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Themed collection Organic & Biomolecular Chemistry 10th Anniversary

69 items
Editorial

Welcome to the 10th anniversary issue of Organic & Biomolecular Chemistry

Introducing the 10th anniversary issue of Organic & Biomolecular Chemistry.

Graphical abstract: Welcome to the 10th anniversary issue of Organic & Biomolecular Chemistry
Perspective

Methylthioxylose – a jewel in the mycobacterial crown?

The discovery of methylthioxylose and studies toward understanding its origins and biological roles.

Graphical abstract: Methylthioxylose – a jewel in the mycobacterial crown?
Perspective

Organic reactivity in liquid ammonia

Liquid ammonia is a useful solvent for many organic reactions including aliphatic and nucleophilic substitution reactions and has the potential to replace conventional dipolar aprotic solvents in a range of reactions.

Graphical abstract: Organic reactivity in liquid ammonia
Perspective

“Frustrated Lewis pair” hydrogenations

This perspective article discusses developments of metal-free hydrogenation catalysts derived from “frustrated Lewis pair” (FLP) systems.

Graphical abstract: “Frustrated Lewis pair” hydrogenations
Perspective

Chemical and semisynthesis of posttranslationally modified proteins

Recent advances in chemical and semisynthesis of proteins are becoming increasingly instrumental to prepare homogeneous posttranslationally modified proteins for biochemical and structural analyses. Here, we survey these efforts and their importance in dissecting the role of several posttranslational modifications on various proteins.

Graphical abstract: Chemical and semisynthesis of posttranslationally modified proteins
Perspective

Peptide and peptidomimetic ligands for CXC chemokine receptor 4 (CXCR4)

This perspective article highlights the recent developments of peptide and peptidomimetic ligands for CXC chemokine receptor 4 (CXCR4).

Graphical abstract: Peptide and peptidomimetic ligands for CXC chemokine receptor 4 (CXCR4)
Perspective

A unified access to diverse heteroaromatic scaffolds using the radical chemistry of xanthates

The radical addition of xanthates to alkenes provides a practical and flexible entry to a broad variety of heteroaromatic structures.

Graphical abstract: A unified access to diverse heteroaromatic scaffolds using the radical chemistry of xanthates
Communication

New H-bonding patterns in biphenyl-based synthetic lectins; pyrrolediamine bridges enhance glucose-selectivity

A new synthetic lectin features pyrroles and amines as polar binding units. In aqueous buffer, glucose is bound selectively over all other tested carbohydrates.

Graphical abstract: New H-bonding patterns in biphenyl-based synthetic lectins; pyrrolediamine bridges enhance glucose-selectivity
Communication

Conotoxin engineering: dual pharmacophoric noradrenaline transport inhibitor/integrin binding peptide with improved stability

The synthesis, biological activity and pharmacokinetics of a stable cyclic conotoxin with two independent pharmacophores are described.

Graphical abstract: Conotoxin engineering: dual pharmacophoric noradrenaline transport inhibitor/integrin binding peptide with improved stability
Communication

Sym-(CH2X)5-corannulenes: molecular pentapods displaying functional group and bioconjugate appendages

Pentapodal ω-functional derivatives of corannulene have been synthesized from sym-pentachlorocorannulene by iron-catalyzed aryl–alkyl cross coupling reactions.

Graphical abstract: Sym-(CH2X)5-corannulenes: molecular pentapods displaying functional group and bioconjugate appendages
Communication

Development of strong Brønsted base catalysis: catalytic direct-type Mannich reactions of non-activated esters via a product-base mechanism

A catalytic Mannich reaction of a simple ester with no activating functionality at the α-position via a product-base mechanism was reported.

Graphical abstract: Development of strong Brønsted base catalysis: catalytic direct-type Mannich reactions of non-activated esters via a product-base mechanism
Communication

Self condensation of enamines mediated by acetylation. A novel approach to 1-(azol-5-yl)-(1E,3Z)-butadiene-4-N,N-dimethylamines

Novel self-condensation of 3-(azol-5-yl)-1,1-dimethylenamines has been found to form new C–C bonds leading to 2,4-(1,2,3-triazole-1,2,3-thiadiazole-3-phenylisothiazole)-(1E,3Z)-5-yl-butadiene-1-amines.

