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Themed collection Organic & Biomolecular Chemistry HOT article collection

40 items
Perspective

From pirates and killers: does metabolite diversity drive bacterial competition?

This article discusses interspecies competition by sets of closely related metabolites with significantly different biological activities.

Graphical abstract: From pirates and killers: does metabolite diversity drive bacterial competition?
Review Article

Progress in the synthesis of fluorinated phosphatidylcholines for biological applications

Fluorinated phospholipids have attracted a lot of interest over the past 40 years. While mono- and polyfluorinated analogs are mostly designed to be used as 19F NMR probes, highly fluorinated phospholipids are mainly developed as drug delivery devices and oxygen carriers. This review describes their synthetic pathways, their properties and potential applications.

Graphical abstract: Progress in the synthesis of fluorinated phosphatidylcholines for biological applications
Review Article

Transient imines as ‘next generation’ directing groups for the catalytic functionalisation of C–H bonds in a single operation

This review describes recent developments in the use of catalytic transient directing groups, through imine linkages, which in combination with transition metal catalysts provide streamlined C–H functionalisation processes.

Graphical abstract: Transient imines as ‘next generation’ directing groups for the catalytic functionalisation of C–H bonds in a single operation
Review Article

Review of synthetic approaches toward maoecrystal V

Synthetic approaches toward the complex natural product diterpenoid maoecrystal V are reviewed, including successful total syntheses, published synthetic efforts, and efforts compiled from dissertations.

Graphical abstract: Review of synthetic approaches toward maoecrystal V
Review Article

Chiral proton-transfer shuttle catalysts for carbene insertion reactions

The development of chiral proton-transfer shuttles provides a totally new enantiocontrol strategy for transition metal-catalyzed asymmetric carbene insertion reactions.

Graphical abstract: Chiral proton-transfer shuttle catalysts for carbene insertion reactions
Review Article

The Piancatelli reaction and its variants: recent applications to high added-value chemicals and biomass valorization

The conversion of furfuryl alcohols by the Piancatelli reaction (and its C- and N-variants) provided highly functionalized cyclopentenones (intermolecular) and spirocycles (intramolecular).

Graphical abstract: The Piancatelli reaction and its variants: recent applications to high added-value chemicals and biomass valorization
Review Article

Catalytic asymmetric enamine protonation reaction

Recent advances in catalytic enantioselective enamine protonation for the synthesis of optically active carbonyl compounds are summarized in this review.

Graphical abstract: Catalytic asymmetric enamine protonation reaction
Communication

Two-step activity-based protein profiling of diacylglycerol lipase

Diacylglycerol lipases (DAGL) produce the endocannabinoid 2-arachidonoylglycerol, a key modulator of neurotransmitter release.

Graphical abstract: Two-step activity-based protein profiling of diacylglycerol lipase
From the themed collection: Chemical biology in OBC
Communication

Deletion of a global regulator LaeB leads to the discovery of novel polyketides in Aspergillus nidulans

By disruption of LaeB, a global regulator recently characterized in Aspergillus nidulans, eight cryptic compounds in the mutant were identified, including seven polyketides and one NRPS-like product.

Graphical abstract: Deletion of a global regulator LaeB leads to the discovery of novel polyketides in Aspergillus nidulans
Communication

Electrochemical Hofmann rearrangement mediated by NaBr: practical access to bioactive carbamates

An electrochemical Hofmann rearrangement is reported, which provides general and practical access to bioactive carbamates.

Graphical abstract: Electrochemical Hofmann rearrangement mediated by NaBr: practical access to bioactive carbamates
Communication

Chiral NHC-catalyzed 1,3-dipolar [3 + 2] cycloaddition of azomethine imines with α-chloroaldehydes for the synthesis of bicyclic pyrazolidinones

An NHC-catalyzed [3 + 2] cycloaddition reaction of azomethine imines and α-chloroaldehydes was developed for the synthesis of chiral bicyclic pyrazolidinone derivatives.

