Hetero-bimetallic cooperative catalysis for the synthesis of heteroarenes
Review covering the synthesis of 5- and 6-membered as well as condensed heteroarenes, focussing on the combinations in cooperative catalytic systems in strategies used to achieve selectivity and also highlights the mode of action for the cooperative catalysis leading to the synthesis of commercially and biologically relevant heteroarenes.
Use of ArSO2SRf reagents: an efficient tool for the introduction of SRf moieties
This review discusses the use of several ArSO2SRf reagents as SRf sources, an emerging trend to access SRf-containing molecules.
Emerging applications of peptide–oligonucleotide conjugates: bioactive scaffolds, self-assembling systems, and hybrid nanomaterials
Peptide–oligonucleotide conjugates (POCs) are covalent constructs that link a molecule like DNA to a synthetic peptide sequences.
Beyond the traditional roles of Ag in catalysis: the transmetalating ability of organosilver(I) species in Pd-catalysed reactions
The role of silver salts in Pd-catalysed C–C bond forming transformations.
Intermolecular alkene difunctionalizations for the synthesis of saturated heterocycles
Intermolecular alkene difunctionalizations for the direct synthesis of saturated heterocycles.
The challenge of using isopropylamine as an amine donor in transaminase catalysed reactions
Factors that affect the efficiency of amine transaminase catalyzed reactions using isopropylamine as an amine donor.
Rearranged ergostane-type natural products: chemistry, biology, and medicinal aspects
Rearranged ergostane-type natural products are structurally intriguing and exhibit biologically relevant properties.
Next generation diversity-oriented synthesis: a paradigm shift from chemical diversity to biological diversity
Diversity-oriented synthesis adds biological performance as a new diversity element.
Recent advances in homogeneous borrowing hydrogen catalysis using earth-abundant first row transition metals
The review highlights the recent advances (2013-present) in the use of earth-abundant first row transition metals in homogeneous borrowing hydrogen catalysis.
Photoinduced decarboxylative azidation of cyclic amino acids
The direct decarboxylative azidation of cyclic α-amino acids has been achieved via visible light-mediated organo-photoredox catalysis.
ortho-Fluoroazobenzene derivatives as DNA intercalators for photocontrol of DNA and nucleosome binding by visible light
We report a high-affinity photoswitchable DNA binder, which displays different nucleosome-binding capacities upon visible-light irradiation.
Iron catalysed selective reduction of esters to alcohols
Exposure of BIANFeCl2 to nBuLi generates an anionic complex which is a competent catalyst for the selective reduction of esters to alcohols.
A fluorogenic C4N4 probe for azide-based labelling
A new fluorogenic probe based on the recently identified 2,5-diaminopyrimidine (C4N4) fluorophore is introduced for azide-specific labelling.
Using automated glycan assembly (AGA) for the practical synthesis of heparan sulfate oligosaccharide precursors
Herein we report synthesis of complex heparan sulfate oligosaccharide precursors by automated glycan assembly using disaccharide donor building blocks.
Formal [4 + 2] benzannulation of 2-alkenyl indoles with aldehydes: a route to structurally diverse carbazoles and bis-carbazoles
Construction of structurally diverse carbazoles and bis-carbazoles by protecting-group-free formal [4 + 2]-benzannulation of 2-alkenyl indoles and aldehydes is demonstrated.
Radical SAM-dependent adenosylation catalyzed by L-tyrosine lyases
Tyrosine analogues containing an olefin moiety can be adenosylated by L-tyrosine lyases.
Vinylogous acyl triflates as an entry point to α,β-disubstituted cyclic enones via Suzuki–Miyaura cross-coupling
An alternative protocol for the B-alkyl Suzuki–Miyaura reaction to produce cyclic α,β-disubstituted enones is reported.
An enantioselective synthesis of α-alkylated pyrroles via cooperative isothiourea/palladium catalysis
Herein we describe the direct enantioselective Lewis base/Pd catalysed α-allylation of pyrrole acetic acid esters.
