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Rewriting the biochemistry textbooks
22 August 2008
Calculations validate alternative to a much-published enzyme mechanism

Revising the route to a stealthy siderophore
19 August 2008
Surprising result reveals details of potential enzyme target in the fight against anthrax
Chemical Communications reaches over 5 for its 2007 Impact Factor!
19 June 2008
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Contents list for Chemical Communications, issue 34, 2008
Front cover
Chem. Commun., 2008, 3941
DOI: 10.1039/b813534g

Inside front cover
Chem. Commun., 2008, 3942
DOI: 10.1039/b813536n
Contents and Chemical Technology
Chem. Commun., 2008, 3943
DOI: 10.1039/b813538j
Feature Article
Chemical communication by behaviour-guiding olfactory signals
L. Gunnar W. Bergström,
Chem. Commun., 2008, 3959
DOI: 10.1039/b712681f
Enhanced HTML article available

All living organisms have chemical signals to guide their behaviours. They are linked to all vital functions such as mating, nesting, feeding, alarm/defence and pollination. These phenomena are being studied in the new interdisciplinary area of Chemical Ecology. Here, examples are presented from insects and from flowering plants.
Communications
The foundation of a light driven molecular muscle based on stilbene and
-cyclodextrin
Ryan E. Dawson, Stephen F. Lincoln and Christopher J. Easton,
Chem. Commun., 2008, 3980
DOI: 10.1039/b809014a
Enhanced HTML article available

Flexing muscle: the rotaxane pictured serves as the basis of a light driven molecular muscle, where reversible photoisomerisation of the stilbene units causes the cyclodextrins to move on and off the stilbene units, extending and contracting the distance between the blocking groups.
An unprecedented, figure-of-eight, dinuclear iridium(I) dicarbene and new iridium(III)
pincer
complexes
Matthieu Raynal, Catherine S. J. Cazin, Christophe Vallée, Hélène Olivier-Bourbigou and Pierre Braunstein,
Chem. Commun., 2008, 3983
DOI: 10.1039/b808806c

Depending on the spacer in the bis(imidazolium) precursors, the unusual dinuclear Ir(I) complex 2 bridged by two N-heterocyclic biscarbene ligands and forming a 20-membered, figure-of-eight dimetallacycle, or new CNHCCCNHC Ir(III) pincer complexes have been obtained from [Ir(
-Cl)(cod)]2.
Fluorescent or not? Size-dependent fluorescence switching for polymer-stabilized gold clusters in the 1.1–1.7 nm size range
Nicolas Schaeffer, Bien Tan, Calum Dickinson, Matthew J. Rosseinsky, Anna Laromaine, David W. McComb, Molly M. Stevens, Yiqian Wang, Laure Petit, Catherine Barentin, David G. Spiller, Andrew I. Cooper and Raphaël Lévy,
Chem. Commun., 2008, 3986
DOI: 10.1039/b809876j

The synthesis of water-soluble polymer-stabilized gold nanoparticles is described; size-dependent visible fluorescence is observed, the size and fluorescence of the particles being controlled by the polymer-to-gold ratio.
Asymmetric intermolecular Stetter reactions catalyzed by a novel triazolium derived N-heterocyclic carbene
Dieter Enders, Jianwei Han and Alexander Henseler,
Chem. Commun., 2008, 3989
DOI: 10.1039/b809913h

The asymmetric intermolecular Stetter reaction is catalyzed by a novel triazolium salt derived N-heterocyclic carbene. The corresponding 1,4-diketones could be obtained in good yields and excellent enantiomeric excesses, after one recrystallization.
Highly diastereoselective self-assembly of chiral tris(m-ureidobenzyl)amino capsules
Mateo Alajarín, Aurelia Pastor, Raúl-Angel Orenes, Andres E. Goeta and Jonathan W. Steed,
Chem. Commun., 2008, 3992
DOI: 10.1039/b809835b

Chiral tris(m-ureidobenzyl)amines form dimeric capsules. In solution, the self-assembly process is highly diastereoselective. Moreover, the formation of the corresponding capsules in the solid state is also a completely regioselective event.
A metal–organic framework containing discrete single-walled nanotubes based on curved trinuclear [Cu3(
3-O)(
-OH)(triazolate)2]+ building blocks
Xiao-Chun Huang, Wei Luo, Yu-Feng Shen, Xin-Jian Lin and Dan Li,
Chem. Commun., 2008, 3995
DOI: 10.1039/b808240e

