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Themed collection Organic & Biomolecular Chemistry HOT article collection

44 items
Communication

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.

Graphical abstract: The asymmetric construction of CF3-containing spiro-thiazolone-pyrrolidine compounds via [3 + 2] cycloaddition
From the themed collection: Synthetic methodology in OBC
Communication

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.

Graphical abstract: Photoinduced decarboxylative azidation of cyclic amino acids
From the themed collection: Synthetic methodology in OBC
Communication

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.

Graphical abstract: Synthesis of fluoroalkylated alkynes via visible-light photocatalysis
From the themed collection: Synthetic methodology in OBC
Communication

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.

Graphical abstract: Synthesis and biological evaluation of fluorinated analogues of ripostatin A
Paper

The versatile use of solubilizing trityl tags for difficult peptide/protein synthesis

Our solubilizing trityl tags designed for difficult peptide/protein synthesis proved applicable to metal-free radical-triggered desulfurization and an Ag-mediated thioester method.

Graphical abstract: The versatile use of solubilizing trityl tags for difficult peptide/protein synthesis
From the themed collection: Synthetic methodology in OBC
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
Communication

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.

Graphical abstract: Synthesis of the β-linked GalNAc-Kdo disaccharide antigen of the capsular polysaccharide of Kingella kingae KK01
Communication

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.

Graphical abstract: An enantioselective synthesis of α-alkylated pyrroles via cooperative isothiourea/palladium catalysis
From the themed collection: Synthetic methodology in OBC
Communication

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.

Graphical abstract: Naphthalimide-containing conjugated polyelectrolytes with different chain configurations
Communication

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.

Graphical abstract: Oxidative C(sp3)–H functionalization of methyl-azaheteroarenes: a facile route to 1,2,4-triazolo[4,3-a]pyridines
From the themed collection: Synthetic methodology in OBC
Paper

On water: iodine-mediated direct construction of 1,3-benzothiazines from ortho-alkynylanilines by regioselective 6-exo-dig cyclization

Herein, we report the 6-exo-dig ring closure of ortho-alkynylanilines with readily available aroyl isothiocyanate.

Graphical abstract: On water: iodine-mediated direct construction of 1,3-benzothiazines from ortho-alkynylanilines by regioselective 6-exo-dig cyclization
From the themed collection: Synthetic methodology in OBC
Review Article

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.

Graphical abstract: Recent developments in photochemical reactions of diazo compounds
From the themed collection: Synthetic methodology in OBC
Paper

Computational and experimental investigation on the BCl3 promoted intramolecular amination of alkenes and alkynes

The BCl3 promoted aminoboration of alkenes and alkynes was investigated both computationally and experimentally, leading to the discovery of a metal-free hydroamination of alkynes.

Graphical abstract: Computational and experimental investigation on the BCl3 promoted intramolecular amination of alkenes and alkynes
Communication

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.

Graphical abstract: A parallel permeability assay of peptides across artificial membranes and cell monolayers using a fluorogenic reaction
Paper

Freezing-assisted synthesis of covalent C–C linked bivalent and bispecific nanobodies

C–N linked bivalent nanobody (upper) and C–C linked nanobody (bottom) presented as cartoon. (The elephant represents the nanobody; the banana represents the antigen).

Graphical abstract: Freezing-assisted synthesis of covalent C–C linked bivalent and bispecific nanobodies
Paper

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.

Graphical abstract: Sulfur polymer composites as controlled-release fertilisers
Open Access Review Article

Fluorogenic probes for super-resolution microscopy

Fluorogenic probes efficiently reduce non-specific background signals, which often results in highly improved signal-to-noise ratios.

Graphical abstract: Fluorogenic probes for super-resolution microscopy
Review Article

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.

Graphical abstract: One-pot multi-segment condensation strategies for chemical protein synthesis
Paper

Cascade cyclization and intramolecular nitrone dipolar cycloaddition and formal synthesis of 19-hydroxyibogamine

Condensation of hydroxylamine and an aldehyde gave an azabicyclo[2.2.2]octane (isoquinuclidine) that was applied to a formal synthesis of 19-hydroxyibogamine.

Graphical abstract: Cascade cyclization and intramolecular nitrone dipolar cycloaddition and formal synthesis of 19-hydroxyibogamine
Paper

Structure elucidation and biosynthetic gene cluster analysis of caniferolides A–D, new bioactive 36-membered macrolides from the marine-derived Streptomyces caniferus CA-271066

The structures of caniferolides A–D have been determined combining NMR and bioinformatics prediction of the absolute configuration.

Graphical abstract: Structure elucidation and biosynthetic gene cluster analysis of caniferolides A–D, new bioactive 36-membered macrolides from the marine-derived Streptomyces caniferus CA-271066
From the themed collection: Chemical biology in OBC
Review Article

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.

Graphical abstract: Photoimmunoconjugates: novel synthetic strategies to target and treat cancer by photodynamic therapy
Paper

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.

Graphical abstract: Enantioselective syntheses and application of 4-epi-galiellalactone and the corresponding activity-based probe: from strained bicycles to strained tricycles
Paper

Identification of the common biosynthetic gene cluster for both antimicrobial streptoaminals and antifungal 5-alkyl-1,2,3,4-tetrahydroquinolines

The new subfamily of type II PKS gene cluster is responsible for biosynthesis of structurally distinct streptoaminals (STAMs) and 5-alkyl-1,2,3,4-tetrahydroquinolines (5aTHQs).

