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Themed collection In Celebration of Andrew D. Hamilton’s Career in Chemistry

42 items
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In celebration of the 60th birthday of Professor Andrew D. Hamilton FRS

An on-line collection of articles celebrating the 60th birthday of Professor Andrew D. Hamilton FRS has been published featuring contributions from students and colleagues past and present.

Graphical abstract: In celebration of the 60th birthday of Professor Andrew D. Hamilton FRS
Perspective

Chemical approaches for detection and destruction of nerve agents

Since the introduction of organophosphorus (OP) compounds as nerve agents and pesticides, methods of dealing with their toxicity to humans have been intensely researched.

Graphical abstract: Chemical approaches for detection and destruction of nerve agents
Perspective

AApeptides as a new class of antimicrobial agents

Herein we describe the development of AApeptides as a new class of peptidomimetics that mimic natural antimicrobial peptides.

Graphical abstract: AApeptides as a new class of antimicrobial agents
Review Article

Peptides: minimal drug surrogates to interrogate and interfere with protein function

The interactome in normal and disease cells is a key area for study and therapeutic targeting, yet few molecules have been developed that can interfere with protein–protein interactions within cells. Peptides and homologues are potential reagents to target PPI.

Graphical abstract: Peptides: minimal drug surrogates to interrogate and interfere with protein function
Communication

Changes in lipid density induce membrane curvature

Highly curved bilayer lipid membranes make up the shell of many intra- and extracellular compartments, including organelles and vesicles. Using all-atom molecular dynamics simulations, we show that increasing the density of lipids in the bilayer membrane can induce the membrane to form a curved shape.

Graphical abstract: Changes in lipid density induce membrane curvature
Communication

Influence of achiral units with gem-dimethyl substituents on the helical character of aliphatic oligourea foldamers

The structures of various urea oligomers incorporating one or two central achiral 1,2-diamino-1,1-dimethylethane (DADME) units have been investigated in solution and in the crystalline state.

Graphical abstract: Influence of achiral units with gem-dimethyl substituents on the helical character of aliphatic oligourea foldamers
Communication

Storable palladacycles for selective functionalization of alkyne-containing proteins

We report facile preparation of palladacycles as storable arylpalladium(II) reagents from acetanilides via cyclopalladation. The palladacycles exhibited good stability in PBS buffer and were capable of functionalizing a metabolically encoded HPG-containing protein, thus providing a new type of biocompatible organometallic reagent for selectively functionalizing the alkyne-encoded proteins.

Graphical abstract: Storable palladacycles for selective functionalization of alkyne-containing proteins
Communication

Diverse topologies in dynamic combinatorial libraries from tri- and mono-thiols in water: sensitivity to weak supramolecular interactions

We describe here the use of disulfide exchange reactions to generate distinct supramolecular topologies within a dynamic combinatorial library (DCL) derived from tri- and mono-functionalised thiol components in water.

Graphical abstract: Diverse topologies in dynamic combinatorial libraries from tri- and mono-thiols in water: sensitivity to weak supramolecular interactions
Communication

Antimicrobial N-(2-chlorobenzyl)-substituted hydroxamate is an inhibitor of 1-deoxy-D-xylulose 5-phosphate synthase

A simple hydroxamate, derived from hydrolysis of ketoclomazone, was found to inhibit Haemophilus influenzae 1-deoxy-D-xylulose 5-phosphate synthase at the low μM range and suppress bacterial growth.

Graphical abstract: Antimicrobial N-(2-chlorobenzyl)-substituted hydroxamate is an inhibitor of 1-deoxy-d-xylulose 5-phosphate synthase
Communication

Towards a dynamic covalent molecular switch: substituent effects in chalcone/flavanone isomerism

Chalcone/flavanone interconversion occurs facilely under aqueous alkaline conditions making it a promising scaffold for the development of a covalent molecular switch.

Graphical abstract: Towards a dynamic covalent molecular switch: substituent effects in chalcone/flavanone isomerism
Communication

A foldamer approach to targeting membrane bound helical states of islet amyloid polypeptide

A small molecule, protein mimetic based approach is shown to specifically inhibit lipid catalysed self-assembly of islet amyloid polypeptide (IAPP).

Graphical abstract: A foldamer approach to targeting membrane bound helical states of islet amyloid polypeptide
Communication

Controllable self-assembly of amphiphilic macrocycles into closed-shell and open-shell vesicles, nanotubes, and fibers

Two structurally similar amphiphilic macrocycles differing in functional groups self-assemble into closed-shell and open-shell vesicles in polar solvents and morph into nanotubes and fibers upon acidification.

