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Themed collection 2017 Hot Articles in Organic and Biomolecular Chemistry

54 articles
Perspective

Evolution inspired engineering of antibiotic biosynthesis enzymes

Chimeragenesis is an effective tool to probe the structure/function relationships of proteins without high-throughput screening systems. Here the proof-of-principle is presented with three pairs of proteins.

Graphical abstract: Evolution inspired engineering of antibiotic biosynthesis enzymes
Review Article

Targeting heparin and heparan sulfate protein interactions

Heparan sulfate is ubiquitously expressed on the cell surface and in the extracellular matrix of all animal cells. These negatively-charged carbohydrate chains play essential roles in many important cellular functions by interacting with various heparan sulfate binding proteins (HSBP). This review discusses methods for targeting these complex biomolecules, as strategies for treating human disease.

Graphical abstract: Targeting heparin and heparan sulfate protein interactions
Review Article

Recent advances in N-heterocyclic carbene catalyzed achiral synthesis

This review reveals the recent developments in NHC-promoted non-asymmetric umpolung transformations resulting in the expeditious construction of versatile achiral natural heterocycles, carbocycles and acylated products.

Graphical abstract: Recent advances in N-heterocyclic carbene catalyzed achiral synthesis
Review Article

Recent advances in controlling the internal and external properties of self-assembling cyclic peptide nanotubes and dimers

Tuning the internal and external properties of self-assembling cyclic peptide nanotubes.

Graphical abstract: Recent advances in controlling the internal and external properties of self-assembling cyclic peptide nanotubes and dimers
Review Article

Spatial organization of multi-enzyme biocatalytic cascades

Multi-enzyme cascades provide a wealth of valuable chemicals. Efficiency of reaction schemes can be improved by spatial organization of biocatalysts. This review will highlight various methods of spatial organization of biocatalysts: fusion, immobilization, scaffolding and encapsulation.

Graphical abstract: Spatial organization of multi-enzyme biocatalytic cascades
Review Article

Square sugars: challenges and synthetic strategies

The synthesis of square sugars requires innovative strategies based on efficient stereoselective methodologies, from organocatalysis to metal carbene insertion.

Graphical abstract: Square sugars: challenges and synthetic strategies
Review Article

A decade of DNA-hybrid catalysis: from innovation to comprehension

Since the pioneering work of Roelfes and Feringa in the field of DNA-based asymmetric catalysis, the unique chirality of oligonucleotides has allowed the development of a variety of asymmetric synthetic transformations. This review offers a complete overview of the field.

Graphical abstract: A decade of DNA-hybrid catalysis: from innovation to comprehension
Review Article

Synergy between experimental and computational studies of aromatic stacking interactions

This review highlights the synergetic exchange of ideas and results between experimental and theoretical chemists en route to the better understanding of aromatic stacking interactions.

Graphical abstract: Synergy between experimental and computational studies of aromatic stacking interactions
Communication

tert-Butyl nitrite (TBN) as the N atom source for the synthesis of substituted cinnolines with 2-vinylanilines and a relevant mechanism was studied

A green method to synthesize cinnolines by 6π electrocyclic reaction with alkenyl amines and TBN has been developed.

Graphical abstract: tert-Butyl nitrite (TBN) as the N atom source for the synthesis of substituted cinnolines with 2-vinylanilines and a relevant mechanism was studied
Communication

Is more better? A comparison of tri- and tetrapeptidic catalysts

From an enzymatic perspective, there is a general notion that the bigger and more complex a catalytically active peptide is the more enzyme-like and the better it should become. But is this really true?

Graphical abstract: Is more better? A comparison of tri- and tetrapeptidic catalysts
Communication

Metal-free synthesis of isatin oximes via radical coupling reactions of oxindoles with t-BuONO in water

A metal-free method for the synthesis of isatin oximes was developed through the radical coupling reactions of oxindoles with t-BuONO.

Graphical abstract: Metal-free synthesis of isatin oximes via radical coupling reactions of oxindoles with t-BuONO in water
Communication

Pd-Catalyzed regioselective sequential meta-, ortho-C–H functionalization of arenes: a predictable approach to the synthesis of polysubstituted β-arylethylamines

Pd-Catalyzed sequential, controllable C–H functionalization of β-arylethylamines at different positions for the construction of polysubstituted arenes is reported.

