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Graphical Abstract Angew. Chem. Int. Ed. 442006

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The following Communications have been judged by at least two referees to be ?very
important papers? and will be published online at soon:
A. Corma,* M. Renz*
A General Method for the Preparation of Ethers Using
Water-Resistant Solid Lewis Acids
R. Martinez, R. Chevalier, S. Darses,* J.-P. Genet*
A Versatile Ruthenium Catalyst for C?C Bond Formation through
C?H Bond Activation
K. Banert,* Y.-H. Joo, T. Rffer, B. Walfort, H. Lang
The Exciting Chemistry of Tetraazidomethane
H. Nuss, M. Jansen*
Cs5([12]crown-4)2(O3)5 : The First Supramolecular Ozonide
Compound Containing 1Ц{Cs8(O3)10}2 Rods
B. V. Popp, J. E. Wendlandt, C. R. Landis,* S. S. Stahl*
Reaction of Molecular Oxygen with an NHC-Coordinated Pd0
Complex: Computational Insights and Experimental
F. Camerel, R. Ziessel,* B. Donnio, C. Bourgogne, D. Guillon,
M. Schmutz, C. Iacovita, J.-P. Bucher
Formation of Gels and Liquid Crystals Induced by Pt и и и Pt
Interactions in Luminescent s-Alkynyl Platinum(II) Terpyridine
E. Delamarche honored
Biophysical Chemistry:
Awards to T. Fiebig and H.-A. Wagenknecht
Organic Photovoltaics
Sam-Shajing Sun, Niyazi Serdar Sariciftci
reviewed by N. Robertson
Chemical Micro Process Engineering
Volker Hessel, Holger L-we, Andreas
M.ller, Gunther Kolb
reviewed by C. de Bellefon
Too much fiber? Protein fibers play an
important role in cellular processes, but
are also involved in protein-folding diseases, such as Alzheimer?s disease.
Modern screening and validation models
allow the investigation of the aggregation
and deaggregation kinetics of protein
fibers (see scheme). These studies can
serve as a starting point for the development of new therapeutic strategies.
Taming of the flu: Shikimic and quinic
acids are the established starting materials for Tamiflu, a viral neuraminidase
inhibitor that is considered by many as the
first-line treatment against a possible
H5N1 (bird flu) pandemic. Several synth-
eses have been described recently that
circumvent the use of these natural
products. These, or related approaches,
may provide an alternative practical
approach to this important drug.
Alzheimer?s Disease
W. H. Binder,* O. W. Smrzka 7324 ? 7328
Self-Assembly of Fibers and Fibrils
Antiviral Agents
V. Farina,* J. D. Brown*
7330 ? 7334
Tamiflu: The Supply Problem
2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Angew. Chem. Int. Ed. 2006, 45, 7308 ? 7318
Reactions that go with the flow: Many
applications in chemical research require
multiple reactions to be performed in
parallel and in series. Microfluidic droplets can be used as chemical microreactors for performing many reactions on
small scale (see picture). New techniques
in droplet-based microfluidics and their
applications (e.g., for analysis of complex
biological processes or optimization of
reaction conditions) are discussed.
Droplet-Based Microfluidics
H. Song, D. L. Chen,
R. F. Ismagilov*
7336 ? 7356
Reactions in Droplets in Microfluidic
Hydrogen Storage
First-class accommodation: A series of
coordination frameworks with different
pore sizes (see structure of one; Cu blue,
C gray, H white, O red) are prepared from
CuII ions and carboxylate ligands of various lengths. Comparison of their sorption properties reveals that smaller pores
allow higher densities of adsorbed H2,
whereas larger pores allow higher maximum H2 storage capacities.
X. Lin, J. Jia, X. B. Zhao, K. M. Thomas,
A. J. Blake, G. S. Walker,
N. R. Champness,* P. Hubberstey,*
M. Schr-der*
7358 ? 7364
High H2 Adsorption by CoordinationFramework Materials
Playing tag: Noncanonical amino acid
tagging enables the selective fluorescent
visualization of newly synthesized proteins in mammalian cells (see the picture). Susceptibility to tagging is determined by the spatial and temporal character of the protein synthesis, thus providing a complement to methods which
identify relevant members of the proteome.
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Angew. Chem. Int. Ed. 2006, 45, 7308 ? 7318
Meacham Ave., Elmont, NY 11003. Periodicals
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NJ 07030. Annual subscription price for institutions: US$ 5685/5168 (valid for print and
Fluorescent Probes
K. E. Beatty, J. C. Liu, F. Xie,
D. C. Dieterich, E. M. Schuman, Q. Wang,
D. A. Tirrell*
7364 ? 7367
Fluorescence Visualization of Newly
Synthesized Proteins in Mammalian Cells
electronic / print or electronic delivery); for
individuals who are personal members of a
national chemical society prices are available
on request. Postage and handling charges
included. All prices are subject to local VAT/
sales tax.