Graphical abstract: Self condensation of enamines mediated by acetylation. A novel approach to 1-(azol-5-yl)-(1E,3Z)-butadiene-4-N,N-dimethylamines
Communication

Flow synthesis using gaseous ammonia in a Teflon AF-2400 tube-in-tube reactor: Paal–Knorr pyrrole formation and gas concentration measurement by inline flow titration

Permeation of ammonia through Teflon AF-2400 (which is temperature and solvent dependent) facilitated the continuous flow Paal–Knorr synthesis of pyrroles.

Graphical abstract: Flow synthesis using gaseous ammonia in a Teflon AF-2400 tube-in-tube reactor: Paal–Knorr pyrrole formation and gas concentration measurement by inline flow titration
Communication

Synthesis of 1,2,4-triazines and the triazinoisoquinolinedione DEF ring system of noelaquinone

The intramolecular Staudinger-aza-Wittig reaction was used for the first preparation of the DEF ring system of noelaquinone.

Graphical abstract: Synthesis of 1,2,4-triazines and the triazinoisoquinolinedione DEF ring system of noelaquinone
Communication

Amphiphilic α-helix mimetics based on a benzoylurea scaffold

The design and synthesis of conformationally constrained amphiphilic benzoylurea α-helix mimetics is described.

Graphical abstract: Amphiphilic α-helix mimetics based on a benzoylurea scaffold
Communication

Photochemical oxazolenitrile conversion downstream of rhizoxin biosynthesis and its impact on antimitotic activity

In the endofungal bacterium Burkholderia rhizoxinica novel rhizoxin derivatives with unusual nitrile substitutions are formed by a rare photochemical transformation.

Graphical abstract: Photochemical oxazole–nitrile conversion downstream of rhizoxin biosynthesis and its impact on antimitotic activity
Communication

Selective thioether macrocyclization of peptides having the N-terminal 2-chloroacetyl group and competing two or three cysteine residues in translation

The mode of thioether macrocyclization of peptides containing an N-terminal 2-chloroacetyl group and two or three competing cysteine residues at downstream positions has been extensively studied, leading to a strategy for designated formation of overlapping-bicyclic peptides or dumbbell-type bicyclic peptides.

Graphical abstract: Selective thioether macrocyclization of peptides having the N-terminal 2-chloroacetyl group and competing two or three cysteine residues in translation
Communication

Synthesis and structure–activity relationships of o-sulfonamido-arylhydrazides as inhibitors of LL-diaminopimelate aminotransferase (LL-DAP-AT)

The synthesis of a series of o-sulfonamido-arylhydrazides and their activity as inhibitors of LL-diaminopimelic acid aminotransferase are described.

Graphical abstract: Synthesis and structure–activity relationships of o-sulfonamido-arylhydrazides as inhibitors of ll-diaminopimelate aminotransferase (ll-DAP-AT)
Communication

Facile air-oxidation of large aromatic hydrocarbon bay regions to bay region quinones: predicted oxygen-sensitivity of hydrogen-terminated carbon nanotubes

The ease with which dimesitylbisanthene oxidizes in air to the corresponding bay region quinone is seen as a warning that hydrogen-terminated carbon nanotubes having bay regions on their rims may be highly sensitive to air oxidation.

Graphical abstract: Facile air-oxidation of large aromatic hydrocarbon bay regions to bay region quinones: predicted oxygen-sensitivity of hydrogen-terminated carbon nanotubes
Communication

Short polyglutamine peptide forms a high-affinity binding site for thioflavin-T at the N-terminus

We report the first observation of direct molecular contacts between ThT and model peptide aggregates by applying solid-state NMR spectroscopy.

Graphical abstract: Short polyglutamine peptide forms a high-affinity binding site for thioflavin-T at the N-terminus
Communication

Reactions of triflate esters and triflamides with an organic neutral super-electron-donor

The bis-pyridinylidene 13 converts aliphatic and aryl triflate esters to the corresponding alcohols and phenols respectively, using DMF as solvent, generally in excellent yields.

Graphical abstract: Reactions of triflate esters and triflamides with an organic neutral super-electron-donor
Communication

Convergent diastereoselective preparation of adjacent quaternary stereocenters in an acyclic system

The combined carbometalation–zinc homologation–allylation reaction with ketones allows the preparation of allylic vicinal diol derivatives possessing two adjacent quaternary centers in an acyclic system through the concomitant formation of three new carbon-carbon bonds in a single-pot operation..