Graphical abstract: Pd-Catalyzed regioselective sequential meta-, ortho-C–H functionalization of arenes: a predictable approach to the synthesis of polysubstituted β-arylethylamines
Open Access Communication

Imidazolium-labeled glycosides as probes to harness glycosyltransferase activity in human breast milk

Imidazolium-labeled (ITag-) glycosides have been used to harness the glycosyltransferase activity directly from human breast milk (HBM). The technology is exemplified in the synthesis of biologically relevant oligosaccharide analogs, ITag-LacNAc, ITag-Lewisx and ITag-Lewisa, in a matter of days from (HBM) without isolating the enzymes.

Graphical abstract: Imidazolium-labeled glycosides as probes to harness glycosyltransferase activity in human breast milk
Communication

A method for accessing sulfanylfurans from homopropargylic alcohols and sulfonyl hydrazides

A sulfenylation/cyclization reaction has been developed for the synthesis of sulfanylfurans in the presence of iodine.

Graphical abstract: A method for accessing sulfanylfurans from homopropargylic alcohols and sulfonyl hydrazides
Communication

Enantioselective Diels-Alder-lactamization organocascades employing a furan-based diene

α,β-Unsaturated acylammonium salts are useful dienophiles enabling highly enantioselective and stereodivergent Diels-Alder-initiated organocascades with furan-based dienes.

Graphical abstract: Enantioselective Diels-Alder-lactamization organocascades employing a furan-based diene
Communication

Isoafricanol synthase from Streptomyces malaysiensis

A terpene cyclases from Streptomyces malaysiensis was characterised as (+)-isoafricanol synthase and its mechanism was investigated using isotopically labelled substrates.

Graphical abstract: Isoafricanol synthase from Streptomyces malaysiensis
Communication

Lipid-membrane-incorporated arylboronate esters as agents for boron neutron capture therapy

An arylboronate ester bearing a methyl group at both of its ortho positions was stably incorporated into lipid membranes at high concentrations without hydrolysis.

Graphical abstract: Lipid-membrane-incorporated arylboronate esters as agents for boron neutron capture therapy
Communication

Tracking the formation of supramolecular G-quadruplexes via self-assembly enhanced emission

The fluorescence intensity of 8-aryl-2′-deoxyguanosine derivatives enables monitoring the formation of supramolecular G-quadruplexes, opening the door to sensors and probes.

Graphical abstract: Tracking the formation of supramolecular G-quadruplexes via self-assembly enhanced emission
Open Access Communication

Unusual reversal of enantioselectivity in the asymmetric autocatalysis of pyrimidyl alkanol triggered by chiral aromatic alkanols and amines

Temperature dependent inversion of enantioselectivity was observed in the asymmetric autocatalysis reaction when triggered by a wide scope of chiral alcohols and amines.

Graphical abstract: Unusual reversal of enantioselectivity in the asymmetric autocatalysis of pyrimidyl alkanol triggered by chiral aromatic alkanols and amines
Communication

A linear hydroxymethyl tetramate undergoes an acetylation–elimination process for exocyclic methylene formation in the biosynthetic pathway of pyrroindomycins

The exocyclic methylene formation involved in pyrroindomycin biosynthesis is mediated by an enzymatic acetylation–elimination process.

Graphical abstract: A linear hydroxymethyl tetramate undergoes an acetylation–elimination process for exocyclic methylene formation in the biosynthetic pathway of pyrroindomycins
Communication

Fluorometabolite biosynthesis: isotopically labelled glycerol incorporations into the antibiotic nucleocidin in Streptomyces calvus

The pattern of isotope incorporations into the fluorometabolite nucleocidin is explored in Streptomyces calvus from selectively labelled glycerols.

Graphical abstract: Fluorometabolite biosynthesis: isotopically labelled glycerol incorporations into the antibiotic nucleocidin in Streptomyces calvus
Paper

Design, synthesis, and biological activity of second-generation synthetic oleanane triterpenoids

Synthetic manipulation of oleanolic acid affords a novel and biologically active C-24 demethylated CDDO-Me.

