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.
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.
Solvent- and catalyst-free transamidation reaction of unprotected glycosyl carboxamides.
Real-time monitoring of a photoactivated hydrogen persulfide donor for biological entities
A visible light responsive H2S2 donor based on the ESIPT mechanism with real-time monitoring ability using a non-invasive fluorescence technique.
Recognition of mixed-sequence DNA targets using spermine-modified Invader probes
Invader probes are additionally activated for recognition of mixed-sequence DNA targets upon incorporation of spermine bulges.
Chemoenzymatic reduction of citreorosein and its implications on aloe-emodin and rugulosin C (bio)synthesis
We report the first chemoenzymatic reduction of citreorosein to putative biosynthetic intermediates which will have implications on aloe-emodin and rugulosin C (bio)synthesis.
Synthesis and application of light-switchable arylazopyrazole rapamycin analogs
The first photoswitchable rapamycin analogs were synthesized and evaluated in split-enzyme assays using FKBP/FRB fusion, revealing configurational specificity of the system.
Triflic acid-mediated synthesis of thioglycosides
Examples include all common hexoses, aminosugars, sialic acids, and disaccharides.
The secondary structure of a heptapeptide containing trifluoromethyl-λ6-tetrafluorosulfanyl substituted amino acids
The polar hydrophobic trifluoromethyl-λ6-tetrafluorosulfanyl (CF3SF4) group effectively induces secondary structure in a heptapeptide in both polar and non-polar solvents.
Compatibility of 5-ethynyl-2′F-ANA UTP with in vitro selection for the generation of base-modified, nuclease resistant aptamers
A nucleoside triphosphate bearing modifications at both the sugar and the nucleobase level was shown to be compatible with combinatorial methods of in vitro selection.
Optimised approach to albumin–drug conjugates using monobromomaleimide-C-2 linkers
Monobromomaleimides with C-2-PEG linkers offer an optimised platform for site-selective albumin conjugation, offering efficient conjugation and accelerated stabilising hydrolysis which prevents loss of drug during construction.
Distortion of mannoimidazole supports a B2,5 boat transition state for the family GH125 α-1,6-mannosidase from Clostridium perfringens
Enzyme transition-state mimics can act as powerful inhibitors and allow structural studies that report on the conformation of the transition-state.
Microcalorimetry and fluorescence show stable peptide nucleic acid (PNA) duplexes in high organic content solvent mixtures
Peptide nucleic acid (PNA) hybridisation is highly tolerant to the addition of organic solvent. This finding suggests that PNA could enable the use of a range of water-sensitive chemistries in nucleic acid templating applications.
Production of a photohexapeptide library from entomopathogenic Photorhabdus asymbiotica PB68.1
A library of new peptides named photohexapeptides was identified from entomopathogenic Photorhabdus asymbiotica PB68.1 after the NRPS-encoding gene phpS was activated via promoter exchange.
Formation of i-motifs from acyclic (L)-threoninol nucleic acids
Acyclic (L)-threoninol nucleic acids ((L)-aTNA) containing poly-cytosines are prepared and investigated at various pH values, revealing the formation of a highly stable structure at lower pH that have the characteristics of an i-motif.
Chemoenzymatic synthesis of the oligosaccharide moiety of the tumor-associated antigen disialosyl globopentaosylceramide
The oligosaccharide of the tumor-associated antigen DSGb5 was synthesized in a chemoenzymatic manner by exploiting the mammalian glycosyl transferases ST3Gal1 and ST6GalNAc5, and its binding with Siglec-7 was investigated by glycan microarray technology.
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.
Extended scaffold glucuronides: en route to the universal synthesis of O-aryl glucuronide prodrugs
An extended scaffold is the key to facile glucuronidation for the synthesis of prodrugs.
A novel chemiluminescent probe for hydrazine detection in water and HeLa cells
A novel chemiluminescent probe based on intramolecular cyclization for hydrazine detection in living cells.
Stereoselective synthesis of unnatural (2S,3S)-6-hydroxy-4-sphingenine-containing sphingolipids
Concise total synthesis of unnatural (2S,3S)-6-hydroxy-4-sphingenine containing sphingolipids using a hydrozirconationtransmetalation reaction and an unusual three-step-one-pot deprotection sequence.
Synthesis and evaluation of photo-activatable β-diarylsydnone-L-alanines for fluorogenic photo-click cyclization of peptides
β-Diarylsydnone-L-alanines were designed and introduced into peptides allowing photo-cyclization only in phosphate containing buffer with concomitant fluorescence generation in live cells.
Fluorescence-labeled neopeltolide derivatives for subcellular localization imaging
Fluorescent-labeled neopeltolide derivatives were rationally designed for cell imaging to elucidate their localization in the mitochondria and the endoplasmic reticulum.
Gold(I)-promoted α-selective sialylation of glycosyl ortho-hexynylbenzoates for the latent-active synthesis of oligosialic acids
A gold(I)-promoted α-selective glycosylation approach with sialyl ortho-hexynylbenzoates as donors is developed for the latent-active synthesis of α-(2 → 9)-linked oligosialic acids.
Photoaffinity palladium reagents for capture of protein–protein interactions
A straightforward strategy using palladium-mediated reagents to reliably incorporate different photoaffinity groups into peptides/proteins for crosslinking of interacting partners is described.
Rational design of a function-based selection method for genetically encoding acylated lysine derivatives
Genetic code expansion depends on the directed evolution of aaRS to recognize non-canonical amino acids. Herein, we reported a function-based method that enables rapidly evolving aaRS for acylated lysine derivatives.