Graphical abstract: Convergent diastereoselective preparation of adjacent quaternary stereocenters in an acyclic system
Communication

Tuning and predicting biological affinity: aryl nitriles as cysteine protease inhibitors

The influence of the electrophilicity of aromatic nitriles on cysteine protease inhibition and cytotoxicity was investigated. Calculations were used to obtain nitrile electrophilicities, revealing a clear correlation with biological affinity.

Graphical abstract: Tuning and predicting biological affinity: aryl nitriles as cysteine protease inhibitors
Communication

Observation of neighboring ortho-hydroxyl group participation in organocatalytic asymmetric sequential Michael-lactonization reactions: synthesis of highly substituted chiral spirodihydrocoumarins

A general approach to the asymmetric synthesis of spirodihydrocoumarins with a quaternary stereocenter was achieved through a favoured 21-membered supramolecular transition state using sequential Michael and lactonization reactions.

Graphical abstract: Observation of neighboring ortho-hydroxyl group participation in organocatalytic asymmetric sequential Michael-lactonization reactions: synthesis of highly substituted chiral spirodihydrocoumarins
Communication

A general electron transfer reduction of lactones using SmI2–H2O

A selective method for the reduction of lactones of all ring sizes and topologies using SmI2–H2O and a Lewis base is described.

Graphical abstract: A general electron transfer reduction of lactones using SmI2–H2O
Communication

The direct catalytic asymmetric aldol reaction of α-substituted nitroacetates with aqueous formaldehyde under base-free neutral phase-transfer conditions

Enantioselective direct aldol reaction of α-substituted nitroacetates with aqueous formaldehyde has been achieved under base-free neutral phase-transfer conditions.

Graphical abstract: The direct catalytic asymmetric aldol reaction of α-substituted nitroacetates with aqueous formaldehyde under base-free neutral phase-transfer conditions
Communication

Water-soluble, deep-red fluorescent squaraine rotaxanes

Squaraine rotaxanes with four large stopper groups attached to the ends of the encapsulated squaraine are excellent fluorescent tracers with rapid renal clearance and very low tissue uptake in living mice.

Graphical abstract: Water-soluble, deep-red fluorescent squaraine rotaxanes
Paper

Chemoselective Staudinger-phosphite reaction of symmetrical glycosyl-phosphites with azido-peptides and polygycerols

In this paper we present the synthesis of glyco-phosphoramidate conjugates as easily accessible analogs of glyco-phosphorous esters via the Staudinger-phosphite reaction.

Graphical abstract: Chemoselective Staudinger-phosphite reaction of symmetrical glycosyl-phosphites with azido-peptides and polygycerols
Paper

Reactive intermediates in the H-phosphonate synthesis of oligonucleotides

The formation of H-phosphonate diesters is an important step in the synthesis of oligonucleotides.

Graphical abstract: Reactive intermediates in the H-phosphonate synthesis of oligonucleotides
Paper

Ionization state of the catalytic dyad Asp25/25′ in the HIV-1 protease: NMR studies of site-specifically 13C labelled HIV-1 protease prepared by total chemical synthesis

Total chemical synthesis was used to site-specifically 13C-label active site Asp25 and Asp25′ residues in HIV-1 protease and in several chemically synthesized analogues of the enzyme molecule.

Graphical abstract: Ionization state of the catalytic dyad Asp25/25′ in the HIV-1 protease: NMR studies of site-specifically 13C labelled HIV-1 protease prepared by total chemical synthesis
Paper

Formation of luminescent terbium(III) self-assemblies from pyridyl bis-amidothioureas based ligands in MeOH and in water–DMSO solutions and their use in anion sensing application

The self-assembly formation between the bis amidothiourea ligands 1 and 2 with Tb(III) is described. These give rise to Tb(III) centred emission which is affected upon binding of these to anions such as acetate and phosphate.

Graphical abstract: Formation of luminescent terbium(iii) self-assemblies from pyridyl bis-amidothioureas based ligands in MeOH and in water–DMSO solutions and their use in anion sensing application
Paper

New parasite inhibitors encompassing novel conformationally-locked 5′-acyl sulfamoyl adenosines

3′-endo-Sugar-locked 5′-acyl sulfamoyl adenosines inhibit Trypanosoma and Leishmania with IC50s of 0.25–0.51 μM.