Graphical abstract: Controllable self-assembly of amphiphilic macrocycles into closed-shell and open-shell vesicles, nanotubes, and fibers
Communication

Synthesis of peptoid based small molecular gelators by a multiple component reaction

Novel tripeptoid gelators are synthesized by a one-pot Ugi reaction from simple starting materials.

Graphical abstract: Synthesis of peptoid based small molecular gelators by a multiple component reaction
Communication

Quantitative detection of single base mutation by combining PNA hybridization and MALDI-TOF mass analysis

Peptide nucleic acid (PNA) probes were designed to bind to the internal reference sequence and the single base mutation sequence within PCR-amplified DNA templates, and the PNA probes were quantitatively analyzed with MALDI-TOF mass spectrometry.

Graphical abstract: Quantitative detection of single base mutation by combining PNA hybridization and MALDI-TOF mass analysis
Communication

Complete shift of ferritin oligomerization toward nanocage assembly via engineered proteinprotein interactions

A straight-forward computational method is used to redesign protein–protein interfaces of a dimorphic nanocage forcing it to assemble with monomorphism.

Graphical abstract: Complete shift of ferritin oligomerization toward nanocage assembly via engineered protein–protein interactions
Communication

Monitoring the HIV-1 integrase enzymatic activity using atomic force microscopy in a 2LTR system

Partial and full integration products were observed using AFM in a 2LTR system.

Graphical abstract: Monitoring the HIV-1 integrase enzymatic activity using atomic force microscopy in a 2LTR system
Communication

Resonance-assisted hydrogen bonding induced nucleophilic addition to hamper ESIPT: ratiometric detection of cyanide in aqueous media

For ratiometric “naked eye” detection of CN, an ESIPT exhibiting benzothiazole receptor (BHI) is designed having one aldehyde group ortho and the other aldehyde para to the OH group respectively.

Graphical abstract: Resonance-assisted hydrogen bonding induced nucleophilic addition to hamper ESIPT: ratiometric detection of cyanide in aqueous media
Communication

Novel pH responsive calix[8]arene hydrogelators: self-organization processes at a nanometric scale

Water soluble amphiphilic calix[8]arenes form pH-responsive and reversible supramolecular hydrogels; depending on their functionalization, pH variations trigger hydrogelation under basic or acidic conditions.

Graphical abstract: Novel pH responsive calix[8]arene hydrogelators: self-organization processes at a nanometric scale
Communication

Supramolecular hydrogels based on bola-amphiphilic glycolipids showing color change in response to glycosidases

This communication describes supramolecular hydrogels exhibiting color change in response to glycosidases, which was successfully employed to construct a colorimetric sensor array chip for rapid detection of glycosidases.

Graphical abstract: Supramolecular hydrogels based on bola-amphiphilic glycolipids showing color change in response to glycosidases
Communication

1,3,5-Trisubstituted benzenes as fluorescent photoaffinity probes for human carbonic anhydrase II capture

The synthesis of small molecule based 1,3,5-trisubstituted benzenes for photo-mediated capture of human carbonic anhydrase II with visualisation by fluorescence is described.

Graphical abstract: 1,3,5-Trisubstituted benzenes as fluorescent photoaffinity probes for human carbonic anhydrase II capture
Concise Article

Exploring novel strategies for AIDS protozoal pathogens: α-helix mimetics targeting a key allosteric proteinprotein interaction in C. hominis thymidylate synthase-dihydrofolate reductase (TS-DHFR)

The bifunctional enzyme TS–DHFR from Cryptosporidium hominis is a molecular target for design of antiparasitic therapies for AIDS-related opportunistic infections.

Graphical abstract: Exploring novel strategies for AIDS protozoal pathogens: α-helix mimetics targeting a key allosteric protein–protein interaction in C. hominis thymidylate synthase-dihydrofolate reductase (TS-DHFR)
Concise Article

Identification of a potent salicylic acid-based inhibitor of tyrosine phosphatase PTP1B

A screen of a library of diverse small-molecules against a subset of phosphatases identified 7b and 7c, which potently inhibit TC-PTP, PTPσ and PTP1B with no inhibition of PTP-LAR, PRL2 A/S, MKPX or papain.

