Aromatic-fused diketophosphanyl-core organic functional materials: phosphorus mimics of imides or beyond?
The recent advancement in aromatic-fused diketophosphanyl compounds (phosphorus-analogues of aromatic imides) as organic functional materials is reviewed.
Hantzsch esters: an emerging versatile class of reagents in photoredox catalyzed organic synthesis
This minireview highlights the recent advances in the chemistry of Hantzsch esters in photoredox catalyzed organic synthesis, with particular emphasis placed on reaction mechanisms.
Supramolecular assembly of functional peptide–polymer conjugates
The following review gives an overview about synthetic peptide–polymer conjugates as macromolecular building blocks and their self-assembly into a variety of supramolecular architectures, from supramolecular polymer chains, to anisotropic 1D arrays, 2D layers, and more complex 3D networks.
Full solid-phase total synthesis of macrocyclic natural peptides using four-dimensionally orthogonal protective groups
This review focuses on four-dimensionally orthogonal protective group strategies for the full solid-phase synthesis of macrocyclic natural peptides.
Organoboron synthesis via ring opening coupling reactions
This review covers new trends towards the selective synthesis of organoboron compounds where boron reagents and cyclic substrates participate in the generation of carbanions, in the presence of stoichiometric amounts of main-group metals or catalytic amounts of transition metal complexes, via ring opening coupling transformations.
Chemical ADP-ribosylation: mono-ADPr-peptides and oligo-ADP-ribose
A review of recent advances towards synthetic ADP-ribosylated proteins and oligo-ADP-ribose chains.
Synthesis of carbohydrate building blocks via regioselective uniform protection/deprotection strategies
Scope 1: sugar is uniformly protected leaving only one (or two) free hydroxyl group; scope 2: uniformly protected sugar is deprotected to liberate only one (or two) hydroxyl group.
Chemical composition of DNA-encoded libraries, past present and future
We discuss here the chemical composition of DNA-encoded libraries likely to be made in the near future.
Photoimmunoconjugates: novel synthetic strategies to target and treat cancer by photodynamic therapy
The most recent advances in targeted PDT are revised, presenting novel photoimmunoconjugates and their biological results.
The expanding spectrum of diketopiperazine natural product biosynthetic pathways containing cyclodipeptide synthases
Tailoring enzymes decorate diketopiperazines to yield unique structures and biological functions.
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.
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 transition metal-catalyzed C(sp2)–H nitration
This review updates advances of direct C(sp2)–H nitration for the synthesis of nitroaromatic compounds and the mechanisms during the past decade.
SuperQuat chiral auxiliaries: design, synthesis, and utility
The design, synthesis and outline of some of the most common synthetic applications of the SuperQuat (4-substituted 5,5-dimethyloxazolidine-2-one) family of chiral auxiliaries, developed to address the shortcomings of the Evans (4-substituted oxazolidin-2-one) family of chiral auxiliaries, are presented.
One-pot multi-segment condensation strategies for chemical protein synthesis
This paper describes recent advances of one-pot multi-segment condensation strategies based on kinetically controlled strategies and/or protecting group-removal strategies in chemical protein synthesis.
Recent developments in photochemical reactions of diazo compounds
Chemistry of diazo compounds is dominated by transition metal catalysis but recently, photoinitiated reactions of diazo compounds have attracted a lot of attention. This mini-review describes recent discoveries on the reactivity of diazo compounds under light irradiation.
Fluorogenic probes for super-resolution microscopy
Fluorogenic probes efficiently reduce non-specific background signals, which often results in highly improved signal-to-noise ratios.
Non-toxic cyanide sources and cyanating agents
This review focuses on alternative cyanide sources and cyanating agents which are less hazardous than HCN or its salts.
Pyridine-catalyzed desulfonative borylation of benzyl sulfones
Herein, we report the transition-metal free, pyridine-catalyzed desulfonative borylation of benzyl sulfones with bis(pinacolato)diboron (B2pin2).
