Themed collection Organic & Biomolecular Chemistry 10th Anniversary
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Welcome to the 10th anniversary issue of Organic & Biomolecular Chemistry
Introducing the 10th anniversary issue of Organic & Biomolecular Chemistry.
Org. Biomol. Chem., 2012,10, 5683-5683
https://doi.org/10.1039/C2OB90091B
Methylthioxylose – a jewel in the mycobacterial crown?
The discovery of methylthioxylose and studies toward understanding its origins and biological roles.
Org. Biomol. Chem., 2012,10, 5698-5706
https://doi.org/10.1039/C2OB25630D
Organic reactivity in liquid ammonia
Liquid ammonia is a useful solvent for many organic reactions including aliphatic and nucleophilic substitution reactions and has the potential to replace conventional dipolar aprotic solvents in a range of reactions.
Org. Biomol. Chem., 2012,10, 5732-5739
https://doi.org/10.1039/C2OB25064K
“Frustrated Lewis pair” hydrogenations
This perspective article discusses developments of metal-free hydrogenation catalysts derived from “frustrated Lewis pair” (FLP) systems.
Org. Biomol. Chem., 2012,10, 5740-5746
https://doi.org/10.1039/C2OB25339A
Chemical and semisynthesis of posttranslationally modified proteins
Recent advances in chemical and semisynthesis of proteins are becoming increasingly instrumental to prepare homogeneous posttranslationally modified proteins for biochemical and structural analyses. Here, we survey these efforts and their importance in dissecting the role of several posttranslational modifications on various proteins.
Org. Biomol. Chem., 2012,10, 5684-5697
https://doi.org/10.1039/C2OB25149C
Peptide and peptidomimetic ligands for CXC chemokine receptor 4 (CXCR4)
This perspective article highlights the recent developments of peptide and peptidomimetic ligands for CXC chemokine receptor 4 (CXCR4).
Org. Biomol. Chem., 2012,10, 5720-5731
https://doi.org/10.1039/C2OB25107H
A unified access to diverse heteroaromatic scaffolds using the radical chemistry of xanthates
The radical addition of xanthates to alkenes provides a practical and flexible entry to a broad variety of heteroaromatic structures.
Org. Biomol. Chem., 2012,10, 5707-5719
https://doi.org/10.1039/C2OB25169H
New H-bonding patterns in biphenyl -based synthetic lectins; pyrrolediamine bridges enhance glucose-selectivity
A new synthetic lectin features pyrroles and amines as polar binding units. In aqueous buffer, glucose is bound selectively over all other tested carbohydrates.
Org. Biomol. Chem., 2012,10, 5760-5763
https://doi.org/10.1039/C2OB25900A
Conotoxin engineering: dual pharmacophoric noradrenaline transport inhibitor /integrin binding peptide with improved stability
The synthesis, biological activity and pharmacokinetics of a stable cyclic conotoxin with two independent pharmacophores are described.
Org. Biomol. Chem., 2012,10, 5791-5794
https://doi.org/10.1039/C2OB25133G
Sym-(CH2X)5-corannulenes: molecular pentapods displaying functional group and bioconjugate appendages
Pentapodal ω-functional derivatives of corannulene have been synthesized from sym-pentachlorocorannulene by iron-catalyzed aryl–alkyl cross coupling reactions.
Org. Biomol. Chem., 2012,10, 5799-5802
https://doi.org/10.1039/C2OB25503K
Development of strong Brønsted base catalysis: catalytic direct-type Mannich reactions of non-activated esters via a product-base mechanism
A catalytic Mannich reaction of a simple ester with no activating functionality at the α-position via a product-base mechanism was reported.
Org. Biomol. Chem., 2012,10, 5750-5752
https://doi.org/10.1039/C2OB25522G
Self condensation of enamines mediated by acetylation . A novel approach to 1-(azol-5-yl)-(1E,3Z)-butadiene-4-N,N-dimethylamines
Novel self-condensation of 3-(azol-5-yl)-1,1-dimethylenamines has been found to form new C–C bonds leading to 2,4-(1,2,3-triazole-1,2,3-thiadiazole-3-phenylisothiazole)-(1E,3Z)-5-yl-butadiene-1-amines.