Graphical abstract: Identification of a potent salicylic acid-based inhibitor of tyrosine phosphatase PTP1B
Concise Article

N-substituted sultam carboxylic acids as novel glycogen synthase activators

We discovered a novel class of N-substituted sultam carboxylic acids as potent glycogen synthase activators with cellular activity and oral bioavailability.

Graphical abstract: N-substituted sultam carboxylic acids as novel glycogen synthase activators
Concise Article

Design, synthesis and biological evaluation of novel ligustrazinylated derivatives as potent cardiovascular agents

A series of novel ligustrazinylated derivatives was designed, synthesized and evaluated for their platelet aggregation inhibition and protective effect on injured ECV-304 cells.

Graphical abstract: Design, synthesis and biological evaluation of novel ligustrazinylated derivatives as potent cardiovascular agents
Paper

Major mechanistic differences between the reactions of hydroxylamine with phosphate di- and tri-esters

Hydroxylamine reacts with the diester anion DPP by the expected concerted SN2(P) mechanism, but with the triester TPP by an addition–elimination process, with breakdown of the phosphorane intermediate rate-determining.

Graphical abstract: Major mechanistic differences between the reactions of hydroxylamine with phosphate di- and tri-esters
Paper

Discovery of N-(4-sulfamoylphenyl)thioureas as Trypanosoma brucei leucyl-tRNA synthetase inhibitors

We report the discovery of N-(4-sulfamoylphenyl)thioureas as a new class of T. brucei LeuRS inhibitors.

Graphical abstract: Discovery of N-(4-sulfamoylphenyl)thioureas as Trypanosoma brucei leucyl-tRNA synthetase inhibitors
Paper

Synthesis and biological activity of phosphoglycolipids from Thermus thermophilus

Unique glycolipids from an extreme thermophile, Thermus thermophilus, were synthesized for the first time, with newly developed glycosylation methods.

Graphical abstract: Synthesis and biological activity of phosphoglycolipids from Thermus thermophilus
Paper

New meso-substituted trans-A2B2 di(4-pyridyl)porphyrins as building blocks for metal-mediated self-assembling of 4 + 4 Re(I)–porphyrin metallacycles

An optimized high-yield synthesis of meso-arylsubstituted trans-A2B2 di(4-pyridyl)porphyrins and their use as building blocks in the Re(I)-mediated self-assembling of square metallacycles are presented.

Graphical abstract: New meso-substituted trans-A2B2 di(4-pyridyl)porphyrins as building blocks for metal-mediated self-assembling of 4 + 4 Re(i)–porphyrin metallacycles
Paper

An efficient chemical synthesis of carboxylate-isostere analogs of daptomycin

Herein we report a direct and efficient method for the synthesis of four new carboxylate-isostere analogs of daptomycin.

Graphical abstract: An efficient chemical synthesis of carboxylate-isostere analogs of daptomycin
Paper

Meta-analysis in asymmetric catalysis. Influence of chelate geometry on the roles of PN chelating ligands

Analysis of X-ray crystal structures for families of PN ligands reveal conformational variations that can be linked to trends in catalytic asymmetric synthesis.

Graphical abstract: Meta-analysis in asymmetric catalysis. Influence of chelate geometry on the roles of PN chelating ligands
Paper

Structural modifications of (Z)-3-(2-aminoethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione that improve selectivity for inhibiting the proliferation of melanoma cells containing active ERK signaling

Cell-based SAR of an ERK docking domain inhibitor

Graphical abstract: Structural modifications of (Z)-3-(2-aminoethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione that improve selectivity for inhibiting the proliferation of melanoma cells containing active ERK signaling
Paper

Four-component assembly in the crystalline state driven by amidinium–carboxylate salt bridge formation from an aqueous solution

The introduction of two amidinium groups to the 1,8-position of a spacer unit can control the direction of formation of a self-assembled structure and succeeded in the formation of a four-component assembled structure .

Graphical abstract: Four-component assembly in the crystalline state driven by amidinium–carboxylate salt bridge formation from an aqueous solution
Paper

One-shot preparation of an inherently chiral trifunctional calix[4]arene from an easily available cone-triformylcalix[4]arene

An inherently chiral ABCH-substituted cone-calix[4]arene derivative has been prepared in a one-step process starting from the easily available cone-triformylcalix[4]arene.

Graphical abstract: One-shot preparation of an inherently chiral trifunctional calix[4]arene from an easily available cone-triformylcalix[4]arene
Paper

Peptide inhibitors of the Keap1–Nrf2 proteinprotein interaction with improved binding and cellular activity

We describe potent peptide conjugate inhibitors of the Keap1–Nrf2 protein–protein interaction that have activity in cell based Nrf2 induction assays.