Palladium-catalyzed intermolecular allenylation reactions of 2,3-disubstituted indoles and allenyl carbonate
A palladium-catalyzed C3-allenylation of non-strained 2,3-disubstituted indoles with allenyl carbonate has been developed.
Hydantoin analogs inhibit the fully assembled ClpXP protease without affecting the individual peptidase and chaperone domains
A new class of non-covalent inhibitors attenuates ClpXP turnover, neither impairing chaperone nor peptidase activity.
A chemical approach for the synthesis of the DNA-binding domain of the oncoprotein MYC
We describe the first chemical synthesis of a functional mutant of the DNA binding domain of the oncoprotein MYC, using two alternative strategies which involve either one or two Native Chemical Ligations (NCLs).
Experimental and numerical evaluation of a genetically engineered M13 bacteriophage with high sensitivity and selectivity for 2,4,6-trinitrotoluene
This study includes the experimental results of a sensitive M13 bacteriophage-based sensor system that are well matched with the quantum mechanics calculation.
Planarized B,N-phenylated dibenzoazaborine with a carbazole substructure: electronic impact of the structural constraint
Structural constraint in B,N-phenylated dibenzoazaborine alters the π-conjugation mode and furnishes intense deep-blue emission and intriguing electrochemical properties.
β-Glucuronidase triggers extracellular MMAE release from an integrin-targeted conjugate
A non-internalizing conjugate targeting αvβ3 integrin inhibits the proliferation of integrin-expressing cancer cells in the presence of β-glucuronidase.
Achiral amino acid glycine acts as an origin of homochirality in asymmetric autocatalysis
Achiral glycine acts as the origin of chirality in conjunction with asymmetric autocatalysis to afford highly enantioenriched compound.
The asymmetric construction of CF3-containing spiro-thiazolone-pyrrolidine compounds via [3 + 2] cycloaddition
An organocatalytic method for the asymmetric construction of CF3-containing spiro-thiazolone-pyrrolidine compounds has been developed.
A parallel permeability assay of peptides across artificial membranes and cell monolayers using a fluorogenic reaction
An alkyne tag and a fluorogenic reaction enabled the rapid parallel evaluation of membrane permeability of peptides across artificial membranes and cell monolayers.
Naphthalimide-containing conjugated polyelectrolytes with different chain configurations
Different polymer chain configurations along the main chains of poly(naphthalimide and phenylene ethynylene)s lead to dramatic differences in polymer conformations and photophysical properties.
Catalytic asymmetric aza-Michael addition of fumaric monoacids with multifunctional thiourea/boronic acids
Chiral multifunctional thiourea/boronic acid catalysts enabled the synthesis of N-hydroxyaspartate derivatives applicable for KAHA amidation through acid-β selective aza-Michael addition.
Oxidative C(sp3)–H functionalization of methyl-azaheteroarenes: a facile route to 1,2,4-triazolo[4,3-a]pyridines
An oxidative [4 + 1] annulation for triazolo[4,3-a]pyridine–quinoline linked diheterocycle synthesis via functionalization of the sp3 C–H bonds of 2-methyl-azaheteroarenes has been developed.
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.
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.
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.
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.
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.
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.
Synthesis and biological evaluation of fluorinated analogues of ripostatin A
A last stage click-chemistry approach to synthesize the heterocycle-containing derivatives of fluorinated ripostatin A was developed.
Biosynthesis of the uridine-derived nucleoside antibiotic A-94964: identification and characterization of the biosynthetic gene cluster provide insight into the biosynthetic pathway
The biosynthetic pathway of the uridine-derived nucleoside antibiotic A-94964 was proposed via in silico analysis coupled with gene deletion experiments.
Biosynthesis of lagopodins in mushroom involves a complex network of oxidation reactions
Targeted gene knockout in Coprinopsis cinerea, yeast in vivo bioconversion and in vitro assays elucidated the lagopodin biosynthetic pathway, including a complexity-generating network of oxidation steps.
Synthesis and electrochromic behavior of a multi-electron redox-active N-heteroheptacenequinone
N-Heteropentacenequinone can accept four electrons as well as show electrochromism.