Org. Biomol. Chem., 2012,10, 5795-5798
https://doi.org/10.1039/C2OB25331C
Flow synthesis using gaseous ammonia in a Teflon AF-2400 tube-in-tube reactor: Paal–Knorr pyrrole formation and gas concentration measurement by inline flow titration
Permeation of ammonia through Teflon AF-2400 (which is temperature and solvent dependent) facilitated the continuous flow Paal–Knorr synthesis of pyrroles.
Org. Biomol. Chem., 2012,10, 5774-5779
https://doi.org/10.1039/C2OB25407G
Synthesis of 1,2,4-triazines and the triazinoisoquinolinedione DEF ring system of noelaquinone
The intramolecular Staudinger-aza-Wittig reaction was used for the first preparation of the DEF ring system of noelaquinone.
Org. Biomol. Chem., 2012,10, 5811-5814
https://doi.org/10.1039/C2OB25353D
Amphiphilic α-helix mimetics based on a benzoylurea scaffold
The design and synthesis of conformationally constrained amphiphilic benzoylurea α-helix mimetics is described.
Org. Biomol. Chem., 2012,10, 5780-5782
https://doi.org/10.1039/C2OB25273B
Photochemical oxazole –nitrile conversion downstream of rhizoxin biosynthesis and its impact on antimitotic activity
In the endofungal bacterium Burkholderia rhizoxinica novel rhizoxin derivatives with unusual nitrile substitutions are formed by a rare photochemical transformation.
Org. Biomol. Chem., 2012,10, 5756-5759
https://doi.org/10.1039/C2OB25250C
Selective thioether macrocyclization of peptides having the N-terminal 2-chloroacetyl group and competing two or three cysteine residues in translation
The mode of thioether macrocyclization of peptides containing an N-terminal 2-chloroacetyl group and two or three competing cysteine residues at downstream positions has been extensively studied, leading to a strategy for designated formation of overlapping-bicyclic peptides or dumbbell-type bicyclic peptides.
Org. Biomol. Chem., 2012,10, 5783-5786
https://doi.org/10.1039/C2OB25306B
Synthesis and structure–activity relationships of o-sulfonamido-arylhydrazides as inhibitors of LL-diaminopimelate aminotransferase (LL-DAP-AT)
The synthesis of a series of o-sulfonamido-arylhydrazides and their activity as inhibitors of LL-diaminopimelic acid aminotransferase are described.
Org. Biomol. Chem., 2012,10, 5815-5819
https://doi.org/10.1039/C2OB00040G
Facile air-oxidation of large aromatic hydrocarbon bay regions to bay region quinones : predicted oxygen-sensitivity of hydrogen-terminated carbon nanotubes
The ease with which dimesitylbisanthene oxidizes in air to the corresponding bay region quinone is seen as a warning that hydrogen-terminated carbon nanotubes having bay regions on their rims may be highly sensitive to air oxidation.
Org. Biomol. Chem., 2012,10, 5747-5749
https://doi.org/10.1039/C2OB25208B
Short polyglutamine peptide forms a high-affinity binding site for thioflavin-T at the N-terminus
We report the first observation of direct molecular contacts between ThT and model peptide aggregates by applying solid-state NMR spectroscopy.
Org. Biomol. Chem., 2012,10, 5787-5790
https://doi.org/10.1039/C2OB07157F
Reactions of triflate esters and triflamides with an organic neutral super-electron-donor
The bis-pyridinylidene 13 converts aliphatic and aryl triflate esters to the corresponding alcohols and phenols respectively, using DMF as solvent, generally in excellent yields.