Graphical abstract: Chiral NHC-catalyzed 1,3-dipolar [3 + 2] cycloaddition of azomethine imines with α-chloroaldehydes for the synthesis of bicyclic pyrazolidinones
From the themed collection: Synthetic methodology in OBC
Communication

Tuning the fluorescence of tetraphenylethylene in dilute solutions via modulating multiple-hydrogen-bonding interactions between a Hamilton receptor and cyanuric acid

A hydrogen bonded luminescent supramolecular network from HTPE and CTPE can be further tuned.

Graphical abstract: Tuning the fluorescence of tetraphenylethylene in dilute solutions via modulating multiple-hydrogen-bonding interactions between a Hamilton receptor and cyanuric acid
Communication

Synthesis of the [7-5-5] tricyclic core of Daphniphyllum alkaloids

The [7-5-5] tricyclic core of the Daphniphyllum alkaloids was constructed, featuring a Claisen-Ireland rearrangement to install the two contiguous stereogenic centers, E1cB elimination to form the tetrasubstituted C–C double bond, and a 2,3-Wittig rearrangement to construct the quaternary carbon.

Graphical abstract: Synthesis of the [7-5-5] tricyclic core of Daphniphyllum alkaloids
Communication

In vivo and in vitro identification of Z-BOX C – a new bilirubin oxidation end product

A new bilirubin degradation end product was isolated and characterized.

Graphical abstract: In vivo and in vitro identification of Z-BOX C – a new bilirubin oxidation end product
Communication

A concise total synthesis of cochlearoid B

A T-type calcium channel inhibiting natural product cochlearoid B was synthesized in 7 linear steps.

Graphical abstract: A concise total synthesis of cochlearoid B
Open Access Communication

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.

Graphical abstract: Total synthesis of incargranine A
From the themed collection: New Talent
Open Access Communication

Anion transport by ortho-phenylene bis-ureas across cell and vesicle membranes

These simple bis-ureas are found to be powerful anionophores in synthetic vesicles, and also in a live cell assay employing yellow fluorescent protein.

Graphical abstract: Anion transport by ortho-phenylene bis-ureas across cell and vesicle membranes
Paper

Tracking down protein–protein interactions via a FRET-system using site-specific thiol-labeling

A novel Cys-specific bioorthogonalized linker was synthesized and applied in combination with bioorthogonally applicable fluorescent markers to track down protein–protein (p38-MK2) interactions by FRET.

Graphical abstract: Tracking down protein–protein interactions via a FRET-system using site-specific thiol-labeling
Paper

Divergent biosynthesis of indole alkaloids FR900452 and spiro-maremycins

FR900452 was demonstrated to be biosynthesized by the gene cluster of maremycin G and diversified by SnoaL-like protein MarP.

Graphical abstract: Divergent biosynthesis of indole alkaloids FR900452 and spiro-maremycins
Paper

Peripheral cyclic β-amino acids balance the stability and edge-protection of β-sandwiches

cis-2-Aminocyclohexanecarboxylic acid replacements at the edges of β-sandwiches reduce β-sheet propensities just enough to prevent aggregation but still maintain a compact structure.

Graphical abstract: Peripheral cyclic β-amino acids balance the stability and edge-protection of β-sandwiches
From the themed collection: Chemical biology in OBC
Open Access Paper

Synthetic antibody protein mimics of infliximab by molecular scaffolding on novel CycloTriVeratrilene (CTV) derivatives

Downsizing of antibodies: molecular construction of chemo-synthetic antibodies of infliximab by scaffolding of three CDR loops yields synthetic antibodies binding hTNFα.

Graphical abstract: Synthetic antibody protein mimics of infliximab by molecular scaffolding on novel CycloTriVeratrilene (CTV) derivatives
From the themed collection: Chemical biology in OBC
Open Access Paper

Stereoselective synthesis of 2,6-trans-4-oxopiperidines using an acid-mediated 6-endo-trig cyclisation

An acid-mediated 6-endo-trig cyclisation has been developed for the synthesis of trans-6-alkyl-2-methyl-4-oxopiperidines and used for the stereoselective preparation of quinolizidine alkaloid, (+)-myrtine and the piperidine alkaloid, (−)-solenopsin A.

