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.
The Curious Yellow Colouring Matter of the Iceland Poppy
Chemical methods for modification of proteins
The field of protein bioconjugation draws attention from stakeholders in chemistry, biology, and medicine. This review provides an overview of the present status, challenges, and opportunities for organic chemists.
TLR2 agonists and their structure–activity relationships
We review the structure–activity relationships and synthetic studies of TLR2 agonists – important chemical targets in immunotherapy.
Recent development in the synthesis of C-glycosides involving glycosyl radicals
C-Glycosylation involving glycosyl radical intermediates is a particularly effective approach to access C-glycosides, which are core units of a great number of natural products, bioactive compounds and marketed drugs.
Enzymatic glycosylation involving fluorinated carbohydrates
This contribution reviews the enzymatic synthesis, including optimisation efforts, of fluorinated carbohydrates involving fluorinated donors and/or acceptors, as well as the enzymatic activation of the fluorinated donors.
Multiphosphorylated peptides: importance, synthetic strategies, and applications for studying biological mechanisms
Advances in the synthesis of multiphosphorylated peptides and peptide libraries: tools for studying the effects of phosphorylation patterns on protein function and regulation.
Recent advances in β-L-rhamnosylation
This review describes various methodologies for the stereoselective 1,2-cis glycosylation of L-rhamnose leading to β-L-rhamnosides and their applications in oligosaccharide synthesis.
Synthesis of trehalose glycolipids
Chemical synthesis of trehalose glycolipids such as DAT, TDM, SL-1, SL-3, and Ac2SGL from MTb, emmyguyacins from fungi, succinoyl trehalose from rhodococcus, and maradolipids from worms, as well as mycobacterial oligosaccharides is reviewed.
Structure elucidation of bacterial nonribosomal lipopeptides
We provide a summary of the tools, which allow elucidate the structures of nonribosomal lipopetides.
Insights into DNA catalysis from structural and functional studies of the 8-17 DNAzyme
The review examines functional knowledge gathered over two decades of research on the 8-17 DNAzyme, focusing on three aspects: the structural requirements for catalysis, the role of metal ions and the participation of general acid-base catalysis.
Staphylococcus aureus capsular polysaccharides: a structural and synthetic perspective
This review surveys known structures of staphylococcal polysaccharides and summarizes all synthetic efforts to obtain these sequences.
Mechanistic and structural studies into the biosynthesis of the bacterial sugar pseudaminic acid (Pse5Ac7Ac)
The nonulosonic acid sugar pseudaminic acid, Pse5Ac7Ac, is present on the surface of a number of human pathogens, herein we review the mechanistic and structural characterisation of the enzymes responsible for its biosynthesis in bacteria.
G-quadruplexes as versatile scaffolds for catalysis
This review summarizes the beginning, progress, and prospects of non-canonical DNA-based hybrid catalysts focusing on G-quadruplexes as versatile scaffolds for catalysis.
Stabilization of the triple helix in collagen mimicking peptides
The review classifies existing chemical approaches towards stronger triple helical assemblies in peptides.
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.
Synthetic strategies for fluorination of carbohydrates
Different synthetic strategies for accomplishing regio- and stereoselective fluorinations of carbohydrate scaffolds are discussed in light of the biological implications arising from such substitutions.
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.
Versatility of glycals in synthetic organic chemistry: coupling reactions, diversity oriented synthesis and natural product synthesis
Versatility of glycals in the stereoselective synthesis of natural products.
Saturated bioisosteres of benzene: where to go next?
Saturated bioisosteres for ortho- and meta-substituted benzenes remain a current challenge for chemists.
The expanding spectrum of diketopiperazine natural product biosynthetic pathways containing cyclodipeptide synthases
Tailoring enzymes decorate diketopiperazines to yield unique structures and biological functions.
Emerging applications of peptide–oligonucleotide conjugates: bioactive scaffolds, self-assembling systems, and hybrid nanomaterials
Peptide–oligonucleotide conjugates (POCs) are covalent constructs that link a molecule like DNA to a synthetic peptide sequences.
Rearranged ergostane-type natural products: chemistry, biology, and medicinal aspects
Rearranged ergostane-type natural products are structurally intriguing and exhibit biologically relevant properties.
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.
Fluorogenic probes for super-resolution microscopy
Fluorogenic probes efficiently reduce non-specific background signals, which often results in highly improved signal-to-noise ratios.
Azobenzene-based small molecular photoswitches for protein modulation
This review highlights the design strategies of azobenzene photoswitches as well as their applications in the manipulation of biological systems.
Lasso peptides: chemical approaches and structural elucidation
The diverse functionality and the extraordinary stability of lasso peptides make these molecules attractive scaffolds for drug discovery. The ability to generate lasso peptides chemically remains a challenging endeavor.
Biosynthesis of the teleocidin-type terpenoid indole alkaloids
Teleocidin B is a terpenoid indole alkaloid with unique structures including indolactam and cyclic terpenoid, and is a strong protein kinase C activator. In this review, we describe the isolation and biosynthetic studies of teleocidins.