Org. Biomol. Chem., 2012,10, 5807-5810
https://doi.org/10.1039/C2OB25116G
Convergent diastereoselective preparation of adjacent quaternary stereocenters in an acyclic system
The combined carbometalation–zinc homologation–allylation reaction with ketones allows the preparation of allylic vicinal diol derivatives possessing two adjacent quaternary centers in an acyclic system through the concomitant formation of three new carbon-carbon bonds in a single-pot operation..
Org. Biomol. Chem., 2012,10, 5803-5806
https://doi.org/10.1039/C2OB25121C
Tuning and predicting biological affinity: aryl nitriles as cysteine protease inhibitors
The influence of the electrophilicity of aromatic nitriles on cysteine protease inhibition and cytotoxicity was investigated. Calculations were used to obtain nitrile electrophilicities, revealing a clear correlation with biological affinity.
Org. Biomol. Chem., 2012,10, 5764-5768
https://doi.org/10.1039/C2OB00034B
Observation of neighboring ortho-hydroxyl group participation in organocatalytic asymmetric sequential Michael-lactonization reactions: synthesis of highly substituted chiral spirodihydrocoumarins
A general approach to the asymmetric synthesis of spirodihydrocoumarins with a quaternary stereocenter was achieved through a favoured 21-membered supramolecular transition state using sequential Michael and lactonization reactions.
Org. Biomol. Chem., 2012,10, 5825-5829
https://doi.org/10.1039/C2OB07122C
A general electron transfer reduction of lactones using SmI2–H2O
A selective method for the reduction of lactones of all ring sizes and topologies using SmI2–H2O and a Lewis base is described.
Org. Biomol. Chem., 2012,10, 5820-5824
https://doi.org/10.1039/C2OB00017B
The direct catalytic asymmetric aldol reaction of α-substituted nitroacetates with aqueous formaldehyde under base-free neutral phase-transfer conditions
Enantioselective direct aldol reaction of α-substituted nitroacetates with aqueous formaldehyde has been achieved under base-free neutral phase-transfer conditions.
Org. Biomol. Chem., 2012,10, 5753-5755
https://doi.org/10.1039/C2OB07193B
Water-soluble, deep-red fluorescent squaraine rotaxanes
Squaraine rotaxanes with four large stopper groups attached to the ends of the encapsulated squaraine are excellent fluorescent tracers with rapid renal clearance and very low tissue uptake in living mice.
Org. Biomol. Chem., 2012,10, 5769-5773
https://doi.org/10.1039/C2OB06783H
Chemoselective Staudinger-phosphite reaction of symmetrical glycosyl-phosphites with azido-peptides and polygycerols
In this paper we present the synthesis of glyco-phosphoramidate conjugates as easily accessible analogs of glyco-phosphorous esters via the Staudinger-phosphite reaction.
Org. Biomol. Chem., 2012,10, 6211-6216
https://doi.org/10.1039/C2OB25207D
Reactive intermediates in the H-phosphonate synthesis of oligonucleotides
The formation of H-phosphonate diesters is an important step in the synthesis of oligonucleotides.
Org. Biomol. Chem., 2012,10, 5940-5947
https://doi.org/10.1039/C2OB07130D
Ionization state of the catalytic dyad Asp25/25′ in the HIV-1 protease: NMR studies of site-specifically 13C labelled HIV-1 protease prepared by total chemical synthesis
Total chemical synthesis was used to site-specifically 13C-label active site Asp25 and Asp25′ residues in HIV-1 protease and in several chemically synthesized analogues of the enzyme molecule.
Org. Biomol. Chem., 2012,10, 5887-5891
https://doi.org/10.1039/C2OB25569C
Formation of luminescent terbium(III) self-assemblies from pyridyl bis-amidothioureas based ligands in MeOH and in water –DMSO solutions and their use in anion sensing application
The self-assembly formation between the bis amidothiourea ligands 1 and 2 with Tb(III) is described. These give rise to Tb(III) centred emission which is affected upon binding of these to anions such as acetate and phosphate.