Graphical abstract: Stereoselective synthesis of 2,6-trans-4-oxopiperidines using an acid-mediated 6-endo-trig cyclisation
Paper

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.

Graphical abstract: An elusive thermal [2 + 2] cycloaddition driven by visible light photocatalysis: tapping into strain to access C2-symmetric tricyclic rings
From the themed collection: New Talent
Paper

Synthesis of substituted piperidines by enantioselective desymmetrizing intramolecular aza-Michael reactions

An organocatalytic enantioselective intramolecular aza-Michael reaction has been described for the first time in a desymmetrization process employing substrates different from cyclohexadienones.

Graphical abstract: Synthesis of substituted piperidines by enantioselective desymmetrizing intramolecular aza-Michael reactions
Paper

Diastereo- and enantioselective Mannich/cyclization cascade reaction of isocyanoacetates with cyclic sulfamide ketimines by cinchona alkaloid squaramide/AgOAc cooperative catalysis

This reaction provides facile access to a variety of optically active imidazoline-fused sulfahydantoin derivatives in excellent yields and good to excellent stereoselectivities.

Graphical abstract: Diastereo- and enantioselective Mannich/cyclization cascade reaction of isocyanoacetates with cyclic sulfamide ketimines by cinchona alkaloid squaramide/AgOAc cooperative catalysis
Paper

Hypermonins A and B, two 6-norpolyprenylated acylphloroglucinols with unprecedented skeletons from Hypericum monogynum

Hypermonins A and B, two novel 6-norpolycyclic polyprenylated acylphloroglucinols (PPAPs), were isolated from the leaves and twigs of Hypericum monogynum.

Graphical abstract: Hypermonins A and B, two 6-norpolyprenylated acylphloroglucinols with unprecedented skeletons from Hypericum monogynum
Paper

Dynamic kinetic resolution of biaryl atropisomers by chiral dialkylaminopyridine catalysts

Dynamic kinetic resolutions of atropisomers using chiral DMAPs with fluxional chirality.

Graphical abstract: Dynamic kinetic resolution of biaryl atropisomers by chiral dialkylaminopyridine catalysts
Paper

Expanding antibiotic chemical space around the nidulin pharmacophore

Reinvestigating antibiotic scaffolds that were identified during the Golden Age of antibiotic discovery, but have long since been “forgotten”, has proven to be an effective strategy for delivering next-generation antibiotics capable of combatting multidrug-resistant superbugs.

Graphical abstract: Expanding antibiotic chemical space around the nidulin pharmacophore
Paper

Synthesis of plasmodione metabolites and 13C-enriched plasmodione as chemical tools for drug metabolism investigation

A 10-step synthesis of the antimalarial lead, 13C18-enriched plasmodione, and of seven putative metabolites is described.

Graphical abstract: Synthesis of plasmodione metabolites and 13C-enriched plasmodione as chemical tools for drug metabolism investigation
Paper

Synthetic polyprenol-pyrophosphate linked oligosaccharides are efficient substrates for mycobacterial galactan biosynthetic enzymes

Synthetic glycosyl polyprenol phosphates are substrates for enzymes required for cell wall assembly in mycobacteria, including the organism that causes tuberculosis.

Graphical abstract: Synthetic polyprenol-pyrophosphate linked oligosaccharides are efficient substrates for mycobacterial galactan biosynthetic enzymes
Paper

High efficiency two-photon uncaging coupled by the correction of spontaneous hydrolysis

DNI-Glu proved to be several times more efficient, than MNI-Glu and other analogues.

Graphical abstract: High efficiency two-photon uncaging coupled by the correction of spontaneous hydrolysis
Paper

Asymmetric synthesis of trans-4,5-disubstituted γ-butyrolactones involving a key allylboration step. First access to (−)-nicotlactone B and (−)-galbacin

A new approach based on one-pot sequential transformations with application for the first total synthesis of (−)-nicotlactone B and (−)-galbacin.