Posttranscriptional spin labeling of RNA by tetrazine-based cycloaddition
Spin labeling of in vitro transcribed RNA by iEDDA click chemistry is demonstrated. This allows the determination of distance distributions between two nitroxide spin labels by PELDOR in a self-complementary RNA duplex.
Direct (het)arylation of tetrahydroisoquinolines via a metal and oxidant free C(sp3)–H functionalization enabled three component reaction
Direct arylation and heteroarylation of unprotected tetrahydroisoquinolines were achieved under conditions free of metals, oxidants and solvents.
Fluorescent peptide displacement as a general assay for screening small molecule libraries against RNA
A fluorescent peptide displacement assay combined with statistical analysis is used for screening small molecules against different RNA targets and profiling their affinity/selectivity patterns.
Copper-catalyzed arene amination in pure aqueous ammonia
A simple protocol for copper-catalyzed arene amination using aqueous ammonia without any additional ligands and organic coordinating solvents has been developed.
Mechanism of nitrones and allenoates cascade reactions for the synthesis of dihydro[1,2-a]indoles
Quantum mechanical calculations (DLPNO-CCSD(T) and M06-2X) are employed to gain insights into the mechanism and selectivity in the catalytic synthesis of dihydropyrido[1,2-a]indoles from the cascade reaction between nitrones and allenes.
Multicomponent dipolar cycloadditions: efficient synthesis of polycyclic fused pyrrolizidines via azomethine ylides
An efficient multicomponent dipolar cycloaddition for the synthesis of polycyclic fused pyrrolizidines was developed using N-aromatic zwitterions, aldehydes, and amino acids.
Synthesis of fluoroalkylated alkynes via visible-light photocatalysis
Fluoroalkylated alkynes, which are versatile building blocks for the synthesis of various biologically active organofluorine compounds, were synthesized from easily available alkynyl halides and fluoroalkyl halides by visible-light photocatalysis.
Total synthesis of (±)-antroquinonol
We report the total synthesis of (±)-antroquinonol based on a concise and efficient route.
Chiral selenide-catalyzed enantioselective synthesis of trifluoromethylthiolated 2,5-disubstituted oxazolines
Chiral selenide-catalyzed enantioselective trifluoromethylthiolation of 1,1-disubstituted alkenes is disclosed. Various chiral trifluoromethylthiolated 2,5-disubstituted oxazolines were obtained in good yields with high enantioselectivities.
Iron-catalyzed protodehalogenation of alkyl and aryl halides using hydrosilanes
A simple and efficient iron-catalyzed protodehalogenation of alkyl and aryl halides using phenylhydrosilane is disclosed.
Selective alkyl ether cleavage by cationic bis(phosphine)iridium complexes
Simple cationic bis(phosphine)iridium complexes are shown to be highly selective catalysts for ether cleavage with silanes. Benzylic ethers can be cleaved under mild conditions in the presence of reductively-labile functional groups.
Oxidative cross-dehydrogenative [2 + 3] annulation of α-amino ketones with α-keto esters: concise synthesis of clausenamide analogues
A one-pot oxidative cross-dehydrogenative [2 + 3] annulation of α-amino ketones with α-keto esters at room temperature is reported.
Synthesis of the β-linked GalNAc-Kdo disaccharide antigen of the capsular polysaccharide of Kingella kingae KK01
TfOH-catalyzed glycosylation with D-galactosaminyl N-phenyl trifluoroacetimidate as the donor was developed for the construction of the challenging β-(1 → 5)-linked GalNAc-Kdo disaccharide antigen from Kingella kingae KK01.
Identification of a lysine 4-hydroxylase from the glidobactin biosynthesis and evaluation of its biocatalytic potential
We present the functional characterization of GlbB, a lysine 4-hydroxylase from the glidobactin biosynthetic gene cluster.
Palladium-catalyzed intramolecular carboborylation of 1,3-diene and synthesis of ABCD ring of communesins
A palladium-catalyzed intramolecular carboborylation of 1,3-diene has been developed for the synthesis of iminoindolines with a quaternary carbon centre.