Org. Biomol. Chem., 2012,10, 6069-6073
https://doi.org/10.1039/C2OB25720C
New parasite inhibitors encompassing novel conformationally-locked 5′-acyl sulfamoyl adenosines
3′-endo-Sugar-locked 5′-acyl sulfamoyl adenosines inhibit Trypanosoma and Leishmania with IC50s of 0.25–0.51 μM.
Org. Biomol. Chem., 2012,10, 6121-6129
https://doi.org/10.1039/C2OB25879J
Vinyl-triphenylamine dyes, a new family of switchable fluorescent probes for targeted two-photon cellular imaging: from DNA to protein labeling
A new family of nonlinear fluorescent probes for specific DNA or protein labeling was designed by structure space exploration around the vinyl-triphenylamine core.
Org. Biomol. Chem., 2012,10, 6054-6061
https://doi.org/10.1039/C2OB25515D
Synthesis of isoxazoles en route to semi-aromatized polyketides : dehydrogenation of benzonitrile oxide –para-quinone acetal cycloadducts
A facile access has been developed to highly functionalized polycyclic isoxazoles, suitable intermediates for the synthesis of semi-aromatized polyketides, via a two-step protocol including regioselective 1,3-dipolar cycloaddition and MnO2-mediated dehydrogenation.
Org. Biomol. Chem., 2012,10, 6003-6009
https://doi.org/10.1039/C2OB25423A
Helical self-assembly and co-assembly of fluorinated, preorganized discotics
Fluorinated bipyridine discotics self-assemble into stable helical columnar mesophases and alternating helical assemblies with hydrocarbon bipyridine discotics in fluorinated media.
Org. Biomol. Chem., 2012,10, 5898-5908
https://doi.org/10.1039/C2OB25385B
Preferential extraction of left- or right-handed single-walled carbon nanotubes by use of chiral diporphyrin nanotweezers
The 2,6-pyridylene-bridged chiral diporphyrin nanotweezers recognise handedness and diameter of SWNTs simultaneously and independently, yielding optically active SWNTs with narrow diameter range.
Org. Biomol. Chem., 2012,10, 5830-5836
https://doi.org/10.1039/C2OB25233C
Efficient proline and prolinol ether mediated 3-component synthesis of 3- and 3,4-substituted chromenone derivatives
A highly efficient one-pot synthesis of valuable 3,4-substituted chromenone derivatives by the reaction of 1,3-diketones with aldehydes in the presence of L-proline was developed. Chiral 3-substituted chromenones are obtained with high enantioselectivities when a chiral diarylprolinol TMS-ether is applied in the reaction.
Org. Biomol. Chem., 2012,10, 6201-6210
https://doi.org/10.1039/C2OB25443C
[2]Pseudorotaxanes , [2]rotaxanes and metal–organic rotaxane frameworks containing tetra-substituted dibenzo[24]crown-8 wheels
[2]Pseudorotaxanes, [2]rotaxanes and metal–organic rotaxane framework materials are prepared that utilise symmetrical DB24C8 analogues containing four CH2OR (R = CH2CH2CH3, CH2(C6H5), C6H5 and C6H4(4-COOEt)) substituents on the 4 and 5 positions of the aromatic rings.
Org. Biomol. Chem., 2012,10, 6094-6104
https://doi.org/10.1039/C2OB25200G
Steric desolvation enhances the effective molarities of intramolecular H-bonding interactions
Effective molarities for intramolecular phosphonate diester-phenol H-bonds vary with solvent indicating that changes in the solvation shell can make a significant contribution to the stability of a supramolecular complex.
Org. Biomol. Chem., 2012,10, 6022-6031
https://doi.org/10.1039/C2OB25372K
Synthesis of selective inhibitors against V. cholerae sialidase and human cytosolic sialidase NEU2
Two inhibitors with selectivity against V. cholerae sialidase and human cytosolic sialidase NEU2, respectively, were identified.
Org. Biomol. Chem., 2012,10, 6112-6120
https://doi.org/10.1039/C2OB25335F
The role of cyclobutenes in gold(I)-catalysed skeletal rearrangement of 1,6-enynes
A bicyclo[3.2.0]hept-5-ene formed in good yield in a gold(I)-catalysed reaction, has been structurally characterised.