Graphical abstract: Design, synthesis, and biological activity of second-generation synthetic oleanane triterpenoids
Open Access Paper

α-Halo carbonyls enable meta selective primary, secondary and tertiary C–H alkylations by ruthenium catalysis

A catalytic meta selective C–H alkylation of arenes is described using a wide range of α-halo carbonyls as coupling partners.

Graphical abstract: α-Halo carbonyls enable meta selective primary, secondary and tertiary C–H alkylations by ruthenium catalysis
Paper

Fluorine-containing bistolanes as light-emitting liquid crystalline molecules

Fluorine-containing dissymmetric bistolanes were found to be promising light-emitting liquid crystals, which could switch luminescence depending on molecular aggregations.

Graphical abstract: Fluorine-containing bistolanes as light-emitting liquid crystalline molecules
Paper

A Pd-catalyzed, boron ester-mediated, reductive cross-coupling of two aryl halides to synthesize tricyclic biaryls

A direct cross-coupling of two different aryl halides in the presence of a palladium catalyst and boron ester was developed to synthesize tricyclic biaryls in one step.

Graphical abstract: A Pd-catalyzed, boron ester-mediated, reductive cross-coupling of two aryl halides to synthesize tricyclic biaryls
Paper

Palladium-catalyzed geometrically selective hydrogenation of (Z)-trifluoromethyl alkenyl triflate: an efficient approach to (Z) or (E)-3,3,3-trifluoropropenyl derivatives

Synthesis of (Z)- or (E)-3,3,3-trifluoropropenyl derivatives with excellent divergent geometric control via hydrogenation of (Z)-trifluoromethyl alkenyl triflates.

Graphical abstract: Palladium-catalyzed geometrically selective hydrogenation of (Z)-trifluoromethyl alkenyl triflate: an efficient approach to (Z) or (E)-3,3,3-trifluoropropenyl derivatives
Paper

Control of the hierarchical assembly of π-conjugated optoelectronic peptides by pH and flow

Coarse-grained molecular simulations reveal the influence of pH and flow on the self-assembly of DFAG-OPV3-GAFD optoelectronic peptides.

Graphical abstract: Control of the hierarchical assembly of π-conjugated optoelectronic peptides by pH and flow
Paper

Biosynthetically-inspired oxidations of capillobenzopyranol

The marine sponge meroterpenoid capillobenzopyranol has been converted into the co-isolated verrubenzospirolactone using simple and selective chemical transformations.

Graphical abstract: Biosynthetically-inspired oxidations of capillobenzopyranol
Paper

Cationic polycyclization of ynamides: building up molecular complexity

Simple activation of readily available ynamides under acidic conditions triggers an unprecedented cationic polycyclization yielding highly substituted polycyclic nitrogen heterocycles.

Graphical abstract: Cationic polycyclization of ynamides: building up molecular complexity
Open Access Paper

Exploring the reversal of enantioselectivity on a zinc-dependent alcohol dehydrogenase

Alcohol Dehydrogenase (ADH) enzymes catalyse the reversible reduction of prochiral ketones to the corresponding alcohols.

Graphical abstract: Exploring the reversal of enantioselectivity on a zinc-dependent alcohol dehydrogenase
Paper

A threonine turnstile defines a dynamic amphiphilic binding motif in the AAA ATPase p97 allosteric binding site

The turnstile motion of two neighboring threonines accommodates both polar and apolar ligands.

Graphical abstract: A threonine turnstile defines a dynamic amphiphilic binding motif in the AAA ATPase p97 allosteric binding site
Paper

Zwitterionic pyrrolidene-phosphonates: inhibitors of the glycoside hydrolase-like phosphorylase Streptomyces coelicolor GlgEI-V279S

We synthesized and evaluated new zwitterionic inhibitors against glycoside hydrolase-like phosphorylase Streptomyces coelicolor (Sco) GlgEI-V279S which plays a role in α-glucan biosynthesis.

Graphical abstract: Zwitterionic pyrrolidene-phosphonates: inhibitors of the glycoside hydrolase-like phosphorylase Streptomyces coelicolor GlgEI-V279S
Paper

A new four-component reaction involving the Michael addition and the Gewald reaction, leading to diverse biologically active 2-aminothiophenes

A Gewald-four component reaction has been successfully developed for the synthesis of a series of compounds containing an indole and a 2-aminothiophene moiety separated by a methylene spacer having anti-proliferative activity.