The synthesis of mono-alkyl phosphates and their derivatives: an overview of their nature, preparation and use, including synthesis under plausible prebiotic conditions
Nucleic acids, phospholipids and other organic phosphates play central roles in biological pathways.
C8-Guanine modifications: effect on Z-DNA formation and its role in cancer
Participation of Z DNA in normal and disease related biological processes.
Recent progress of C-glycosylation methods in the total synthesis of natural products and pharmaceuticals
C-Glycosylation has found widespread use in the synthesis of biomedically important natural products and pharmaceuticals.
Target specificity of mammalian DNA methylation and demethylation machinery
We review here the molecular mechanisms employed by DNMTs and TET enzymes that are responsible for shaping the DNA methylation pattern of a mammalian cell.
The renascence of continuous-flow peptide synthesis – an abridged account of solid and solution-based approaches
Within a decade of Merrifield's seminal description of solid-phase peptide synthesis, the synergies between solid-phase approaches and flow synthesis were noted by a number of groups.
Negishi cross-couplings in the synthesis of amino acids
The application of the Negishi cross-coupling reaction in the synthesis of amino acids is reviewed.
25 years and still going strong: 2′-O-(pyren-1-yl)methylribonucleotides – versatile building blocks for applications in molecular biology, diagnostics and materials science
This review highlights the synthesis, biophysical properties, and wide range of applications of oligonucleotides modified with 2′-O-(pyren-1-yl)methyl-RNA monomers reported over the past 25 years.
Efficient and selective antibody modification with functionalised divinyltriazines
We have developed a highly efficient disulfide rebridging strategy for the modification of antibodies with substituted divinyltriazine linkers.
A [Pd2L4]4+ cage complex for n-octyl-β-D-glycoside recognition
A Pd2L4 coordination cage with improved solubility properties was prepared and used to bind n-octyl glycosides, showing a preference for the all equatorial n-octyl glucoside.
Comparison of disaccharide donors for heparan sulfate synthesis: uronic acids vs. their pyranose equivalents
Disaccharide glycosyl donors were synthesised and directly compared in glycosylations to assess their potential for heparan sulfate oligosaccharide synthesis.
Disulphide-mediated site-directed modification of proteins
Site-directed addition of a single thiols handle to proteins by means of temporary disulphide rebridging of solvent exposed disulphides is obtained with a new labelling reagent.
Genetic dereplication driven discovery of a tricinoloniol acid biosynthetic pathway in Trichoderma hypoxylon
Aldol sensor-inspired fluorescent probes for measuring protein citrullination
Inspired by aldol sensors, a novel series of fluorescent probes were developed for measuring and capturing protein citrullination.
Isocoumarin formation by heterologous gene expression and modification by host enzymes
The polyketide synthase product was converted to its methylated and hydroxylated derivatives by host endogenous enzymes.
Sesquiterpene synthases for bungoene, pentalenene and epi-isozizaene from Streptomyces bungoensis
A sesquiterpene synthase from Streptomyces bungoensis was characterised and produces the new compound bungoene.
Synthesis of paenipeptin C′ analogues employing solution-phase CLipPA chemistry
Thiol–ene CLipPA reaction of a vinyl ester and thiolated peptide for generation of an S-lipidated paenipeptin C′ analogue with broad spectrum antibacterial activity.
Differential scanning fluorimetry (DSF) screen to identify inhibitors of Hsp60 protein–protein interactions
Homo-oligomers are difficult drug targets. Here, Differential Scanning Fluorimetry (DSF) is introduced as a method to identify inhibitors of these systems, by discriminating between oligomers and monomers based on their thermal stability.
Modular control of L-tryptophan isotopic substitution via an efficient biosynthetic cascade
Facile biocatalytic synthesis of isotopically substituted tryptophans.
Synthesis of aryl ethers of carbohydrates via reaction with arynes: selective O-arylation of trans-vicinal dihydroxyl groups in carbohydrates
A new method for the O-arylation of carbohydrates under transition metal-free conditions using arynes as an aryl source has been developed.
Rapid sodium periodate cleavage of an unnatural amino acid enables unmasking of a highly reactive α-oxo aldehyde for protein bioconjugation
A genetically incorporated ThrK unnatural amino acid can undergo rapid periodate oxidation to reveal a reactive internal α-oxo aldehyde.
Conjugating pyrene onto PNA-based fluorescent probes for improved detection selectivity toward double-stranded siRNA
PNA-based fluorescent probes conjugated with the pyrene unit exhibited the improved detection selectivity for double-stranded siRNA.
NBD-based fluorescent probes for separate detection of cysteine and biothiols via different reactivities
A NBD-based fluorescent probe is developed to seperately detect Cys and all biothiols via different reactivity.