A novel three-dimensional nanotubular coordination polymer is assembled from cupric ions and a simple triazolate ligand, containing discrete single-walled nanotubes presumably generated from planar sheets just like carbon nanotubes.
Comment on
aggregation-induced phosphorescent emission (AIPE) of iridium(III) complexes
: origin of the enhanced phosphorescence
Youngmin You, Hyun Sue Huh, Kil Suk Kim, Soon W. Lee, Dongho Kim and Soo Young Park,
Chem. Commun., 2008, 3998
DOI: 10.1039/b806541a

An investigation of phosphorescent Ir(III) complexes attests that the most probable explanation for the reported
aggregation-induced phosphorescent emission
is restricted intramolecular motion.
Bioactive molecular sheets from self-assembly of polymerizable peptides
Kyung-Soo Moon, Eunji Lee, Yong-beom Lim and Myongsoo Lee,
Chem. Commun., 2008, 4001
DOI: 10.1039/b806559d
Enhanced HTML article available

We have demonstrated that polymerizable peptides self-assemble into a unique sheet-like 2D structure in bulk solution that can be covalently fixed to produce 2D molecular objects which were shown to be efficient at delivering cargos into living cells and are nearly nontoxic in contrast to non-polymerized nanostructures.
Self-assembly and multicolor emission of core/shell structured CaWO4:Na+/Ln3+ spheres
Yiguo Su, Liping Li and Guangshe Li,
Chem. Commun., 2008, 4004
DOI: 10.1039/b810648g
Enhanced HTML article available

A novel core/shell CaWO4 microsphere co-doped with Na+ and Ln3+ (Ln = Dy, Tb, Sm, Eu) was prepared and showed a unique multicolor emission in the visible region when excited by single-wavelength light.
Palladium(II)-gated ion channels
Craig P. Wilson and Simon J. Webb,
Chem. Commun., 2008, 4007
DOI: 10.1039/b809087d
Enhanced HTML article available

A cholic acid-derived channel that can be gated by palladium(II) has been developed. Addition of palladium(II) assembled the channel and allowed Na+ or K+ to cross the bilayer; subsequent addition of hexathia-18-crown-6 (18S6) extracted the palladium(II) and stopped ion flow.
Redesigned tetrads with altered hydrogen bonding patterns enable programming of quadruplex topologies
Armin Benz and Jörg S. Hartig,
Chem. Commun., 2008, 4010
DOI: 10.1039/b805227a
Enhanced HTML article available

Incorporation of xanthosine and 8-oxoguanosine into G-rich oligonucleotides makes it possible to selectively program the topology of quadruplex structures. The guanosine derivatives assemble into tetrads, restricting the number of possible conformations of the four-stranded nucleic acid structures.
Silver carbonate nanoparticles stabilised over alumina nanoneedles exhibiting potent antibacterial properties
Joanna J. Buckley, Pratibha L. Gai, Adam F. Lee, Luca Olivi and Karen Wilson,
Chem. Commun., 2008, 4013
DOI: 10.1039/b809086f
Enhanced HTML article available

Simple wet chemical methodologies allow the preparation of Ag2CO3 nanoparticles dispersed over
-alumina nanoneedles that exhibit potent antimicrobial properties.
Fabrication of monodisperse silica–polymer core–shell nanoparticles with excellent antimicrobial efficacy
Jyongsik Jang and Yura Kim,
Chem. Commun., 2008, 4016
DOI: 10.1039/b809137d

Monodisperse nanoparticles with antimicrobial polymer shells were fabricated using a seeded copolymerization; they exhibited excellent antibacterial activities.
Two highly-connected, chiral, porous coordination polymers featuring novel heptanuclear metal carboxylate clusters
Lei Hou, Jie-Peng Zhang, Xiao-Ming Chen and Seik Weng Ng,
Chem. Commun., 2008, 4019
DOI: 10.1039/b809069f

Two unprecedented (3,12)-connected, chiral, porous frameworks are constructed by benzene-1,3,5-tribenzoate and two types of heptanuclear clusters, featuring 3D pore structures, selective sorption and solvothermal resistance properties.
Ordered mesoporous Co3O4 as highly active catalyst for low temperature CO-oxidation
Harun Tüysüz, Massimiliano Comotti and Ferdi Schüth,
Chem. Commun., 2008, 4022
DOI: 10.1039/b808815b

