Themed collection Chemical Biology in OBC
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.
Molecular platforms based on biocompatible photoreactions for photomodulation of biological targets
In this paper, we summarize molecular platforms based on ultraviolet (UV), visible (Vis) or near-infrared (NIR) photoreactions. Recent applications for spatiotemporal photomodulation of various biomolecules in living objects are also discussed.
Photoaffinity labelling strategies for mapping the small molecule–protein interactome
We review the development of photoaffinity labeling (PAL) chemistries and the application of PAL to chemoproteomic target deconvolution for small molecules, lipids, and metabolites.
Antitumor activity of tridentate pincer and related metal complexes
Pincer and related metal complexes containing tunable tridentate ligand frameworks display promising antitumor activity.
Optically superior fluorescent probes for selective imaging of cells, tumors, and reactive chemical species
Fluorescent probes with superior optical properties have been summarized along with the mechanisms used for their development and the challenges faced in their synthesis.
Asparaginyl endopeptidases: enzymology, applications and limitations
The potentials of using asparaginyl endopeptidases (AEP) as tools for polypeptide modifications have been discussed.
Chemical probes targeting the kinase CK2: a journey outside the catalytic box
An up-to-date and comprehensive review on chemical probes targeting the important kinase CK2.
Approaches for peptide and protein cyclisation
Polypeptide cyclisation can enhance thermal stability, proteolytic resistance and membrane permeability. Cyclisation can be achieved by methods including chemical, enzyme and protein tag approaches. Each has strengths and limitations.
Harnessing methylation and AdoMet-utilising enzymes for selective modification in cascade reactions
This review summarizes the recent findings and developments in the emerging area of (chemo)-enzymatic cascades using MTases and AdoMet-generating enzymes.
Metabolic labeling probes for interrogation of the host–pathogen interaction
Metabolic labeling of intracellular pathogens can provide new methods of studying host pathogen interactions.
Chemistry and biology of spiroacetals from myxobacteria
This review details the isolation, biosynthesis, biological activity and synthesis of spiroacetals from the myxobacterium Sorangium cellulosum.
Artificial enzymes bringing together computational design and directed evolution
This manuscript reviews the combination of computational enzyme design and directed evolution and its advantages in the development of artificial enzymes.
Silicon phthalocyanines: synthesis and resurgent applications
Their unique axial bonds and NIR optical properties have made silicon phthalocyanines (SiPcs) valuable compounds. Herein, we present key synthetic strategies and emerging applications of SiPcs over the past decade.
Recent advances in the direct O-arylation of carbohydrates
An emerging approach for the synthesis of O-aryl glycosides and carbohydrate-derived aryl ethers via C(sp2)–O bond formation is reviewed.
Recent highlights of biosynthetic studies on marine natural products
Marine bacteria are excellent yet often underexplored sources of structurally unique bioactive natural products.
Glycosyl disulfides: importance, synthesis and application to chemical and biological systems
This review explores methodologies for the preparation of glycosyl disulfides, their utility as intermediates in carbohydrate synthesis, and evaluates their biological impact in glycoscience and beyond.
Tyrosine bioconjugation – an emergent alternative
A review of the heretofore less explored approach of tyrosine bioconjugation, which is rapidly becoming a constructive alternative/complement to the more well-established strategies, is provided.
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.
A comprehensive study on the effect of backbone stereochemistry of a cyclic hexapeptide on membrane permeability and microsomal stability
The effect of backbone stereochemistry of a cyclic hexapeptide on membrane permeability and metabolic stability was comprehensively evaluated. Besides, the effect of side chain structures on the pharmacokinetic properties was investigated.
Synthesis, proteolytic stability, and in vitro evaluation of DOTA conjugated p160 peptide based radioconjugates: [177Lu]Lu–DOTA–p160
Synthesis, spectroscopic characterization, and in vitro biological evaluation of Lu-177 radiolabeled DOTA conjugated p160 peptide derivatives: potential candidates for breast tumor imaging and therapy.
Pentacyclic spermidine alkaloids with radioprotective and anti-inflammatory activities from Orychophragmus violaceus
Two pairs of novel pentacyclic spermidine alkaloid enantiomers, (±)-orychoviolines A and B, were isolated from the seeds of Orychophragmus violaceus and represented the first example of a 2-piperidinone-fused hydrodibenzofuran skeleton.
