists and their structure–activity relationships
We review the structure–activity relationships and synthetic studies of TLR2 agonists – important chemical targets in immunotherapy.
Chemical methods for modification of proteins
The field of protein bioconjugation draws attention from stakeholders in chemistry, biology, and medicine. This review provides an overview of the present status, challenges, and opportunities for organic chemists.
Multiphosphorylated peptides: importance, synthetic strategies, and applications for studying biological mechanisms
Advances in the synthesis of multiphosphorylated peptides and peptide libraries: tools for studying the effects of phosphorylation patterns on protein function and regulation.
Insights into DNA catalysis from structural and functional studies of the 8-17 DNAzyme
The review examines functional knowledge gathered over two decades of research on the 8-17 DNAzyme, focusing on three aspects: the structural requirements for catalysis, the role of metal ions and the participation of general acid-base catalysis.
Staphylococcus aureus capsular polysaccharides: a structural and synthetic perspective
This review surveys known structures of staphylococcal polysaccharides and summarizes all synthetic efforts to obtain these sequences.
Recent trends in catalytic sp3 C–H functionalization of heterocycles
In this mini-review, we attempt to highlight gaps in existing techniques for sp3 C–H activation adjacent to heterocycles.
Construction of an IMiD-based azide library as a kit for PROTAC research
As a promising protein degradation strategy, PROTAC technology is increasingly becoming a new star in cancer treatment.
A mild and chemoselective CALB biocatalysed synthesis of sulfoxides exploiting the dual role of AcOEt as solvent and reagent
Sulfoxides have been synthesised from various sulfide substrates under mild conditions exploiting CALB biocatalyst in the presence of urea hydrogen peroxide and AcOEt which acts with the dual role of solvent and reagent.
Mannich-type allylic C–H functionalization of enol silyl ethers under photoredox–thiol hybrid catalysis
The synergy of an Ir-based photosensitizer with mild oxidizing ability and a thiol catalyst enables efficient allylic C–H functionalization of enol silyl ethers with imines under visible light irradiation.
A scalable continuous photochemical process for the generation of aminopropylsulfones
An efficient continuous photochemical process is presented that delivers a series of novel γ-aminopropylsulfones via a tetrabutylammonium decatungstate (TBADT) catalysed HAT-process.
Chemoselective activation of ethyl vs. phenyl thioglycosides: one-pot synthesis of oligosaccharides
Ethyl thioglycosides could be selectively activated in the presence of phenyl thioglycosides carrying the same or even more armed protecting group pattern.
Total synthesis of thioamycolamide A via a biomimetic route
A concise total synthesis of thioamycolamide A was accomplished as a key step of thio-Michael addition via a biomimetic route.
Chemo- and regioselective synthesis of polysubstituted 2-aminothiophenes by the cyclization of gem-dibromo or gem-dichloroalkenes with β-keto tertiary thioamides
A facile and practical method for the synthesis of 2,3,4-trisubstituted 2-aminothiophenes by the cyclization of gem-dibromoalkenes or gem-dichloroalkenes with β-keto tertiary thioamides has been developed.
Highly stereocontrolled total synthesis of secodolastane diterpenoid isolinearol
The first total synthesis of the secodolastane diterpenoid isolinearol in both racemic and enantioenriched forms has been achieved with high stereoselectively.
Selective construction of alkaloid scaffolds by alcohol-based direct and mild aerobic oxidative Pictet–Spengler reactions
Tetrahydro-β-carboline and β-carboline alkaloid scaffolds can be selectively obtained by direct aerobic oxidative Pictet–Spengler reactions of tryptamines with alcohols using TBN/TEMPO as the catalysts and oxygen as the oxidant under mild conditions.
Rapid access to 3-indolyl-1-trifluoromethyl-isobenzofurans by hybrid use of Lewis/Brønsted acid catalysts
Expeditious synthesis of 3-indolyl-1-trifluoromethyl-isobenzofurans via [1,4]-hydride shift/cyclization/intermolecular nucleophilic addition reaction sequence.