Graphical abstract: New parasite inhibitors encompassing novel conformationally-locked 5′-acyl sulfamoyl adenosines
Paper

Vinyl-triphenylamine dyes, a new family of switchable fluorescent probes for targeted two-photon cellular imaging: from DNA to protein labeling

A new family of nonlinear fluorescent probes for specific DNA or protein labeling was designed by structure space exploration around the vinyl-triphenylamine core.

Graphical abstract: Vinyl-triphenylamine dyes, a new family of switchable fluorescent probes for targeted two-photon cellular imaging: from DNA to protein labeling
Paper

Synthesis of isoxazoles en route to semi-aromatized polyketides: dehydrogenation of benzonitrile oxidepara-quinone acetal cycloadducts

A facile access has been developed to highly functionalized polycyclic isoxazoles, suitable intermediates for the synthesis of semi-aromatized polyketides, via a two-step protocol including regioselective 1,3-dipolar cycloaddition and MnO2-mediated dehydrogenation.

Graphical abstract: Synthesis of isoxazoles en route to semi-aromatized polyketides: dehydrogenation of benzonitrile oxide–para-quinone acetal cycloadducts
Paper

Helical self-assembly and co-assembly of fluorinated, preorganized discotics

Fluorinated bipyridine discotics self-assemble into stable helical columnar mesophases and alternating helical assemblies with hydrocarbon bipyridine discotics in fluorinated media.

Graphical abstract: Helical self-assembly and co-assembly of fluorinated, preorganized discotics
Paper

Preferential extraction of left- or right-handed single-walled carbon nanotubes by use of chiral diporphyrin nanotweezers

The 2,6-pyridylene-bridged chiral diporphyrin nanotweezers recognise handedness and diameter of SWNTs simultaneously and independently, yielding optically active SWNTs with narrow diameter range.

Graphical abstract: Preferential extraction of left- or right-handed single-walled carbon nanotubes by use of chiral diporphyrin nanotweezers
Paper

Efficient proline and prolinol ether mediated 3-component synthesis of 3- and 3,4-substituted chromenone derivatives

A highly efficient one-pot synthesis of valuable 3,4-substituted chromenone derivatives by the reaction of 1,3-diketones with aldehydes in the presence of L-proline was developed. Chiral 3-substituted chromenones are obtained with high enantioselectivities when a chiral diarylprolinol TMS-ether is applied in the reaction.

Graphical abstract: Efficient proline and prolinol ether mediated 3-component synthesis of 3- and 3,4-substituted chromenone derivatives
Paper

[2]Pseudorotaxanes, [2]rotaxanes and metal–organic rotaxane frameworks containing tetra-substituted dibenzo[24]crown-8 wheels

[2]Pseudorotaxanes, [2]rotaxanes and metal–organic rotaxane framework materials are prepared that utilise symmetrical DB24C8 analogues containing four CH2OR (R = CH2CH2CH3, CH2(C6H5), C6H5 and C6H4(4-COOEt)) substituents on the 4 and 5 positions of the aromatic rings.

Graphical abstract: [2]Pseudorotaxanes, [2]rotaxanes and metal–organic rotaxane frameworks containing tetra-substituted dibenzo[24]crown-8 wheels
Paper

Steric desolvation enhances the effective molarities of intramolecular H-bonding interactions

Effective molarities for intramolecular phosphonate diester-phenol H-bonds vary with solvent indicating that changes in the solvation shell can make a significant contribution to the stability of a supramolecular complex.

Graphical abstract: Steric desolvation enhances the effective molarities of intramolecular H-bonding interactions
Paper

Synthesis of selective inhibitors against V. cholerae sialidase and human cytosolic sialidase NEU2

Two inhibitors with selectivity against V. cholerae sialidase and human cytosolic sialidase NEU2, respectively, were identified.

Graphical abstract: Synthesis of selective inhibitors against V. cholerae sialidase and human cytosolic sialidase NEU2
Paper

The role of cyclobutenes in gold(I)-catalysed skeletal rearrangement of 1,6-enynes

A bicyclo[3.2.0]hept-5-ene formed in good yield in a gold(I)-catalysed reaction, has been structurally characterised.