Graphical abstract: Identification of the common biosynthetic gene cluster for both antimicrobial streptoaminals and antifungal 5-alkyl-1,2,3,4-tetrahydroquinolines
Review Article

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.

Graphical abstract: Recent advances in transition metal-catalyzed C(sp2)–H nitration
From the themed collection: Synthetic methodology in OBC
Paper

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.

Graphical abstract: Sialylated variants of lacto-N-tetraose exhibit antimicrobial activity against Group B Streptococcus
Paper

Phosphine-catalyzed [4 + 2] cyclization of para-quinone methide derivatives with allenes

The first [4 + 2] cyclization of para-quinone methide derivatives with allenes has been established via phosphine catalysis, which afforded a series of chroman derivatives in high yields (up to 97%) and excellent (E/Z)-selectivities (all >95 : 5 E/Z).

Graphical abstract: Phosphine-catalyzed [4 + 2] cyclization of para-quinone methide derivatives with allenes
From the themed collection: Synthetic methodology in OBC
Communication

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.

Graphical abstract: Catalytic asymmetric aza-Michael addition of fumaric monoacids with multifunctional thiourea/boronic acids
Paper

Silver(I)-catalyzed addition of pyridine-N-oxides to alkynes: a practical approach for N-alkenoxypyridinium salts

A smooth catalytic approach to N-alkenoxypyridinium salts using pyridine-N-oxides as the nucleophilic partner with alkynes under acidic conditions was developed.

Graphical abstract: Silver(i)-catalyzed addition of pyridine-N-oxides to alkynes: a practical approach for N-alkenoxypyridinium salts
From the themed collection: Synthetic methodology in OBC
Communication

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.

Graphical abstract: Using automated glycan assembly (AGA) for the practical synthesis of heparan sulfate oligosaccharide precursors
Paper

Self-templated synthesis of amide catenanes and formation of a catenane coordination polymer

A metal-free synthesis of [2]catenanes is exploited to prepare an interlocked ligand that self-assembles with Ag(I) to form one-dimensional metallo-polycatenanes.

Graphical abstract: Self-templated synthesis of amide catenanes and formation of a catenane coordination polymer
From the themed collection: Supramolecular chemistry in OBC
Paper

Substrate selectivity and its mechanistic insight of the photo-responsive non-nucleoside triphosphate for myosin and kinesin

Selective photoregulation of myosin over kinesin using azobenzene-tethered triphosphate.

Graphical abstract: Substrate selectivity and its mechanistic insight of the photo-responsive non-nucleoside triphosphate for myosin and kinesin
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
Review Article

Rearranged ergostane-type natural products: chemistry, biology, and medicinal aspects

Rearranged ergostane-type natural products are structurally intriguing and exhibit biologically relevant properties.

Graphical abstract: Rearranged ergostane-type natural products: chemistry, biology, and medicinal aspects
Review Article

The expanding spectrum of diketopiperazine natural product biosynthetic pathways containing cyclodipeptide synthases

Tailoring enzymes decorate diketopiperazines to yield unique structures and biological functions.

Graphical abstract: The expanding spectrum of diketopiperazine natural product biosynthetic pathways containing cyclodipeptide synthases
From the themed collection: Chemical biology in OBC
Paper

Exploiting the vicinal disubstituent effect on the diastereoselective synthesis of γ and δ lactones

Trifluoroacetic acid catalysed lactonization of vicinal disubstituted γ-hydroxyesters was investigated in different solvents.

Graphical abstract: Exploiting the vicinal disubstituent effect on the diastereoselective synthesis of γ and δ lactones
Paper

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.

Graphical abstract: Why do A·T and G·C self-sort? Hückel aromaticity as a driving force for electronic complementarity in base pairing
Communication

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.

Graphical abstract: Biosynthesis of lagopodins in mushroom involves a complex network of oxidation reactions
Open Access Paper

Tetrafluoropyridyl (TFP): a general phenol protecting group readily cleaved under mild conditions

Herein we introduce tetrafluoropyridyl (TFP) as a new general protecting group for phenols. The TFP protecting group is readily cleaved under mild conditions.

Graphical abstract: Tetrafluoropyridyl (TFP): a general phenol protecting group readily cleaved under mild conditions
From the themed collection: Synthetic methodology in OBC
Review Article

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.

Graphical abstract: Non-toxic cyanide sources and cyanating agents
From the themed collection: Synthetic methodology in OBC
Communication

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.

Graphical abstract: Biosynthesis of the uridine-derived nucleoside antibiotic A-94964: identification and characterization of the biosynthetic gene cluster provide insight into the biosynthetic pathway
Review Article

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.

Graphical abstract: Next generation diversity-oriented synthesis: a paradigm shift from chemical diversity to biological diversity
From the themed collection: Synthetic methodology in OBC
Review Article

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.

Graphical abstract: Use of ArSO2SRf reagents: an efficient tool for the introduction of SRf moieties
From the themed collection: Synthetic methodology in OBC
Paper

Luminescent conjugates between dinuclear rhenium complexes and 17α-ethynylestradiol: synthesis, photophysical characterization, and cell imaging

New luminescent conjugates between dinuclear rhenium complexes and an estradiol moiety.

Graphical abstract: Luminescent conjugates between dinuclear rhenium complexes and 17α-ethynylestradiol: synthesis, photophysical characterization, and cell imaging
Review Article

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.

Graphical abstract: SuperQuat chiral auxiliaries: design, synthesis, and utility
From the themed collection: Synthetic methodology in OBC
44 items

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!

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