Hydroquinone and benzoquinone-catalyzed aqueous Knoevenagel condensation
Aqueous Knoevenagel condensation of various aldehydes with malononitrile could efficiently proceed using hydroquinone and benzoquinone as mixed catalysts.
Boracene-based alkylborate enabled Ni/Ir hybrid catalysis
Boracene-based alkylborate enabled visible light-mediated Ni/Ir metallaphotoredox catalysis.
Defluorination of 4-fluorothreonine by threonine deaminase
Threonine deaminase from E. coli catalyses defluorination on 4-fluorothreonine.
BINOL derivatives-catalysed enantioselective allylboration of isatins: application to the synthesis of (R)-chimonamidine
3-Allyl-3-hydroxyoxindoles are obtained with high ee in a metal-free catalytic process from isatins. This scaffold has been converted to the natural product chimonamidine.
Electrochemical synthesis of selenyl-dihydrofurans via anodic selenofunctionalization of allyl-naphthol/phenol derivatives and their anti-Alzheimer activity
Herein, we report an eco-friendly, electrosynthetic approach for the intramolecular oxyselenylation of allyl-naphthol/phenol derivatives.
Disulphide-mediated site-directed modification of proteins
Site-directed addition of a single thiols handle to proteins by means of temporary disulphide rebridging of solvent exposed disulphides is obtained with a new labelling reagent.
Sesquiterpene synthases for bungoene, pentalenene and epi-isozizaene from Streptomyces bungoensis
A sesquiterpene synthase from Streptomyces bungoensis was characterised and produces the new compound bungoene.
Site-selective modification of proteins using cucurbituril as supramolecular protection for N-terminal aromatic amino acids
Supramolecular protection of N-terminal aromatic amino acids through complexation with cucurbituril can enable site-selective protein modification of unfavored motifs.
Differential scanning fluorimetry (DSF) screen to identify inhibitors of Hsp60 protein–protein interactions
Homo-oligomers are difficult drug targets. Here, Differential Scanning Fluorimetry (DSF) is introduced as a method to identify inhibitors of these systems, by discriminating between oligomers and monomers based on their thermal stability.
Rapid sodium periodate cleavage of an unnatural amino acid enables unmasking of a highly reactive α-oxo aldehyde for protein bioconjugation
A genetically incorporated ThrK unnatural amino acid can undergo rapid periodate oxidation to reveal a reactive internal α-oxo aldehyde.
Hierarchical self-assembly of an azobenzene dyad with inverted amide connection into toroidal and tubular nanostructures
Inversion of the amide connectivity of an azobenzene dyad, which self-assembles into chiral toroids and nanotubes, improves the thermal stability of the assemblies, however it negatively affects supramolecular chirality.
Heterologous expression of the trichostatin gene cluster and functional characterization of N-methyltransferase TsnB8
N-Methyltransferase TsnB8 was demonstrated to catalyze successive methyltransfer reactions in the biosynthesis of trichostatin.
A Rh-catalyzed three-component reaction for the diastereoselective synthesis of pyrazolone derivatives with contiguous quaternary stereocenters
Efficient approach for the facile construction of polyfunctionalized pyrazolone derivatives bearing two contiguous quaternary stereocenters in good yields with high regioselectivities and excellent diastereoselectivities.
Enantioselective synthesis and determination of the absolute configuration of the male sex pheromone of the parasitoid wasp Urolepis rufipes
The parasitoid wasp Urolepis rufipes uses terminally oxidized dihydrolinalool as a sex pheromone. The absolute configuration of the active enantiomer was established as 2S,6S by synthesis and its pheromonal activity was proven in a bioassay.
Introducing sequential aza-amino acids units induces repeated β-turns and helical conformations in peptides
A major current issue in medicinal chemistry is the design of small peptide analogues resistant to proteolysis and able to adopt preferential conformations, while preserving the selectivity and efficiency of natural peptides.
Protein labeling approach to improve lysosomal targeting and efficacy of antibody–drug conjugates
An anti-EGFR nanobody was labeled at the C-terminus with a lysosome-sorting NPGY (Asn-Pro-Gly-Tyr) motif via sortase-mediated ligation to enhance the clathrin-mediated endocytosis.