Org. Biomol. Chem., 2012,10, 6105-6111
https://doi.org/10.1039/C2OB25419K
Dipicolylamine as a unique structural switching element for helical peptides
A simple method for on-resin synthesis of dipicolylamine (Dpa)-containing peptides was developed, which enables the design of a unique metal-responsive peptide.
Org. Biomol. Chem., 2012,10, 6062-6068
https://doi.org/10.1039/C2OB07118E
Desymmetrizing reductive aldol cyclizations of enethioate derivatives of 1,3-diones catalyzed by a chiral copper hydride
Enethioate derivatives of prochiral 1,3-diones underwent desymmetrizing catalytic reductive aldol cyclizations to furnish β-hydroxythioesters with >98 : 2 dr, up to 94% yield and 98% ee.
Org. Biomol. Chem., 2012,10, 5971-5978
https://doi.org/10.1039/C2OB25206F
Porphyrin dyads linked by a rotatable 3,3′-biphenyl scaffold: a new binding motif for small ditopic molecules
The complexation behaviour of a new bis-porphyrin bearing a rotatable linker with diaza-ligands has been studied. Featuring a semi-flexible biphenyl linkage, these bis-porphyrin systems are capable of reversible binding to small ditopic molecules, opening up the possibility of developing a new generation of chemoswitchable systems.
Org. Biomol. Chem., 2012,10, 6045-6053
https://doi.org/10.1039/C2OB25147G
Synthesis of a 3-deoxy-D-manno-octulosonic acid (KDO) building block from D-glucose via fermentation
A 3-deoxy-D-manno-octulosonic acid (KDO) building block was made starting from glucose through pathway engineering of Escherichia coli and subsequent chemical modifications to provide an alternative method to produce KDO, usually found in plant and bacterial oligosaccharides.
Org. Biomol. Chem., 2012,10, 5856-5860
https://doi.org/10.1039/C2OB25168J
The stereocontrolled total synthesis of spirastrellolide A methyl ester. Fragment coupling studies and completion of the synthesis
The first total synthesis of (+)-spirastrellolide A methyl ester was achieved based on the sequential coupling of four fragments and a remarkably high yielding macrolactonisation. A series of simplified analogues of spirastrellolide incorporating the C26–C47 region were also prepared by π-allyl Stille coupling reactions.
Org. Biomol. Chem., 2012,10, 5873-5886
https://doi.org/10.1039/C2OB25101A
The stereocontrolled total synthesis of spirastrellolide A methyl ester. Expedient construction of the key fragments
A modular strategy for the synthesis of the antimitotic marine macrolide spirastrellolide A methyl ester was adopted based on the envisaged sequential coupling of a series of four suitably functionalised fragments.
Org. Biomol. Chem., 2012,10, 5861-5872
https://doi.org/10.1039/C2OB25100K
Amphiphilic dynamic NDI and PDI probes: imaging microdomains in giant unilamellar vesicles
Dynamic amphiphiles with fluorescent naphthalenediimide tails can be used to label membrane microdomains and activate DNA as transporters in lipid bilayers.
Org. Biomol. Chem., 2012,10, 6087-6093
https://doi.org/10.1039/C2OB25119A
Synthesis and evaluation of new polyenic compounds as potential PPARs modulators
In order to identify new leads for the treatment of type 2 diabetes, polyenic molecules A and B derived from nipecotic acid and dienol derivatives C have been prepared and their effect on PPARs transcriptional activity evaluated and compared to that of rosiglitazone, WY14,643 and GW501516.
Org. Biomol. Chem., 2012,10, 6169-6185
https://doi.org/10.1039/C2OB25593F
Substituent effects on axle binding in amide pseudorotaxanes : comparison of NMR titration and ITC data with DFT calculations
Guest discrimination: NMR titration and ITC experiments were used to examine the binding behavior of differently disubstituted diamide guests to a tetralactam macrocycle.