Cubic ordered mesoporous Co3O4, prepared via the nanocasting pathway using KIT-6 as hard template, was found to be an excellent catalyst for low temperature CO oxidation, with the activity clearly depending on surface area and pore systems of the catalysts.
Cyclooctatrienes from pyran-2-ones via a tandem [4 + 4]-photocycloaddition/decarboxylation process
Lei Li, Charles E. Chase and F. G. West,
Chem. Commun., 2008, 4025
DOI: 10.1039/b806871b

Irradiation of pyran-2-ones connected to furans by a three-carbon tether furnishes [4 + 4]-photocycloadducts as a mixture of endo and exo diastereomers, whose thermal decarboxylation then provides ether-bridged cyclooctatrienes in generally moderate to good yields.
Remote induction of asymmetry in [13]-macro-dilactone topology by a single stereogenic center
W. Sean Fyvie and Mark W. Peczuh,
Chem. Commun., 2008, 4028
DOI: 10.1039/b807562j

Analysis of a series of unsaturated [13]-macro-dilactones showed that the configuration of a single carbon dictates the planar chirality of a macrocycle backbone and in turn remotely switches the facial display of an embedded alkene unit.
Substituent effects on the aromatic edge-to-face interaction
Felix Raoul Fischer, W. Bernd Schweizer and François Diederich,
Chem. Commun., 2008, 4031
DOI: 10.1039/b809058k

The fine tuning of substituent effects on the folding equilibrium of molecular torsion balances is rationalised on the basis of changes in the incremental contributions of dispersion, electrostatic and exchange repulsion forces to the overall interaction energy.
Petrobactin biosynthesis: AsbB catalyzes condensation of spermidine with N8-citryl-spermidine and its N1-(3,4-dihydroxybenzoyl) derivative
Daniel Oves-Costales, Nadia Kadi, Mark J. Fogg, Lijiang Song, Keith S. Wilson and Gregory L. Challis,
Chem. Commun., 2008, 4034
DOI: 10.1039/b809353a
Enhanced HTML article available

AsbB is shown to catalyse the regioselective ATP-dependent condensation of spermidine with N8-citryl-spermidine or its N1-(3,4-dihydroxybenzoyl) derivative in the assembly of petrobactin, leading to a revision of the proposed biosynthetic pathway for this anthrax stealth siderophore.
Synthesis and properties of DNA containing a spore photoproduct analog
Eva Bürckstümmer and Thomas Carell,
Chem. Commun., 2008, 4037
DOI: 10.1039/b810008j
Enhanced HTML article available

The spore photoproduct is a unique photolesion, formed in spores upon irradiation with UV light. To investigate the properties of spore photoproduct containing DNA the authors have synthesized 5S and 5R lesion analogs and incorporated them into DNA.
Chiral N-heterocyclic carbene ligands for asymmetric catalytic oxindole synthesis
Yi-Xia Jia, J. Mikael Hillgren, Emma L. Watson, Stephen P. Marsden and E. Peter Kündig,
Chem. Commun., 2008, 4040
DOI: 10.1039/b810858g
Enhanced HTML article available

The Pd-catalysed asymmetric intramolecular
-arylation of amide enolates containing heteroatom substituents gives chiral 3-alkoxy or 3-aminooxindoles in high yield and enantiomeric purity. Key to this success is a new chiral N-heterocyclic carbene ligand.
Synthesis and reactivity of bis-pentamethylcyclopentadienyl diiododialane (Cp*AlI)2: an aluminium(II) precursor to (Cp*Al)4
Stefan G. Minasian and John Arnold,
Chem. Commun., 2008, 4043
DOI: 10.1039/b806804f

Reduction of Cp*AlI2(OEt2) in toluene gave bis-pentamethylcyclopentadienyl diiododialane (Cp*AlI)2 ( 1), which functions as an intermediate in the synthesis of (Cp*Al)4 and undergoes oxidative cleavage of the Al–Al bond with an aryl azide.
Application of CuOx–CeO2 catalysts as selective sensor substrates for detection of CO in H2 fuel
Christopher S. Polster and Chelsey D. Baertsch,
Chem. Commun., 2008, 4046
DOI: 10.1039/b807241h

The applicability and mechanism of CuOx–CeO2 as a catalytic microsensor substrate enabling 100% selective detection of low concentration CO in gas mixtures with H2 is described.
Transport of metal salts by zwitterionic ligands; simple but highly efficient salicylaldoxime extractants
Ross S. Forgan, James E. Davidson, Stuart G. Galbraith, David K. Henderson, Simon Parsons, Peter A. Tasker and Fraser J. White,
Chem. Commun., 2008, 4049
DOI: 10.1039/b808696f