Pseudo-enantiomeric carbohydrate-based N-heterocyclic carbenes as promising chiral ligands for enantiotopic discrimination
The practical synthesis of pseudo-enantiomeric carbohydrate-based NHC–Rh complexes bearing C1 or C3 sterically differentiated positions is reported. We show that steric bulk at either C1 or C3 leads to enantiotopic discrimination in the hydrosilylation of acetophenone.
Non-biaryl atropisomerism at the C–B bond in sterically hindered aminoarylboranes
Sterically hindered aminoarylboranes with atropisomerism about the C–B bond were prepared and resolved by chiral stationary phase HPLC.
Merging singlet-oxygen induced furan oxidations with organocatalysis: synthesis of enantiopure cyclopentanones and hydrindanes
A general, flexible and highly effective method for the regio-, diastereo- & enantioselective one-pot synthesis of important carbocycles, namely, enantiopure cyclopentanones and their hydrindane congeners is presented.
Synthetic-biology-based discovery of a fungal macrolide from Macrophomina phaseolina
Genome mining and heterologous biosynthesis led to the discovery of a 12 membered macrolide from Macrophomina phaseolina.
Organocatalytic carbon dioxide fixation to epoxides by perfluorinated 1,3,5-triols catalysts
A new type of perfluorinated triol catalysts of enhanced acidity was developed for the selective opening of epoxide to carbonates. This useful transformation using TBAI as co-catalyst is performed under only 1 atmosphere of CO2 at 30 to 80 °C.
Homoallylic amines as efficient chiral inducing frameworks in the conjugate addition of amides to α,β-unsaturated esters. An entry to enantio-enriched diversely substituted amines
The diastereoselective conjugate addition of chiral secondary lithium homoallylamides to α,β-unsaturated esters, providing tertiary amines bearing two chains integrating a stereogenic center adjacent to the nitrogen atom, is reported.
Regioselective catalytic asymmetric N-alkylation of isoxazol-5-ones with para-quinone methides
A highly regioselective and enantioselective N-alkylation of isoxazol-5-ones with para-quinone methides has been developed to obtain enantioenriched N-diarylmethane substituted isoxazolinones with high yields and enantioselectivities.
Metal-free synthesis of imino-disaccharides and calix-iminosugars by photoinduced radical thiol–ene coupling (TEC)
Deprotected iminosugar alkenes were subjected to thiol–ene coupling with deprotected sugar thiols to afford new imino-disaccharides. Two thiol–ene couplings converted these alkenes into iminosugar thiols and then multivalent iminosugars.
Functionalised thermally induced phase separation (TIPS) microparticles enabled for “click” chemistry
In this study we describe a novel platform for generating functionalised TIPS microparticles for “click” conjugation to various active compounds.
Reagent controlled stereoselective synthesis of teichoic acid α-(1,2)-glucans
Additive controlled glycosylation reactions are used for the construction of α-(1,2)-glucosidic linkages, such as those featuring in E. faecalis lipoteichoic acid.
Robust synthesis of NIR-emissive P-rhodamine fluorophores
A library of P-rhodamines was prepared via a new robust sequence that creates the core heterocycle by addition of diaryllithium reagents to esters. The first SAR study for P-rhodamines shows that they are NIR-emissive and highly bright fluorophores.
Cobalt-catalyzed regioselective hydrohydrazination of epoxides
A series of valuable 1,1-hydrazinoalcohols were conveniently synthesized by catalytic hydrohydrazination of epoxides with the NH group of hydrazines.
γ-C (sp3)–H bond functionalisation of α,β-unsaturated amides through an umpolung strategy
The nucleophilic γ-phenylation and γ-alkylation of α,β-unsaturated amides have been developed.
Automated access to well-defined ionic oligosaccharides
Automated Glycan Assembly grants access to ionic oligosaccharides for structural studies.
The strategic use of para-quinone methides to access synthetically challenging and chemoselective α,α′-diarylmethyl N-glycosides from unprotected carbohydrate amines
A practical route to access synthetically challenging and chemoselective α,α′-diarylmethyl N-glycosides via Sc(OTf)3-catalyzed 1,6-conjugate addition of unprotected amino sugars with p-QMs.