Graphical abstract: The role of cyclobutenes in gold(i)-catalysed skeletal rearrangement of 1,6-enynes
Paper

Dipicolylamine as a unique structural switching element for helical peptides

A simple method for on-resin synthesis of dipicolylamine (Dpa)-containing peptides was developed, which enables the design of a unique metal-responsive peptide.

Graphical abstract: Dipicolylamine as a unique structural switching element for helical peptides
Paper

Desymmetrizing reductive aldol cyclizations of enethioate derivatives of 1,3-diones catalyzed by a chiral copper hydride

Enethioate derivatives of prochiral 1,3-diones underwent desymmetrizing catalytic reductive aldol cyclizations to furnish β-hydroxythioesters with >98 : 2 dr, up to 94% yield and 98% ee.

Graphical abstract: Desymmetrizing reductive aldol cyclizations of enethioate derivatives of 1,3-diones catalyzed by a chiral copper hydride
Paper

Porphyrin dyads linked by a rotatable 3,3′-biphenyl scaffold: a new binding motif for small ditopic molecules

The complexation behaviour of a new bis-porphyrin bearing a rotatable linker with diaza-ligands has been studied. Featuring a semi-flexible biphenyl linkage, these bis-porphyrin systems are capable of reversible binding to small ditopic molecules, opening up the possibility of developing a new generation of chemoswitchable systems.

Graphical abstract: Porphyrin dyads linked by a rotatable 3,3′-biphenyl scaffold: a new binding motif for small ditopic molecules
Paper

Synthesis of a 3-deoxy-D-manno-octulosonic acid (KDO) building block from D-glucose via fermentation

A 3-deoxy-D-manno-octulosonic acid (KDO) building block was made starting from glucose through pathway engineering of Escherichia coli and subsequent chemical modifications to provide an alternative method to produce KDO, usually found in plant and bacterial oligosaccharides.

Graphical abstract: Synthesis of a 3-deoxy-d-manno-octulosonic acid (KDO) building block from d-glucose via fermentation
Paper

The stereocontrolled total synthesis of spirastrellolide A methyl ester. Fragment coupling studies and completion of the synthesis

The first total synthesis of (+)-spirastrellolide A methyl ester was achieved based on the sequential coupling of four fragments and a remarkably high yielding macrolactonisation. A series of simplified analogues of spirastrellolide incorporating the C26–C47 region were also prepared by π-allyl Stille coupling reactions.

Graphical abstract: The stereocontrolled total synthesis of spirastrellolide A methyl ester. Fragment coupling studies and completion of the synthesis
Paper

The stereocontrolled total synthesis of spirastrellolide A methyl ester. Expedient construction of the key fragments

A modular strategy for the synthesis of the antimitotic marine macrolide spirastrellolide A methyl ester was adopted based on the envisaged sequential coupling of a series of four suitably functionalised fragments.

Graphical abstract: The stereocontrolled total synthesis of spirastrellolide A methyl ester. Expedient construction of the key fragments
Paper

Amphiphilic dynamic NDI and PDI probes: imaging microdomains in giant unilamellar vesicles

Dynamic amphiphiles with fluorescent naphthalenediimide tails can be used to label membrane microdomains and activate DNA as transporters in lipid bilayers.

Graphical abstract: Amphiphilic dynamic NDI and PDI probes: imaging microdomains in giant unilamellar vesicles
Paper

Synthesis and evaluation of new polyenic compounds as potential PPARs modulators

In order to identify new leads for the treatment of type 2 diabetes, polyenic molecules A and B derived from nipecotic acid and dienol derivatives C have been prepared and their effect on PPARs transcriptional activity evaluated and compared to that of rosiglitazone, WY14,643 and GW501516.

Graphical abstract: Synthesis and evaluation of new polyenic compounds as potential PPARs modulators
Paper

Substituent effects on axle binding in amide pseudorotaxanes: comparison of NMR titration and ITC data with DFT calculations

Guest discrimination: NMR titration and ITC experiments were used to examine the binding behavior of differently disubstituted diamide guests to a tetralactam macrocycle.