Automated glycan assembly of peptidoglycan backbone fragments
The automated glycan assembly of different oligosaccharide fragments of the bacterial peptidoglycan backbone is reported.
Perforalactones D and E, two new C-20 quassinoids with potential activity to induce lysosomal biogenesis from the twigs of Harrisonia perforata (Blanco) Merr.
Two new quassinoids, perforalactones D and E, from Harrisonia perforata, could promote the expression of lysosomal genes and induce lysosomal biogenesis.
Streptomyces aureorectus DSM 41692 and Streptomyces virens DSM 41465 are producers of the antibiotic nucleocidin and 4′-fluoroadenosine is identified as a co-product
Genome homologies led to the identification of Streptomyces aureorectus DSM 41692 and Streptomyces virens DSM 41465 as producers of the antibiotic nucleocidin, and also 4’-fluoroadenosine.
Methyl to trifluoromethyl substitution as a strategy to increase the membrane permeability of short peptides
CH3 to CF3 substitution on a side chain of proteiogenic amino acids increases the membrane permeability of peptides.
Solitumergosterol A, a unique 6/6/6/6/5 steroid from the deep-sea-derived Penicillium solitum MCCC 3A00215
An unprecedented C30 steroid, solitumergosterol A (1), from the deep-sea-derived Penicillium solitum inhibited the proliferation of MB231 tumor cells by a RXRα-dependent mechanism.
Inhibition of efflux pumps aids small-molecule probe-based fluorescence labeling and imaging in the Gram-negative bacterium Escherichia coli
We describe a novel strategy for small-molecule probe-based fluorescence protein labeling and imaging in the Gram-negative bacterium Escherichia coli, which involves inhibition of efflux pumps.
Tightly linked morpholino-nucleoside chimeras: new, compact cationic oligonucleotide analogues
The synthesis of oligonucleotide analogues consisting of morpholino and a ribo- or deoxyribonucleoside in which the 5'-amino group of the nucleoside unit provides the nitrogen to the morpholine ring is described.
Stereochemical characterisation of the non-canonical α-humulene synthase from Acremonium strictum
The stereochemical course of the non-canonical α-humulene synthase from Acremonium strictum was investigated in isotopic labelling experiments.
Pyrrovobasine, hybrid alkylated pyrraline monoterpene indole alkaloid pseudodimer discovered using a combination of mass spectral and NMR-based machine learning annotations
The MS2-guided phytochemical investigation of Voacanga africana stem bark resulted in the isolation of pyrrovobasine, the first pyrraline-containing MIA.
A silyl ether-protected building block for O-GlcNAcylated peptide synthesis to enable one-pot acidic deprotection
In this report, we introduce a novel building block for Fmoc/tBu solid phase peptide synthesis (SPPS) of β-linked O-GlcNAcylated peptides.
A triple-targeting delivery system carrying two anticancer agents
To improve tumor selectivity, we prepared a new triple-targeting delivery system bearing two anticancer agents. Both anticancer agents in this system are released in the presence of both H2O2 and cathepsin B which are highly produced in cancer cells.
Protecting carbohydrates with ethers, acetals and orthoesters under basic conditions
Chlorinated ethyl and vinyl ethers are introduced at various positions of carbohydrates and gives access to acetals and ortho-esters under basic conditions.
Controlled density glycodendron microarrays for studying carbohydrate–lectin interactions
Density depended binding and selectivity is studied on glycodendron microarray with defined valency, which were prepared by on-chip synthesis and analysed by in situ MALDI-TOF MS.
Rational design and development of a lit-active photoswitchable inhibitor targeting CENP-E
Lit-active (cis-active) photoswitchable inhibitor targeting centromere-associated protein E (CENP-E) was developed through the rational design.
Synthesis of enantiopure α-Tfm-proline and α-Tfm-pipecolic acid from oxazolo-pyrrolidines and -piperidines
Scalable synthesis of enantiopure (R) and (S)-α-Tfm-proline and α-Tfm-pipecolic acid.
About this collection
The latest articles published in Organic and Biomolecular Chemistry related to chemical biology research.