Org. Biomol. Chem., 2012,10, 5954-5964
https://doi.org/10.1039/C2OB25196E
Multimodal fluorescence modulation using molecular photoswitches and upconverting nanoparticles
Different wavelengths of light can be used to selectively quench the emission from upconverting nanoparticles depending on the isomeric state of photoswitches decorated onto their surfaces.
Org. Biomol. Chem., 2012,10, 6159-6168
https://doi.org/10.1039/C2OB25368B
Combined experimental and theoretical studies on the photophysical properties of cycloparaphenylenes
Absorption and fluorescence in solution/solid states. High fluorescence quantum yields. Assignment of UV-vis absorption. Explanation of unique HOMO–LUMO behaviour.
Org. Biomol. Chem., 2012,10, 5979-5984
https://doi.org/10.1039/C2OB25199J
Peptides that anneal to natural collagen in vitro and ex vivo
Collagen mimetic peptides bind tightly to mammalian collagen in vitro and ex vivo, providing a new modality for wound care.
Org. Biomol. Chem., 2012,10, 5892-5897
https://doi.org/10.1039/C2OB25190F
On the origins of diastereoselectivity in the conjugate additions of the antipodes of lithium N-benzyl-(N-α-methylbenzyl)amide to enantiopure cis- and trans-dioxolane containing α,β-unsaturated esters
Classical doubly diastereoselective “matching” and “mismatching” effects are not observed upon conjugate addition of the antipodes of lithium N-benzyl-(N-α-methylbenzyl)amide to tert-butyl (E)-4,5-O-isopropylidene-4,5-dihydroxyhex-2-enoates.
Org. Biomol. Chem., 2012,10, 6186-6200
https://doi.org/10.1039/C2OB25099C
Structure, stereochemistry and synthesis of enantiopure cyclohexenone cis-diol bacterial metabolites derived from phenols
Biotransformation of 3- and 2,5-substituted phenols yielded enantiopure cyclohexenone cis-diols; ECD spectroscopy, X-ray crystallography and stereochemical correlation was used to establish absolute configurations.
Org. Biomol. Chem., 2012,10, 6217-6229
https://doi.org/10.1039/C2OB25079A
Construction of multi-component supramolecular architectures of bile acids and cinchona alkaloids through helical-pitch-synchronized crystallization
Multi-component organic crystals containing different kinds of helical motifs were constructed based on bile acids and cinchona alkaloids.
Org. Biomol. Chem., 2012,10, 5985-5992
https://doi.org/10.1039/C2OB25072A
Remote stereocontrol in reactions between 4- and 5-alkoxyalk-2-enylstannanes and 1-alkoxycarbonylimines and analogues: stereoselective approaches to novel α-amino acids
Reactions of the allyltin trichlorides generated from (4S)-4-benzyloxypent-2-enyl(tributyl)stannane and analogous stannanes with imines prepared from glyoxalates proceed with useful levels of 1,5-stereocontrol; modest 1,6-stereocontrol was observed using 5-hydroxy- and 5-methoxy-hex-2-enylstannanes.
Org. Biomol. Chem., 2012,10, 6130-6158
https://doi.org/10.1039/C2OB25097G
Combined coinage metal catalysis in natural product synthesis: total synthesis of (+)-varitriol and seven analogs
The combined use of the coinage metals copper and gold allows an efficient stereoselective synthesis of (+)-varitriol and various analogs.
Org. Biomol. Chem., 2012,10, 5965-5970
https://doi.org/10.1039/C2OB25069A
Platinum catalyzed 7-endo cyclization of internal alkynyl amides and its application to synthesis of the caprazamycin core
Considering the synthesis of the caprazamycin core, the scope and limitations of platinum catalyzed 7-endo cyclization of internal alkynyl amides were disclosed.
Org. Biomol. Chem., 2012,10, 6074-6086
https://doi.org/10.1039/C2OB25111F
Probing riboswitch–ligand interactions using thiamine pyrophosphate analogues
The binding of thiamine pyrophosphate (TPP) to the thiM riboswitch has been systematically explored by testing a range of TPP analogues in which the aminopyrimidine ring, the central thiazolium ring, and the pyrophosphate tail are each replaced in turn by similar structures.