Graphical abstract: Substituent effects on axle binding in amide pseudorotaxanes: comparison of NMR titration and ITC data with DFT calculations
Paper

Multimodal fluorescence modulation using molecular photoswitches and upconverting nanoparticles

Different wavelengths of light can be used to selectively quench the emission from upconverting nanoparticles depending on the isomeric state of photoswitches decorated onto their surfaces.

Graphical abstract: Multimodal fluorescence modulation using molecular photoswitches and upconverting nanoparticles
Paper

Combined experimental and theoretical studies on the photophysical properties of cycloparaphenylenes

Absorption and fluorescence in solution/solid states. High fluorescence quantum yields. Assignment of UV-vis absorption. Explanation of unique HOMO–LUMO behaviour.

Graphical abstract: Combined experimental and theoretical studies on the photophysical properties of cycloparaphenylenes
Paper

Peptides that anneal to natural collagen in vitro and ex vivo

Collagen mimetic peptides bind tightly to mammalian collagen in vitro and ex vivo, providing a new modality for wound care.

Graphical abstract: Peptides that anneal to natural collagen in vitro and ex vivo
Paper

On the origins of diastereoselectivity in the conjugate additions of the antipodes of lithium N-benzyl-(N-α-methylbenzyl)amide to enantiopure cis- and trans-dioxolane containing α,β-unsaturated esters

Classical doubly diastereoselective “matching” and “mismatching” effects are not observed upon conjugate addition of the antipodes of lithium N-benzyl-(N-α-methylbenzyl)amide to tert-butyl (E)-4,5-O-isopropylidene-4,5-dihydroxyhex-2-enoates.

Graphical abstract: On the origins of diastereoselectivity in the conjugate additions of the antipodes of lithium N-benzyl-(N-α-methylbenzyl)amide to enantiopure cis- and trans-dioxolane containing α,β-unsaturated esters
Paper

Structure, stereochemistry and synthesis of enantiopure cyclohexenone cis-diol bacterial metabolites derived from phenols

Biotransformation of 3- and 2,5-substituted phenols yielded enantiopure cyclohexenone cis-diols; ECD spectroscopy, X-ray crystallography and stereochemical correlation was used to establish absolute configurations.

Graphical abstract: Structure, stereochemistry and synthesis of enantiopure cyclohexenone cis-diol bacterial metabolites derived from phenols
Paper

Construction of multi-component supramolecular architectures of bile acids and cinchona alkaloids through helical-pitch-synchronized crystallization

Multi-component organic crystals containing different kinds of helical motifs were constructed based on bile acids and cinchona alkaloids.

Graphical abstract: Construction of multi-component supramolecular architectures of bile acids and cinchona alkaloids through helical-pitch-synchronized crystallization
Paper

Remote stereocontrol in reactions between 4- and 5-alkoxyalk-2-enylstannanes and 1-alkoxycarbonylimines and analogues: stereoselective approaches to novel α-amino acids

Reactions of the allyltin trichlorides generated from (4S)-4-benzyloxypent-2-enyl(tributyl)stannane and analogous stannanes with imines prepared from glyoxalates proceed with useful levels of 1,5-stereocontrol; modest 1,6-stereocontrol was observed using 5-hydroxy- and 5-methoxy-hex-2-enylstannanes.

Graphical abstract: Remote stereocontrol in reactions between 4- and 5-alkoxyalk-2-enylstannanes and 1-alkoxycarbonylimines and analogues: stereoselective approaches to novel α-amino acids
Paper

Combined coinage metal catalysis in natural product synthesis: total synthesis of (+)-varitriol and seven analogs

The combined use of the coinage metals copper and gold allows an efficient stereoselective synthesis of (+)-varitriol and various analogs.

Graphical abstract: Combined coinage metal catalysis in natural product synthesis: total synthesis of (+)-varitriol and seven analogs
Paper

Platinum catalyzed 7-endo cyclization of internal alkynyl amides and its application to synthesis of the caprazamycin core

Considering the synthesis of the caprazamycin core, the scope and limitations of platinum catalyzed 7-endo cyclization of internal alkynyl amides were disclosed.

Graphical abstract: Platinum catalyzed 7-endo cyclization of internal alkynyl amides and its application to synthesis of the caprazamycin core
Paper

Probing riboswitch–ligand interactions using thiamine pyrophosphate analogues

The binding of thiamine pyrophosphate (TPP) to the thiM riboswitch has been systematically explored by testing a range of TPP analogues in which the aminopyrimidine ring, the central thiazolium ring, and the pyrophosphate tail are each replaced in turn by similar structures.