Graphical abstract: A new four-component reaction involving the Michael addition and the Gewald reaction, leading to diverse biologically active 2-aminothiophenes
Paper

Synthetic glycoconjugates characterize the fine specificity of Brucella A and M monoclonal antibodies

Synthetic oligosaccharide glycoconjugates representing A and M epitopes of Brucella bacteria define the fine specificity of five monoclonal antibodies.

Graphical abstract: Synthetic glycoconjugates characterize the fine specificity of Brucella A and M monoclonal antibodies
Paper

Improving target amino acid selectivity in a permissive aminoacyl tRNA synthetase through counter-selection

We report the selection and characterization of an improved acridon-2-ylalanine aminoacyl tRNA synthetase.

Graphical abstract: Improving target amino acid selectivity in a permissive aminoacyl tRNA synthetase through counter-selection
Paper

Efficient construction of C–N and C–S bonds in 2-iminothiazoles via cascade reaction of enaminones with potassium thiocyanate

Regioselective cascade reactions have been developed by using enaminones and potassium thiocyanate, offering a novel protocol for the synthesis of thiazoles from enaminones.

Graphical abstract: Efficient construction of C–N and C–S bonds in 2-iminothiazoles via cascade reaction of enaminones with potassium thiocyanate
Paper

Synthesis of fused cyanopyrroles and spirocyclopropanes via addition of N-ylides to chalconimines

DABCO-ylides react as a one-carbon source with chalconimines to afford fused cyanopyrroles via [4 + 1] annulation and spirocyclopropanes via [2 + 1] annulation.

Graphical abstract: Synthesis of fused cyanopyrroles and spirocyclopropanes via addition of N-ylides to chalconimines
Paper

Synthesis of non-symmetric viologen-containing ditopic ligands and their Pd(II)/Pt(II)-directed self-assembly

An improved method for the synthesis of non-symmetric viologen-containing ditopic ligands is presented, as well as their Pd(II)/Pt(II)-directed self-assembly into metallacyclic receptors.

Graphical abstract: Synthesis of non-symmetric viologen-containing ditopic ligands and their Pd(ii)/Pt(ii)-directed self-assembly
Paper

In situ formation of pyronin dyes for fluorescence protease sensing

A cutting-edge strategy for fluorogenic sensing of proteases (leucine aminopeptidase for the proof of concept) and based on the “covalent-assembly” principle is reported. Non-fluorescent mixed bis-aryl ethers are readily converted into a fluorescent pyronin through a domino process triggered by the peptide bond cleavage event caused by the targeted enzyme.

Graphical abstract: In situ formation of pyronin dyes for fluorescence protease sensing
Paper

Eight at one stroke – a synthetic tetra-disulfide peptide epitope

A tetra-disulfide peptide dimer, representing an antiparallel hinge, is synthesised without the need for orthogonal cysteine protecting groups.

Graphical abstract: Eight at one stroke – a synthetic tetra-disulfide peptide epitope
Paper

Whole cell-SELEX of aptamers with a tyrosine-like side chain against live bacteria

A dUTP analog modified with a phenol that mimicks tyrosine was used in the selection of DNA aptamers against live bacteria, thereby expanding the binding and recognition capabilities of aptamers.

Graphical abstract: Whole cell-SELEX of aptamers with a tyrosine-like side chain against live bacteria
Paper

Viability of dodecahedrane-forming radical polycyclizations

The results of density functional theory calculations on thiyl radical-promoted polycyclization to form dodecahedrane are described.

Graphical abstract: Viability of dodecahedrane-forming radical polycyclizations
Paper

Enediyne-based protein capture agents: demonstration of an enediyne moiety acting as a photoaffinity label

Two enediyne based protein-capture compounds 1 and 2 were synthesized.

Graphical abstract: Enediyne-based protein capture agents: demonstration of an enediyne moiety acting as a photoaffinity label
Paper

Constrained evolution of a bispecific enzyme: lessons for biocatalyst design

Analysis of the natural evolution of bispecificity in triazine hydrolase highlights the importance of epistasis in protein engineering and evolution.