BPO-promoted direct oxidative C–H functionalization of unactivated alkanes into 6-alkyl-6H-benzo[c]chromenes under transition-metal-free conditions
A simple and efficient BPO-promoted free radical-based cascade reaction of biaryl vinyl ethers with easily available unactivated alkanes has been developed.
Mild C–H functionalization of alkanes catalyzed by bioinspired copper(II) cores
Three new copper(II) coordination compounds with aminoalcohol and carboxylate type ligands were self-assembled, fully characterized, and applied as efficient homogeneous catalysts for the mild oxidation and carboxylation of saturated hydrocarbons.
Membrane-specific spin trap, 5-dodecylcarbamoyl-5-N-dodecylacetamide-1-pyroline-N-oxide (diC12PO): theoretical, bioorthogonal fluorescence imaging and EPR studies
Lipophilic spin trap, diC12PO, forms radical- and cyclo-adduct with implication as membrane antioxidant and for nitrone cellular visualization using bioorthogonal imaging approach, respectively.
An enzymatic Finkelstein reaction: fluorinase catalyses direct halogen exchange
The fluorinase enzyme catalyses a direct displacement of bromide and iodide by fluoride ion from 5′-bromodeoxyadenosine and 5′-iododeoxyadenosine respectively to form 5′-fluorodeoxyadenosine in the absence of L-methionine or S-adenosyl-L-methionine.
Ruthenium(II)-catalysed selective C(sp2)–H bond benzoxylation of biologically appealing N-arylisoindolinones
A general site- and regio-selective aromatic C–H bond benzoxylation reaction using biologically-relevant isoindolinones as weak directing groups has been developed.
The role of Brønsted base basicity in estimating carbon acidity at enzyme active sites: a caveat
Using the pKE-BH+a value of the Brønsted base catalyst in the enzyme–substrate complex can overestimate the extent to which an enzyme lowers the substrate's pKC–Ha value.
Exploring the strength of a hydrogen bond as a function of steric environment using 1,2-azaborine ligands and engineered T4 lysozyme receptors
The relationship between the steric demand of the ligand and hydrogen bonding strength in the context of ligand–protein binding is revealed using engineered T4 lysozymes as the model biomacromolecules and 1,2-azaborines as ligands.
The cubane paradigm in bioactive molecule discovery: further scope, limitations and the cyclooctatetraene complement
Trials and tribulations of the cubane paradigm in biomolecule discovery highlight synthetic limitations, culminating in a continuing guide for practitioners, which includes cyclooctatetraene.
Improvement of the versatility of an arabinofuranosidase against galactofuranose for the synthesis of galactofuranoconjugates
A new performant biocatalyst was developed for the synthesis of O-, S- and acyl-galactofuranoconjugates.
Structures and biological activities of cycloheptamycins A and B
The structures, absolute configurations and biological activities, particularly against P. acnes, of the cycloheptamycin family of cycloheptadepsipeptides are presented.
Copper-catalysed borylation of aryl chlorides
The first example of a Cu-catalysed borylation of a wide range of aryl chlorides with different electronic and steric properties is mediated by a readily prepared NHC-stabilised Cu catalyst and KOtBu. The aryl chlorides are converted into their corresponding arylboronic esters using B2pin2 or B2neop2 as the boron reagent.
Tumour-targeting photosensitisers for one- and two-photon activated photodynamic therapy
Efficient receptor-mediated delivery of a folate-targeted photosensitiser to kill cancer cells following two-photon excitation in the near-infrared is demonstrated.
Identification of crucial bottlenecks in engineered polyketide biosynthesis
Quo vadis combinatorial biosynthesis: STOP signs through substrate scope limitations lower the yields in engineered polyketide biosynthesis using cis-AT polyketide synthases.
Synthesis of fluorenyl alcohols via cooperative palladium/norbornene catalysis
Catalytic synthesis of fluorenols by synchronization of two stoichiometric reactions: (a) Pd(II)-mediated oxidation of alcohols to ketones and (b) Pd(0)/norbornene-catalyzed reaction of aryl iodides with ortho-bromoacetophenones.