Graphical abstract: Peptide inhibitors of the Keap1–Nrf2 protein–protein interaction with improved binding and cellular activity
Paper

Silanization of quartz, silicon and mica surfaces with light-driven molecular motors: construction of surface-bound photo-active nanolayers

The attachment of molecular rotary motors containing triethoxysilane functional groups to quartz, silicon and mica surfaces is described and the effect of photochemical and thermal isomerization steps on the surface assemblies was studied.

Graphical abstract: Silanization of quartz, silicon and mica surfaces with light-driven molecular motors: construction of surface-bound photo-active nanolayers
Paper

Subtle “supramolecular buttressing effects” in Cucurbit[7]uril/guest assemblies

“Supramolecular buttressing” was defined as the alteration, by a neighboring unit, of a substituent effect on intermolecular recognition, and was assessed using Cucurbit[7]uril–guest assemblies.

Graphical abstract: Subtle “supramolecular buttressing effects” in Cucurbit[7]uril/guest assemblies
Paper

Polyhydroxylated pyrrolizidine alkaloids from transannular iodoaminations: application to the asymmetric syntheses of (−)-hyacinthacine A1, (−)-7a-epi-hyacinthacine A1, (−)-hyacinthacine A2, and (−)-1-epi-alexine

Transannular iodoamination of substituted 1,2,3,4,7,8-hexahydroazocines facilitates the asymmetric synthesis of polyhydroxylated pyrrolizidine alkaloids.

Graphical abstract: Polyhydroxylated pyrrolizidine alkaloids from transannular iodoaminations: application to the asymmetric syntheses of (−)-hyacinthacine A1, (−)-7a-epi-hyacinthacine A1, (−)-hyacinthacine A2, and (−)-1-epi-alexine
Paper

Reaction-based dual signaling of fluoride ions by resorufin sulfonates

Resorufin nosylate exhibited naked-eye detectable colorimetric and fluorogenic signaling of fluoride ions in acetonitrile. The interference from sulfide ions was effectively suppressed by using the TPEN–Cu2+ complex as a masking agent.

Graphical abstract: Reaction-based dual signaling of fluoride ions by resorufin sulfonates
Paper

Dual signaling of hydrazine by selective deprotection of dichlorofluorescein and resorufin acetates

Highly selective chemosignaling behaviors toward hydrazine of a reaction-based probe of dichlorofluorescein and resorufin acetates were investigated. Hydrazinolysis of latent dichlorofluorescein and resorufin acetates revealed prominent chromogenic and fluorogenic signaling.

Graphical abstract: Dual signaling of hydrazine by selective deprotection of dichlorofluorescein and resorufin acetates
Paper

Sequential enantiodivergent organocatalysis: reversibility in enantioswitching controlled by a conformationally flexible guanidine/bisthiourea organocatalyst

Here we describe our studies on solvent-dependent enantiodivergent Mannich-type reactions utilizing conformationally flexible guanidine/bisthiourea organocatalyst (S,S)-1.

Graphical abstract: Sequential enantiodivergent organocatalysis: reversibility in enantioswitching controlled by a conformationally flexible guanidine/bisthiourea organocatalyst
Open Access Paper

Protein destabilisation by ruthenium(II) tris-bipyridine based protein-surface mimetics

A ruthenium(II) tris-chelate perturbs the folding landscape of its target protein leading to lowered melting temperatures and accelerated proteolysis.

Graphical abstract: Protein destabilisation by ruthenium(ii) tris-bipyridine based protein-surface mimetics
Paper

A rotaxane host system containing integrated triazole C–H hydrogen bond donors for anion recognition

A novel bis-triazole pyridinium axle containing rotaxane, prepared by a chloride anion templated ring closing metathesis clipping strategy, exhibits selectivity for halide anions over oxoanions with a notable preference for bromide being shown amongst the halides.

Graphical abstract: A rotaxane host system containing integrated triazole C–H hydrogen bond donors for anion recognition
From the themed collection: In celebration of Paul Beer’s 60th Birthday
42 items

About this collection

We are delighted to present this collection of articles that have been dedicated to Professor Andrew D. Hamilton FRS, on the occasion of his 60th birthday. Featuring contributions from students and colleagues past and present, and an introductory Profile article by guest-editors Sam Thompson and Andrew J. Wilson, with the contribution of Sir Alan R. Battersby.

We hope you enjoy the collection!

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