Clostrindolin is an antimycobacterial pyrone alkaloid from Clostridium beijerinckii
A novel antimycobacterial natural product, clostroindolin, was discovered from the anaerobic bacterium Clostridium beijerinckii.
The structure-based traceless specific fluorescence labeling of the smoothened receptor
Inspired by recent progress in structural studies of the smoothened receptor (SMO), a group of affinity probes were developed to specifically light up SMO by grafting a small fluorescent group at the specific residue K395.
Enzymatic synthesis of N-acetyllactosamine from lactose enabled by recombinant β1,4-galactosyltransferases
Synthesis of LacNAc with reversible GalTs.
Copper-mediated anomeric O-arylation with organoboron reagents
Copper-mediated couplings of boroxines with glycosyl hemiacetals generate O-aryl glycosides via Csp2–O bond formation.
Importance of the main chain of lysine for histone lysine methyltransferase catalysis
Enzymatic and computational studies on the simplest lysine analogues that possess a modified main chain demonstrate that the lysine's backbone contributes significantly to functional KMT binding and catalysis.
Robust synthesis of C-terminal cysteine-containing peptide acids through a peptide hydrazide-based strategy
A simple-to-operate and highly efficient strategy for the epimerization-free synthesis of C-terminal Cys-containing peptide acids, which avoids the use of derivatization reagents for resin modification, is developed.
Lacto-N-tetraose synthesis by wild-type and glycosynthase variants of the β-N-hexosaminidase from Bifidobacterium bifidum
Enzymatic lacto-N-biose transfer from lacto-N-biose 1,2-oxazoline to lactose by wild-type and glycosynthase variants of Bifidobacterium bifidum β-N-hexosaminidase yielded lacto-N-tetraose in a single-step, highly regioselective transformation.
The one-pot nonhydrolysis Staudinger reaction and Staudinger or SPAAC ligation
The one-pot nonhydrolysis Staudinger reaction and Staudinger or SPAAC ligation were used for producing a FRET-based dyad in living cells as a proof-of-concept study.
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.
Design of S–S bond containing maleimide-conjugated closo-dodecaborate (SSMID): identification of unique modification sites on albumin and investigation of intracellular uptake
The S–S bond containing maleimide-conjugated closo-dodecaborate (SSMID) was synthesised to identify the binding sites in bovin serum albumin (BSA).
Post-genomic approach based discovery of alkylresorcinols from a cricket-associated fungus, Penicillium soppi
A highly reducing polyketide synthase (HR-PKS) collaborates with a type III PKS to produce alkylresorcinols via unusual biosynthetic machinery.
Development of ergosterol peroxide probes for cellular localisation studies
Cell-permeable ergosterol peroxide probes were synthesized to advance their biological understanding and therapeutic potential.
TuPPL: Tub-tag mediated C-terminal protein–protein-ligation using complementary click-chemistry handles
We introduce a chemoenzymatic strategy for straightforward in vitro generation of C-terminally linked fusion proteins.
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.
Pyrrolidine ring puckering and prolyl amide bond configurations of 2-methyl-allo-hydroxyproline-based dipeptides
Synthesis and conformational studies of C-2 methylated D- and L-allo-hydroxyproline containing dipeptides are described.
A cell-permeant small molecule for the super-resolution imaging of the endoplasmic reticulum in live cells
A simple BODIPY-based small molecule has been identified to selectively label the endoplasmic reticulum for high-resolution imaging with negligible cytotoxicity.
Poloxin-2HT+: changing the hydrophobic tag of Poloxin-2HT increases Plk1 degradation and apoptosis induction in tumor cells
Hydrophobically-tagged Poloxin-2HT+ selectively degrades the tumor target Plk1 and induces apoptosis in tumor cells with higher potency than Poloxin-2HT.
Modular synthesis and immunological evaluation of suspected allergenic galactooligosaccharides
The synthesis of suspected GOS-related allergens using a flexible modular approach and their immunological evaluation are reported.
Glycoconjugate synthesis using chemoselective ligation
Chemoselective ligation of carbohydrates and polypeptides was achieved using an adipic acid dihydrazide cross-linker.
One- and two-photon responsive sulfur dioxide (SO2) donors: a combinatorial drug delivery for improved antibiotic therapy
Light-activated sulfur dioxide donors have been developed and explored their applicability for combinatorial antibiotic therapy with self-monitoring ability.
Cytosporins A–D, novel benzophenone derivatives from the endophytic fungus Cytospora rhizophorae A761
Cytosporins A–D (1–4), hemiterpene-conjugated phenolics with an unprecedented benzo[b][1,5]dioxocane skeleton, were isolated from Cytospora rhizophorae A761.
Stereoselective C-terminal peptide elongation from Chan–Lam–Evans reaction generated isopropenyl esters
Peptide isoprenyl esters were made via the Cu-mediated Chan–Lam–Evans reaction and elongated via pyrazole/DMEP-catalysed aminolysis.
Abinukitrine A, a unique 17,18-cyclolanostane triterpenoid from Abies nukiangensis
Abinukitrine A was isolated from Abies nukiangensis as the first example of 17,18-cyclolanostane. It showed a potent anti-hepatitis C virus effect.
DNA triplex-based fluorescence turn-on sensors for adenosine using a fluorescent molecular rotor 5-(3-methylbenzofuran-2-yl) deoxyuridine
Fluorescence turn-on detection of adenosine based on microenvironmental and conformational changes of a fluorescent molecular rotor in the DNA triplex is reported.
About this collection
The latest articles published in Organic and Biomolecular Chemistry related to chemical biology research.