Bis-aminocyclopropenylidene carbene borane catalyzed imine hydrogenation
Borenium-catalyzed hydrogenations of an imine made from a benzylamine are enabled by a steric interplay between cyclohexylborane and a BAC carbene: both are necessary for efficient reactivity.
Direct Csp3–H methylenation of 2-arylacetamides using DMF/Me2NH-BH3 as the methylene source
A direct Csp3–H methylenation reaction using DMF/Me2NH-BH3 as the methylene source was developed for the synthesis of useful 2-arylarylacrylamides.
Design of thiazole orange oligonucleotide probes for detection of DNA and RNA by fluorescence and duplex melting
We report fluorogenic duplex-stabilising thiazole orange (TO) functionalised oligonucleotides for nucleic acid detection in which TO is attached to the nucleobase or sugar of thymidine.
Pseudoenantiomeric glycoclusters: synthesis and testing of heterobivalency in carbohydrate–protein interactions
Multivalent carbohydrate–protein interactions are key events in cell recognition processes and have been extensively studied by means of synthetic glycomimetics.
Triazole functionalized acyclic cucurbit[n]uril-type receptors: host·guest recognition properties
The synthesis, characterization, and molecular recognition properties of 2–4 toward organic ammonium ions in water is reported.
Fusaresters A–E, new γ-pyrone-containing polyketides from fungus Fusarium sp. Hungcl and structure revision of fusariumin D
Chemical investigation of a marine-derived fungus Fusarium sp. Hungcl afforded five new γ-pyrone-containing polyketides, fusaresters A–E.
Synthesis and biophysical properties of carbamate-locked nucleic acid (LNA) oligonucleotides with potential antisense applications
Carbamate-LNA oligonucleotides have improved biophysical properties for theraputic applications.
Selective synthesis of 3-deoxy-5-hydroxy-1-amino-carbasugars as potential α-glucosidase inhibitors
A selective synthesis of 13 and 15, which could be converted to carbasugars as α-glucosidase inhibitors, was developed.
SO2F2 mediated transformation of pyrazolones into pyrazolyl fluorosulfates
The construction of a class of novel N-heterocyclic molecules containing both pyrazole and fluorosulfate functionalities was achieved through the reactions of pyrazolones with SO2F2 in good to excellent yields.
Diversity of mechanisms in Ras–GAP catalysis of guanosine triphosphate hydrolysis revealed by molecular modeling
Different mechanisms of GTP hydrolysis by Ras–GAP are revealed in QM/MM simulations depending on molecular groups at position 61 in Ras.
Silver-mediated three-component cycloaddition reaction for direct synthesis of 1-N-vinyl-substituted 1,2,3-triazoles
Direct synthesis of 1-N-vinyl-1,2,3-triazoles via silver-mediated three-component cycloaddition reaction of phenylacetylenes, trimethylsilylazide, and 1,3-dicarbonyl compounds is presented.
Evaluating aryl esters as bench-stable C(1)-ammonium enolate precursors in catalytic, enantioselective Michael addition–lactonisations
An evaluation of a range of aryl, alkyl and vinyl esters as prospective C(1)-ammonium enolate precursors in enantioselective Michael addition–lactonisation processes with (E)-trifluoromethylenones using isothiourea catalysis is reported.
One-pot ortho-amination of aryl C–H bonds using consecutive iron and copper catalysis
A one-pot ortho-amination of activated arenes using sequential iron and copper catalysis has been developed and utilised for the late-stage structural diversification of biologically active 3,4-dihydroquinolin-2-ones.
Demystifying a hexuronic acid ligand that recognizes Toxoplasma gondii and blocks its invasion into host cells
Toxoplasma gondii is a ubiquitous eukaryotic pathogen responsible for toxoplasmosis in humans and animals.
About this collection
This on-going collection features all the articles published in Organic & Biomolecular Chemistry in 2019 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!