A minor structure modification serendipitously leads to a highly carbapenemase-specific fluorogenic probe
A carbapenem-based fluorogenic reagent has been developed to detect the activity of carbapenemases, exhibiting high specificity to all carbapenemases, including both metallo carbapenemases and serine carbapenemases, over other β-lactamases.
A laccase-catalysed tyrosine click reaction
The tyrosine click reaction of peptides/proteins with the tyrosine modification reagent, N-methyl luminol, was catalysed by a laccase in the presence of molecular oxygen (O2) at 37 °C.
Heterologous expression of the trichostatin gene cluster and functional characterization of N-methyltransferase TsnB8
N-Methyltransferase TsnB8 was demonstrated to catalyze successive methyltransfer reactions in the biosynthesis of trichostatin.
The key entity of a DCAR agonist, phosphatidylinositol mannoside Ac1PIM1: its synthesis and immunomodulatory function
We achieved the first synthesis of phosphatidylinositol mannoside Ac1PIM1, and a very potent agonist of an innate immune receptor DCAR is demonstrated.
Introducing sequential aza-amino acids units induces repeated β-turns and helical conformations in peptides
A major current issue in medicinal chemistry is the design of small peptide analogues resistant to proteolysis and able to adopt preferential conformations, while preserving the selectivity and efficiency of natural peptides.
Direct recognition and sensitive detection of circular RNA with ligation-based PCR
A sensitive and specific method for circRNA detection is developed through the direct ligation of two ingeniously designed DNA probes.
Protein labeling approach to improve lysosomal targeting and efficacy of antibody–drug conjugates
An anti-EGFR nanobody was labeled at the C-terminus with a lysosome-sorting NPGY (Asn-Pro-Gly-Tyr) motif via sortase-mediated ligation to enhance the clathrin-mediated endocytosis.
Pseudo-enantiomeric carbohydrate-based N-heterocyclic carbenes as promising chiral ligands for enantiotopic discrimination
The practical synthesis of pseudo-enantiomeric carbohydrate-based NHC–Rh complexes bearing C1 or C3 sterically differentiated positions is reported. We show that steric bulk at either C1 or C3 leads to enantiotopic discrimination in the hydrosilylation of acetophenone.
Peptide precursors that acquire denatured collagen-hybridizing ability by O-to-N acyl migration at physiological pH
Collagen-like peptides containing Gly-Ser O-acyl isopeptide units without self-assembling propensity serve as precursors for collagen-detecting agents.
Synthetic-biology-based discovery of a fungal macrolide from Macrophomina phaseolina
Genome mining and heterologous biosynthesis led to the discovery of a 12 membered macrolide from Macrophomina phaseolina.
Spontaneous oxidative cyclisations of 1,3-dihydroxy-4-dimethylallylnaphthalene to tricyclic derivatives
Radical-involved spontaneous oxidative cyclisations of 1,3-dihydroxy-4-dimethylallylnaphthalene are reported.
Metal-free synthesis of imino-disaccharides and calix-iminosugars by photoinduced radical thiol–ene coupling (TEC)
Deprotected iminosugar alkenes were subjected to thiol–ene coupling with deprotected sugar thiols to afford new imino-disaccharides. Two thiol–ene couplings converted these alkenes into iminosugar thiols and then multivalent iminosugars.
18F-Labeled dihydromethidine: positron emission tomography radiotracer for imaging of reactive oxygen species in intact brain
Dihydromethidine (DHM) labeled with 18F at the para position of the benzene ring has been developed as a positron emission tomography (PET) radiotracer for non-invasive imaging of reactive oxygen species (ROS).
Photosensitised biphotonic chemistry of pyrimidine derivatives
Biphotonic chemistry of pyrimidines is produced using a 355 nm laser and 2-methoxyacetophenone as photosensitiser.
Characterization of the promiscuous N-acyl CoA transferase, LgoC, in legonoxamine biosynthesis
More than 500 siderophores are known to date, but only three were identified to be aryl-containing hydroxamate siderophores, legonoxamines A and B from Streptomyces sp. MA37, and aryl ferrioxamine 2 from Micrococcus luteus KLE1011.
Functionalised thermally induced phase separation (TIPS) microparticles enabled for “click” chemistry
In this study we describe a novel platform for generating functionalised TIPS microparticles for “click” conjugation to various active compounds.
Secondary modification of oxidatively-modified proline N-termini for the construction of complex bioconjugates
A sequential oxidative coupling and oxime or hydrazone ligation method allows construction of bifunctional N-terminal bioconjugates.
Automated access to well-defined ionic oligosaccharides
Automated Glycan Assembly grants access to ionic oligosaccharides for structural studies.
The effect of spermidine on guanine decomposition via photoinduced electron transfer in DNA
The addition of spermidine caused the attenuation of guanine decomposition via photoinduced electron transfer in pyrene-modified DNA, and higher added concentrations of spermidine resulted in the promotion of decomposition in condensed DNA.
About this collection
The latest articles published in Organic and Biomolecular Chemistry related to chemical biology research.