Graphical abstract: Constrained evolution of a bispecific enzyme: lessons for biocatalyst design
Paper

Push–pull pyropheophorbides for nonlinear optical imaging

We have synthesized derivatives of pyropheophorbide-a with electron donor and acceptor groups which localize in lipid membranes and can be used for multi-photon imaging via second harmonic generation and two-photon excited fluorescence.

Graphical abstract: Push–pull pyropheophorbides for nonlinear optical imaging
Paper

Systematic synthetic and biophysical development of mixed sequence DNA binding agents

Development of heterocyclic diamidines as programmable molecules for sequence-specific DNA recognition.

Graphical abstract: Systematic synthetic and biophysical development of mixed sequence DNA binding agents
Paper

An efficient approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones through a stereoselective tandem Barbier process: divergent syntheses of (3R,4S)-statines, (+)-preussin and (−)-hapalosin

Natural products of (+)-preussin and (−)-hapalosin have been asymmetrically synthesized through the stereoselective tandem Barbier process.

Graphical abstract: An efficient approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones through a stereoselective tandem Barbier process: divergent syntheses of (3R,4S)-statines, (+)-preussin and (−)-hapalosin
Paper

Shining new light on ancient drugs: preparation and subcellular localisation of novel fluorescent analogues of Cinchona alkaloids in intraerythrocytic Plasmodium falciparum

Preparation of fluorescent analogues of quinine and quinidine reveals their localisation in live malaria parasites using confocal and super-resolution microscopy.

Graphical abstract: Shining new light on ancient drugs: preparation and subcellular localisation of novel fluorescent analogues of Cinchona alkaloids in intraerythrocytic Plasmodium falciparum
Paper

OFox imidates as versatile glycosyl donors for chemical glycosylation

OFox imidates are versatile glycosyl donors that can be activated under catalytic conditions and provide excellent stereoselectivities and yields.

Graphical abstract: OFox imidates as versatile glycosyl donors for chemical glycosylation
Paper

The 5-chlorouracil:7-deazaadenine base pair as an alternative to the dT:dA base pair

The 5-Cl-dU:7-deaza-dA base pair can be a substitute for the dT:dA base pair in an enzymatic replication process of 2 kb DNA.

Graphical abstract: The 5-chlorouracil:7-deazaadenine base pair as an alternative to the dT:dA base pair
Paper

β-Amyrin synthase from Euphorbia tirucalli L. functional analyses of the highly conserved aromatic residues Phe413, Tyr259 and Trp257 disclose the importance of the appropriate steric bulk, and cation–π and CH–π interactions for the efficient catalytic action of the polyolefin cyclization cascade

Investigation of functions of aromatic amino acids: steric bulk, cation–π and CH–π interactions.

Graphical abstract: β-Amyrin synthase from Euphorbia tirucalli L. functional analyses of the highly conserved aromatic residues Phe413, Tyr259 and Trp257 disclose the importance of the appropriate steric bulk, and cation–π and CH–π interactions for the efficient catalytic action of the polyolefin cyclization cascade
Paper

Boronic esters as protective groups in carbohydrate chemistry: processes for acylation, silylation and alkylation of glycoside-derived boronates

Boronic esters are employed in streamlined protocols for protection, functionalization and deprotection of glycosides, avoiding isolation and purification of intermediates.

Graphical abstract: Boronic esters as protective groups in carbohydrate chemistry: processes for acylation, silylation and alkylation of glycoside-derived boronates
Paper

Second-generation total synthesis of aplyronine A featuring Ni/Cr-mediated coupling reactions

Second-generation total synthesis of aplyronine A, a potent antitumor marine macrolide, was achieved using Ni/Cr-mediated coupling reactions as key steps.

Graphical abstract: Second-generation total synthesis of aplyronine A featuring Ni/Cr-mediated coupling reactions
Paper

Large-scale synthesis and structural analysis of a synthetic glycopeptide dendrimer as an anti-cancer vaccine candidate

A complex glycopeptide was obtained in multigram as a fully synthetic anti-cancer vaccine for human use.

Graphical abstract: Large-scale synthesis and structural analysis of a synthetic glycopeptide dendrimer as an anti-cancer vaccine candidate
54 articles

About this collection

This on-going collection features all the articles published in Organic and Biomolecular Chemistry in 2017 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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