Enantioselective catalytic synthesis of α-aryl-α-SCF3-β2,2-amino acids
Novel α-trifluoromethylthiolated-β2,2-amino acids were obtained in high enantiopurities under chiral phase-transfer catalysis.
Ag-Catalyzed minisci C–H difluoromethylarylation of N-heteroarenes
A mild silver-catalyzed decarboxylative C–H difluoromethylarylation of electron-deficient N-heteroarenes.
Activation barriers in Class F G protein-coupled receptors revealed by umbrella sampling simulations
Molecular simulations reveal energetic barriers to Class F GPCR activation.
Kinase and GPCR polypharmacological approach for the identification of efficient anticancer medicines
Bifunctional molecules that inhibit casein kinase 1 delta and simultaneously antagonize muscarinic acetylcholine receptor M3 were identified.
Using engineered 6-O-sulfotransferase to improve the synthesis of anticoagulant heparin
Heparan sulfate (HS) and heparin are sulfated polysaccharides exhibiting diverse physiological functions.
Synthesis and antiproliferative effect of the proposed stereoisomer of the marine sponge metabolite halisphingosine A
The purported isomer of halisphingosine A was built up in 11 steps and 29% yield by catalytic Henry and hydrogenation reactions. Its 13C-NMR data differed from that of the natural isolate. It was antiproliferative in various tumour cells.
Facile synthesis of sulfotyrosine-containing α-conotoxins
A one-pot neopentyl deprotection and oxidative disulfide pairing strategy was developed for the facile synthesis of sulfotyrosine (sY)-containing α-conotoxins (Ctx).
Synthesis of 2-bromo- and 2-phenyl-neo-confused porphyrins
New examples of neo-confused porphyrins are reported. These retain global diatropic characteristics but are relatively unstable in solution.
Metabolites of the anaerobic degradation of diethyl ether by denitrifying betaproteobacterium strain HxN1
The constitutions of five metabolites formed during anaerobic degradation of diethyl ether by the denitrifying bacterium Aromatoleum sp. HxN1 were identified by comparison with synthesized standards using GC-MS.
Connecting the conformational behavior of cyclic octadepsipeptides with their ionophoric property and membrane permeability
Binding of cations leads to inversion of conformational preference of cyclic octadepsipeptides and may be connected to incorporation in membranes.
Synthesis of N-acetylglucosamine and N-acetylallosamine resorcinarene-based multivalent β-thio-glycoclusters: unexpected affinity of N-acetylallosamine ligands towards Wheat Germ Agglutinin
Resorcinarene-based glycoclusters bearing β-S-GlcNAc and β-S-AllNAc residues were synthesized and ITC and molecular docking calculations provided evidence of their strong affinity towards WGA.
Mechanistic insights into Smiles rearrangement. Focus on π–π stacking interactions along the radical cascade
The synthesis of new arene and heteroarene scaffolds of therapeutic interest has generated a renewed interest in the domino radical cyclisation–Smiles.
Revisiting the role of acids and hydrogen bond acceptors in enamine formation
A systematic investigation into the effects of acids and hydrogen bond acceptors on the reaction rates and equilibria of enamine formation is reported.
Absolute handedness control of oligoamide double helices by chiral oxazolylaniline induction
Aromatic oligoamide double helices bearing a chiral oxazolylaniline moiety were synthesized and their helix handedness was completely controlled (de > 99%).
Influence of the reducing-end anomeric configuration of the Man9 epitope on DC-SIGN recognition
The anomeric configuration of the reducing end of Man9 does not influence the binding to DC-SIGN.
Novel synthetic strategy towards subphthalocyanine-functionalized acetylenic scaffolds via various dibromo-enynes
Axial alkynylation of boron subphthalocyanine with dibromo-substituted enynes and enediynes is presented and the convenient use of these compounds for subsequent metal-catalyzed coupling reactions.
About this collection
This on-going collection features all the articles published in Organic & Biomolecular Chemistry in 2020 that were highlighted by the reviewers of these articles as being interesting or having particularly significant research.
Congratulations to all the authors whose articles are featured!