Graphical abstract: Asymmetric synthesis of trans-4,5-disubstituted γ-butyrolactones involving a key allylboration step. First access to (−)-nicotlactone B and (−)-galbacin
Paper

An efficient synthesis of 16H-dibenzo[2,3:6,7][1,4]oxazepino[5,4-b]quinazolin-16-ones via an Ullmann reaction catalyzed by CuI

16H-Dibenzo[2,3:6,7][1,4]oxazepino[5,4-b]quinazolin-16-ones were obtained from the available reactants 2-amino-N-(2-hydroxyphenyl)benzamide and 2-bromobenzaldehyde via an Ullmann reaction catalyzed by CuI.

Graphical abstract: An efficient synthesis of 16H-dibenzo[2,3:6,7][1,4]oxazepino[5,4-b]quinazolin-16-ones via an Ullmann reaction catalyzed by CuI
Paper

Small-molecule anticancer agents kill cancer cells by harnessing reactive oxygen species in an iron-dependent manner

In the course of generating a library of open-chain epothilones, we discovered a new class of small molecule anticancer agents that has no effect on tubulin but instead kills selected cancer cell lines by harnessing reactive oxygen species in an iron-dependent manner.

Graphical abstract: Small-molecule anticancer agents kill cancer cells by harnessing reactive oxygen species in an iron-dependent manner
Paper

Supramolecular chiroptical switching of helical-sense preferences through the two-way intramolecular transmission of a single chiral source

Complexation-induced reversal of helical-sense preferences is demonstrated with a simple molecule with a pair of exciton-coupled chromophores.

Graphical abstract: Supramolecular chiroptical switching of helical-sense preferences through the two-way intramolecular transmission of a single chiral source
Paper

EZ isomerization in Suzuki cross-couplings of haloenones: ligand effects and evidence for a separate catalytic cycle

We present evidence for a palladocyclic enolate-like pathway for isomerization of enones occurring during Suzuki cross-coupling reactions.

Graphical abstract: E–Z isomerization in Suzuki cross-couplings of haloenones: ligand effects and evidence for a separate catalytic cycle
Paper

Nickel-catalyzed cross-coupling of β-carbonyl alkenyl pivalates with arylzinc chlorides

The reaction of β-carbonyl alkenyl pivalates with arylzinc reagents was carried out via nickel-catalyzed C–O bond cleavage, forming 3-aryl-substituted α,β-unsaturated carbonyl compounds in moderate to excellent yields.

Graphical abstract: Nickel-catalyzed cross-coupling of β-carbonyl alkenyl pivalates with arylzinc chlorides
Paper

A semi-rigid isoindoline-derived nitroxide spin label for RNA

The new semi-rigid spin label ImUm showed limited motion in RNA duplexes and accurate distances between two spin labels in RNA duplexes were obtained by pulsed EPR spectroscopy.

Graphical abstract: A semi-rigid isoindoline-derived nitroxide spin label for RNA
Paper

Formal total synthesis of salvianolic acid N

Salvianolic acid N was synthesized starting from 3,4-dimethoxybenzaldehyde in 11 steps and with an overall yield of 11%. The key reaction steps were the Wittig reaction for Z-stereoselectivity, the copper catalyzed intramolecular cyclization for seven membered ring skeleton, and the deprotected allylic group with Pd catalysis.

Graphical abstract: Formal total synthesis of salvianolic acid N
Paper

Kinetic basis for the activation of human cyclooxygenase-2 rather than cyclooxygenase-1 by nitric oxide

Kinetic basis for the activation of human cyclooxygenase-2 by nitric oxide.

Graphical abstract: Kinetic basis for the activation of human cyclooxygenase-2 rather than cyclooxygenase-1 by nitric oxide
40 items

About this collection

This on-going collection features all the articles published in Organic & Biomolecular Chemistry in 2018 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!

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