Graphical abstract: Probing riboswitch–ligand interactions using thiamine pyrophosphate analogues
Paper

Design, synthesis and biological evaluation of non-natural modulators of quorum sensing in Pseudomonas aeruginosa

Novel potent antagonists of quorum sensing in Pseudomonas aeruginosa are reported, which strongly inhibit the production of virulence factors.

Graphical abstract: Design, synthesis and biological evaluation of non-natural modulators of quorum sensing in Pseudomonas aeruginosa
Paper

Synthetic studies towards the mulberry Diels–Alder adducts: H-bond accelerated cycloadditions of chalcones

The methyl ether derivatives of a number of mulberry Diels–Alder adducts have been synthesized by a thermal [4 + 2]-cycloaddition reaction between a chalcone and dehydroprenyl diene. A H-bonded ortho OH substituent on the chalcone was found to be essential for Diels–Alder reactivity and the experimental results were supported by density functional theory calculations.

Graphical abstract: Synthetic studies towards the mulberry Diels–Alder adducts: H-bond accelerated cycloadditions of chalcones
Paper

Solvent and substituent effects on aggregation constants of perylene bisimide π-stacks – a linear free energy relationship analysis

In this article we have intensively addressed the question how solvents effect the aggregation strength of perylene bisimides.

Graphical abstract: Solvent and substituent effects on aggregation constants of perylene bisimide π-stacks – a linear free energy relationship analysis
Paper

Enantioselective synthesis of 2,5-dihydrobenzo[b]azepine derivatives via iridium-catalyzed asymmetric allylic amination with 2-allylanilines and ring-closing-metathesis reaction

Iridium-catalyzed asymmetric allylic amination of allylic carbonates with 2-allylanilines and ring-closing-metathesis reaction provided highly enantioenriched 2,5-dihydrobenzo[b]azepine derivatives.

Graphical abstract: Enantioselective synthesis of 2,5-dihydrobenzo[b]azepine derivatives via iridium-catalyzed asymmetric allylic amination with 2-allylanilines and ring-closing-metathesis reaction
Paper

α-N-Linked glycopeptides: conformational analysis and bioactivity as lectin ligands

NMR and modelling give new insights on the molecular recognition of unnatural α-Gal-N-linked glycopeptides by lectins.

Graphical abstract: α-N-Linked glycopeptides: conformational analysis and bioactivity as lectin ligands
Paper

Chemoselective cyclization of unprotected linear peptides by α-ketoacid–hydroxylamine amide-ligation

Peptides with an N-terminal nitrone and a C-terminal α-ketoacid undergo chemoselective cyclizations without reagents and in the presence of unprotected side chains. The precursors are prepared by Fmoc-SPPS.

Graphical abstract: Chemoselective cyclization of unprotected linear peptides by α-ketoacid–hydroxylamine amide-ligation
Paper

Double stranded polymeric ladderphanes with 16-π-electron antiaromatic metallocycle linkers

Three double stranded polymeric ladderphanes with 16-π-electron antiaromatic metallocycle linkers are synthesised by ring opening metathesis polymerisation of the corresponding bisnorbornene monomers.

Graphical abstract: Double stranded polymeric ladderphanes with 16-π-electron antiaromatic metallocycle linkers
Paper

Enantioselective synthesis of C-linked spiroacetal-triazoles as privileged natural product-like scaffolds

The union of the biologically privileged 6,6-spiroacetal scaffold with azides by the regioselective Copper-Catalysed Azide–Alkyne Cycloaddition (CuAAC) affords novel C-linked spiroacetal-triazoles. The anomeric C-linkage is anticipated to provide increased stability towards hydrolytic cleavage.

Graphical abstract: Enantioselective synthesis of C-linked spiroacetal-triazoles as privileged natural product-like scaffolds
Paper

Benzimidazole-based anion receptors: tautomeric switching and selectivity

Tautomeric switching is observed in a series of benzimidazole-based anion receptors upon addition of basic anions.

Graphical abstract: Benzimidazole-based anion receptors: tautomeric switching and selectivity
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