Synthesis of the core structure of phalarine
Two new palladium-catalyzed reactions enabled the synthesis of the core structure of phalarine.
Robust Buchwald–Hartwig amination enabled by ball-milling
An operationally simple mechanochemical method for the Pd catalysed Buchwald–Hartwig amination of arylhalides with secondary amines has been developed using a Pd PEPPSI catalyst system.
Organocatalytic asymmetric Michael/hemiketalization/acyl transfer reaction of 1,3-propanediones with (E)-2-(2-nitrovinyl)phenols
An organocatalytic asymmetric cascade Michael/hemiketalization/acyl transfer reaction between (E)-2-(2-nitrovinyl)phenols and 1,3-propanediones is disclosed to generate products having keto, ester and nitro functionalities.
Highly regioselective α-alkylation of α,β,γ,δ-unsaturated aldehydes
The first regioselective MBH-type α-alkylation of α,β,γ,δ-unsaturated aldehydes is achieved using diarylcarbinols with an excellent E/Z selectivity under mild reaction conditions.
Palladium-catalyzed salt-free double decarboxylative aryl allylation
We describe a palladium catalyzed salt-free decarboxylative aryl allylation of free benzoic acids with allyl tert-butyl-carbonates.
Synthesis of hydrophobic insulin-based peptides using a helping hand strategy
A universal “helping hand” to facilitate the synthesis of A chain of insulin-related peptides.
Total synthesis of incargranine A
Synthetic studies into the origins of the alkaloid incargranine A have resulted in the development of a four-step (longest linear sequence) total synthesis.
Transition state analysis of an enantioselective Michael addition by a bifunctional thiourea organocatalyst
Transition structure for the bifunctional thiourea catalyzed Michael addition using 13C KIEs and DFT calculations.
Selectivity, ligand deconstruction, and cellular activity analysis of a BPTF bromodomain inhibitor
19F NMR-guided development of a BPTF chemical probe through SAR and ligand deconstruction.
Hydroaminoalkylation of sterically hindered alkenes with N,N-dimethyl anilines using a scandium catalyst
Atom-economical and regioselective C(sp3)–C(sp3) bond formation has been achieved by C(sp3)–H alkylation of N,N-dimethyl anilines with sterically demanding alkenes by scandium catalysis.
One-pot stapling of interchain disulfides of antibodies using an isobutylene motif
Stable monoclonal antibodies are generated by the mild and efficient re-bridging of interchain disulfides using an isobutylene motif. Effector functions and pharmacokinetics of the stapled antibodies are maintained at a similar level as their native forms.
Methyl 5-MeO-N-aminoanthranilate, a minimalist fluorogenic probe for sensing cellular aldehydic load
A minimalist fluorogenic probe is presented capable of the mapping of aldehydic load through live cell microscopy.
Protic additives or impurities promote imine reduction with pinacolborane
We report here that addition of stoichiometric amounts of alcohols or water to mixtures of imines and pinacolborane promote reduction reactions.
Investigations into the DNA-binding mode of doxorubicinone
Spectroscopic and calorimetric study of DNA-binding by doxorubicin and doxorubicinone found different binding modes for the two molecules, despite their structural homology.
Self-assembled micro-fibres by oxime connection of linear peptide amphiphiles
The oxime connection between linear peptides and hydrophobic aldehydes affords amphiphiles that are excellent biocompatible scaffolds for the hierarchical self-assembly of nano and micro fibrillar structures in aqueous media.
A hemithioindigo molecular motor for metal surface attachment
We report on the synthesis of a hemithioindigo molecular motor bearing thioether feet for metal surface attachment and a comprehensive study of its light induced unidirectional motion in solution.
Chemoselective reduction of isothiocyanates to thioformamides mediated by the Schwartz reagent
Thioformamides are easily prepared – under full chemocontrol – through the partial reduction of isothiocyanates with the in situ generated Schwartz reagent.