Org. Biomol. Chem., 2012,10, 5924-5931
https://doi.org/10.1039/C2OB07116A
Design, synthesis and biological evaluation of non-natural modulators of quorum sensing in Pseudomonas aeruginosa
Novel potent antagonists of quorum sensing in Pseudomonas aeruginosa are reported, which strongly inhibit the production of virulence factors.
Org. Biomol. Chem., 2012,10, 6032-6044
https://doi.org/10.1039/C2OB25198A
Synthetic studies towards the mulberry Diels–Alder adducts: H-bond accelerated cycloadditions of chalcones
The methyl ether derivatives of a number of mulberry Diels–Alder adducts have been synthesized by a thermal [4 + 2]-cycloaddition reaction between a chalcone and dehydroprenyl diene. A H-bonded ortho OH substituent on the chalcone was found to be essential for Diels–Alder reactivity and the experimental results were supported by density functional theory calculations.
Org. Biomol. Chem., 2012,10, 6010-6021
https://doi.org/10.1039/C2OB25115A
Solvent and substituent effects on aggregation constants of perylene bisimide π-stacks – a linear free energy relationship analysis
In this article we have intensively addressed the question how solvents effect the aggregation strength of perylene bisimides.
Org. Biomol. Chem., 2012,10, 5845-5855
https://doi.org/10.1039/C2OB07131B
Enantioselective synthesis of 2,5-dihydrobenzo[b]azepine derivatives via iridium-catalyzed asymmetric allylic amination with 2-allylanilines and ring-closing-metathesis reaction
Iridium-catalyzed asymmetric allylic amination of allylic carbonates with 2-allylanilines and ring-closing-metathesis reaction provided highly enantioenriched 2,5-dihydrobenzo[b]azepine derivatives.
Org. Biomol. Chem., 2012,10, 5932-5939
https://doi.org/10.1039/C2OB00036A
α-N-Linked glycopeptides : conformational analysis and bioactivity as lectin ligands
NMR and modelling give new insights on the molecular recognition of unnatural α-Gal-N-linked glycopeptides by lectins.
Org. Biomol. Chem., 2012,10, 5916-5923
https://doi.org/10.1039/C2OB07135E
Chemoselective cyclization of unprotected linear peptides by α-ketoacid–hydroxylamine amide-ligation
Peptides with an N-terminal nitrone and a C-terminal α-ketoacid undergo chemoselective cyclizations without reagents and in the presence of unprotected side chains. The precursors are prepared by Fmoc-SPPS.
Org. Biomol. Chem., 2012,10, 5837-5844
https://doi.org/10.1039/C2OB25129A
Double stranded polymeric ladderphanes with 16-π-electron antiaromatic metallocycle linkers
Three double stranded polymeric ladderphanes with 16-π-electron antiaromatic metallocycle linkers are synthesised by ring opening metathesis polymerisation of the corresponding bisnorbornene monomers.
Org. Biomol. Chem., 2012,10, 5948-5953
https://doi.org/10.1039/C2OB25114K
Enantioselective synthesis of C-linked spiroacetal-triazoles as privileged natural product-like scaffolds
The union of the biologically privileged 6,6-spiroacetal scaffold with azides by the regioselective Copper-Catalysed Azide–Alkyne Cycloaddition (CuAAC) affords novel C-linked spiroacetal-triazoles. The anomeric C-linkage is anticipated to provide increased stability towards hydrolytic cleavage.
Org. Biomol. Chem., 2012,10, 5993-6002
https://doi.org/10.1039/C2OB06802H
Benzimidazole -based anion receptors: tautomeric switching and selectivity
Tautomeric switching is observed in a series of benzimidazole-based anion receptors upon addition of basic anions.
Org. Biomol. Chem., 2012,10, 5909-5915
https://doi.org/10.1039/C1OB06800H