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.
Recent advances in the synthesis of C-terminally modified peptides
A go-to compilation of recent strategies to access C-terminally modified peptides contextualized by a discussion of the major synthetic challenges that have historically hampered progress in this area.
Development and utilization of peptide-based quorum sensing modulators in Gram-positive bacteria
This review discusses the development of peptide-based quorum sensing modulators and their use as potential therapeutics.
Rational design of small molecule fluorescent probes for biological applications
Guidelines based on photophysical tuning, reactivity, isomerization, and energy transfer for rational design of synthetic fluorescent probes for biological systems.
Structural advances of Siglecs: insight into synthetic glycan ligands for immunomodulation
This review summarizes the natural and synthetic glycan ligands of Siglecs and the growing body of knowledge for structural features governing sialic acid recognition.
The curious yellow colouring matter of the Iceland poppy
This account provides an chronological overview of the fascinating history of the pigment responsible for the yellow colour of the Iceland poppy (Papaver nudicaule).
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.
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.
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.
Modular quadruplex–duplex hybrids as biomolecular scaffolds for asymmetric Michael addition reactions
We report modular QD hybrid DNA catalysts containing bipyridine ligands and hydrogen donor moieties for the asymmetric Michael addition reactions.
DNA-organized artificial LHCs – testing the limits of chromophore segmentation
DNA-organized LHCs show efficient excitation energy transfer along disjointed stacks of light-harvesting chromophores.
A set of rhamnosylation-specific antibodies enables detection of novel protein glycosylations in bacteria
Chemical curiosity or not? Specific antibodies to study the rhamnoproteome in bacteria.
Use of solid-supported 4-fluorophenyl 3-nitro-2-pyridinesulfenate in the construction of disulfide-linked hybrid molecules
A new solid-supported 4-fluorophenyl 3-nitro-2-pyridinesulfenate is useful for the efficient synthesis of a cyclic peptide and a disulfide-linked glycoconjugate.
Chemoselective activation of ethyl vs. phenyl thioglycosides: one-pot synthesis of oligosaccharides
Ethyl thioglycosides could be selectively activated in the presence of phenyl thioglycosides carrying the same or even more armed protecting group pattern.
An enzyme-triggered turn-on fluorescent probe based on carboxylate-induced detachment of a fluorescence quencher
A new class of turn-on fluorescent probes for an enzyme was developed to increase the responsiveness to the enzyme without generating any by-products.
Defluorination of 4-fluorothreonine by threonine deaminase
Threonine deaminase from E. coli catalyses defluorination on 4-fluorothreonine.
Monitoring ligand-mediated helix 12 transitions within the human estrogen receptor α using bipartite tetracysteine display
Fluorescent labeling coupled with bipartite tetracysteine display enables the surveillance of ligand-mediated helix 12 transitions within the estrogen receptor α ligand-binding domain.
On the mechanism of ophiobolin F synthase and the absolute configuration of its product by isotopic labelling experiments
The cyclisation mechanism of ophiobolin F synthase AcldOS and the absolute configuration of its product were investigated by isotopic labelling experiments.
Stereoselective synthesis of allele-specific BET inhibitors
Developing stereoselective synthetic routes that are efficient and cost-effective allows easy access to allele-selective bumped BET inhibitors.
Magnesium-specific ring expansion/contraction catalysed by the class II diterpene cyclase from pleuromutilin biosynthesis
The class II diterpene cyclase from pleuromutilin biosynthesis, selectively with magnesium, catalyzes ring expansion/contraction between its initial mutildienyl diphosphate product and halimadienyl diphosphate, providing novel catalytic insight.
Genetic dereplication driven discovery of a tricinoloniol acid biosynthetic pathway in Trichoderma hypoxylon
Three new sesquiterpene tricinoloniol acids were found by a genetic dereplication approach in combination with coordinated gene expression of biosynthetic gene clusters of tri and tra. The biosynthetic pathway was identified by targeted deletion of terpene cyclase traA.
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.
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.
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.
About this collection
The latest articles published in Organic and Biomolecular Chemistry related to chemical biology research.