Attaching dialkylaminomethyl arms to commercial phenolic oxime copper extractants yields reagents which transport base metal salts very efficiently.
Direct, facile synthesis of N-acyl-
-amino amides from
-keto esters and ammonia
Rukundo Ntaganda, Tamara Milovic, Jorge Tiburcio and Avinash N. Thadani,
Chem. Commun., 2008, 4052
DOI: 10.1039/b808302a
Enhanced HTML article available

A variety of N-acyl-
-amino amides are synthesized in high yields in one step by simply heating the corresponding
-keto esters in methanolic ammonia.
Gas-phase synthesis of the rare-gas carbene cation ArCH2+ using doubly ionised bromomethane as a superelectrophilic reagent
Daniela Ascenzi, Paolo Tosi, Jana Roithová and Detlef Schröder,
Chem. Commun., 2008, 4055
DOI: 10.1039/b811115d

The bimolecular reaction of doubly ionized methyl bromide with argon affords the argon–carbene cation ArCH2+, which is an example of a new class of organo rare-gas compounds.
The promoting effect of a dicyanamide based ionic liquid in the selective hydrogenation of citral
Jürgen Arras, Martin Steffan, Yalda Shayeghi and Peter Claus,
Chem. Commun., 2008, 4058
DOI: 10.1039/b810291k

Conventional supported heterogeneous palladium catalysts in combination with a dicyanamide based ionic liquid are highly active with excellent selectivity and yield in enabling the one-pot synthesis of citronellal through citral hydrogenation.
Structures of two haptotropic isomers generated by the sliding of 1,3,5-triene ligands on a Pd–Pd–Pd chain
Tetsuro Murahashi, Yukari Mino, Koji Chiyoda, Sensuke Ogoshi and Hideo Kurosawa,
Chem. Commun., 2008, 4061
DOI: 10.1039/b806824k

The structures of haptotropic isomers generated by the sliding of 1,3,5-triene ligands in a linear Pd3 sandwich complex were structurally characterized by X-ray crystallographic analyses.
Synthesis and unprecedented coordination behaviour of a novel 1,2,3-triphosphaferrocene complex
Shining Deng, Christoph Schwarzmaier, Christiane Eichhorn, Otto Scherer, Gotthelf Wolmershäuser, Manfred Zabel and Manfred Scheer,
Chem. Commun., 2008, 4064
DOI: 10.1039/b807658h

A novel 1,2,3-triphosphaferrocene has been synthesised. It reacts with CuBr to give a 2D polymer, revealing an unprecedented
-stacking of the triphospholyl moieties.
A meso-meso directly linked octameric porphyrin square
Naoki Aratani and Atsuhiro Osuka,
Chem. Commun., 2008, 4067
DOI: 10.1039/b807351a

A meso-meso directly linked cyclic porphyrin square was synthesized via stepwise Suzuki–Miyaura cross coupling reactions. This cyclic architecture has a designed large
nano-space
(ca. 1.6 × 1.6 × 0.7 nm3) as the inside cavity, and can capture a guest molecule.
Luminescent Au(III) organometallic complex of N-confused tetraphenylporphyrin
Motoki Toganoh, Teppei Niino and Hiroyuki Furuta,
Chem. Commun., 2008, 4070
DOI: 10.1039/b807922f

An organometallic Au(III) complex of N-confused tetraphenylporphyrin has been synthesized; unique emission properties are observed in solution at ambient temperature.
Unexpected bond activation of small organic molecules on a metal oxide—butane/CaO(100)
Evgueni B. Kadossov and U. Burghaus,
Chem. Commun., 2008, 4073
DOI: 10.1039/b804472d

An example of bond activation of small alkanes on a metal oxide at low surface temperatures is presented. The reactivity is affected by internal degrees of freedom.
Target-driven selection in a dynamic nitrone library
Simon M. Turega, Christiane Lorenz, Jan W. Sadownik and Douglas Philp,
Chem. Commun., 2008, 4076
DOI: 10.1039/b805945d
Enhanced HTML article available

A receptor for a glutaric acid derivative is selected from a pool of four exchanging nitrones.
Back cover
Chem. Commun., 2008, 4079
DOI: 10.1039/b813540c