Synthesis and initial biological evaluation of myxocoumarin B
The first total synthesis of myxocoumarin B along with its initial biological evaluation in antifungal and cytotoxicity assays are reported.
Efficiency and fidelity of T3 DNA ligase in ligase-catalysed oligonucleotide polymerisations
T3 and T4 DNA ligase have contrasting performance in ligase-catalysed oligonucleotide polymerisations.
Metal-free photocatalytic thiol–ene/thiol–yne reactions
We report a metal-free photocatalytic approach to the synthesis of glycoconjugates, highlighting the mild nature of the reaction conditions.
Reversibly photoswitchable alkoxy azobenzenes connected benzenetricarboxamide discotic liquid crystals with perpetual long range columnar assembly
Reversibly photoswitchable discotic liquid crystals (DLCs) with no change in columnar assembly.
Sulfur polymer composites as controlled-release fertilisers
A controlled-release fertiliser was prepared by the inverse vulcanisation of canola oil in the presence of nitrogen, phosphorous and potassium nutrients.
Rh-Catalyzed diastereoselective desymmetrization of enone tethered-cyclohexadienones via tandem arylative cyclization
The rhodium-catalyzed arylative cyclization of enone tethered-cyclohexadienones has been developed with high efficiency, thus providing cis-fused bicyclic enones in good yields and with excellent diastereoselectivities.
Understanding the axial chirality control of quinidine-derived ammonium cation-directed O-alkylation: a computational study
DFT calculations reveal the origins of axial chirality control by cinchona alkaloid derivatives.
Regiospecific formal [3 + 2] annulation of tert-propargyl alcohols with acyclic 1,3-diketones via the cycloisomerization of homoallenyl ketones
A one-pot, regiospecific synthesis of dihydrofurans bearing a quaternary centre is developed from the formal [3 + 2] annulation of tert-propargyl alcohols and 1,3-diketones through the SN2I mechanism to form homoallenyl ketone and a subsequent cycloisomerization reaction.
A SNAP-tag fluorogenic probe mimicking the chromophore of the red fluorescent protein Kaede
Structural modulation of the fluorescent protein (FP) chromophore to enable fluorogenic probe for SNAP-tag towards wash-free live cell imaging.
Boronic acid-catalysed C-3 selective ring opening of 3,4-epoxy alcohols with thiophenols and thiols
A boronic acid-catalysed C-3 selective ring opening of 3,4-epoxy alcohols with thiophenols and thiols as nucleophiles has been accomplished.
Sialylated variants of lacto-N-tetraose exhibit antimicrobial activity against Group B Streptococcus
Human milk oligosaccharides (HMOs) possess antimicrobial activity against a number of bacterial pathogens.
Enantioselective syntheses and application of 4-epi-galiellalactone and the corresponding activity-based probe: from strained bicycles to strained tricycles
Efficient syntheses of 4-epi-galiellalactone and the corresponding activity-based probe enabled chemoproteomic studies to reveal the biological targets.
Why do A·T and G·C self-sort? Hückel aromaticity as a driving force for electronic complementarity in base pairing
Computations reveal that the potential for aromaticity gain and loss in nucleobases play key roles in modulating base pairing strengths.
Design, synthesis, and biological evaluation of C7-functionalized DMXAA derivatives as potential human-STING agonists
A strategy to diversely functionalize the C7-position of DMXAA has been developed as a means to discover potential human-STING agonists.
A fast-response and highly specific Si-Rhodamine probe for endogenous peroxynitrite detection in living cells
Peroxynitrite (ONOO−) is involved in a variety of physiological and pathological processes.
Studies on a landscape of perfluoroaromatic-reactive peptides
Diverse peptide sequences and folds promote cysteine arylation.
An elusive thermal [2 + 2] cycloaddition driven by visible light photocatalysis: tapping into strain to access C2-symmetric tricyclic rings
A mild and operationally simple methodology is reported for the synthesis of cyclobutane rings imbedded within a C2-symmetric tricyclic framework.