2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
A sunny outlook: As the first fully heterocyclic circulene, sulflower opens the way
to an unprecedented class of compounds
that are both organic and inorganic. Sulflower is an oligothiophene as well as a
new form of carbon sulfide that resembles
a flower (see picture) and was synthesized
in a short and effective approach.
Sulfur Heterocycles
K. Y. Chernichenko, V. V. Sumerin,
R. V. Shpanchenko, E. S. Balenkova,
V. G. Nenajdenko*
7367 ? 7370
?Sulflower?: A New Form of Carbon
A new approach to stabilization of ZnO
nanocrystals by ionic-liquid components,
which endow the nanocrystals with high
thermal stability and good fluidity, is
demonstrated. The ionic-liquid/ZnO
composites exhibit tunable photoluminescence (see picture) with a high quantum yield.
ZnO Nanocrystals
Unbalanced surface stresses, induced in
stereocomplex crystals formed by blends
of two enantiomeric polylactide diblock
copolymers by the presence of immiscible
blocks of different lengths, result in
lamella curving and formation of onionlike multilamellar structures (see picture
for schematic structure and a TEM
Lamellar Materials
D. P. Liu, G. D. Li, Y. Su,
J. S. Chen*
Highly Luminescent ZnO Nanocrystals
Stabilized by Ionic-Liquid Components
L. Sun, L. Zhu,* L. Rong,
B. S. Hsiao
7373 ? 7376
Tailor-Made Onionlike Stereocomplex
Crystals in Incompatible, Enantiomeric,
Polylactide-Containing Block Copolymer
Successive oxidation processes in a heterobimetallic iron?ruthenium complex
(see picture) ?switch? the optical transitions at long wavelengths, and these
linear electrochromic effects are accompanied by changes in the nonlinear optical
properties of the complex.
Angew. Chem. Int. Ed. 2006, 45, 7308 ? 7318
7370 ? 7373
Nonlinear Optics
M. Samoc,* N. Gauthier, M. P. Cifuentes,
F. Paul,* C. Lapinte,
M. G. Humphrey*
7376 ? 7379
Electrochemical Switching of the Cubic
Nonlinear Optical Properties of an
Aryldiethynyl-Linked Heterobimetallic
Complex between Three Distinct States
2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Molecular Wheels
P. King, T. C. Stamatatos, K. A. Abboud,
G. Christou*
7379 ? 7383
Reversible Size Modification of Iron and
Gallium Molecular Wheels: A Ga10 ?Gallic
Wheel? and Large Ga18 and Fe18 Wheels
Wheelin? and dealin?: The M10 molecular
wheels [M10(OMe)20(O2CR)10] (M = Ga,
R = Me; M = Fe, R = Ph) were modified to
M18 wheels in a nontemplate synthesis
upon incorporation of a diolate ligand
(see space-filling model of [Ga18(pd)12(pdH)12(O2CMe)6(NO3)6]6+; Ga yellow,
O red, N blue, C gray; pdH2 = 1,3-propanediol). Remarkably, dissolution in MeOH
converts both M18 wheels back into the
M10 wheels.
DNA Structures
Highly sensitive: Analysis of viral DNA
(M13 phage) is possible by using a DNAbased machine that is fueled by dNTPs
and synthesizes DNAzyme reporter units.
The DNAzymes mimic peroxidase and
lead to a colorimetric or chemiluminescent readout of the analyzed DNA.
Y. Weizmann, M. K. Beissenhirtz,
Z. Cheglakov, R. Nowarski, M. Kotler,
I. Willner*
7384 ? 7388
A Virus Spotlighted by an Autonomous
DNA Machine
Conformation Analysis
V. M. SOnchez-Pedregal, K. Kubicek,
J. Meiler, I. Lyothier, I. Paterson,
T. Carlomagno*
7388 ? 7394
The Tubulin-Bound Conformation of
Discodermolide Derived by NMR Studies
in Solution Supports a Common
Pharmacophore Model for Epothilone and
Iron Imido Complexes
E. J. Klinker, T. A. Jackson, M. P. Jensen,
A. Stubna, G. JuhOsz, E. L. Bominaar,
E. M.nck,* L. Que, Jr.*
7394 ? 7397
A Tosylimido Analogue of a Nonheme
Oxoiron(IV) Complex
Bound to have similarities: Although the
overall shape of discodermolide bound to
tubulin resembles the structure of the free
ligand, the precise conformation and
orientation of the lactone ring are different. A partially overlapping pharmacophore model supported by protein-mediated interligand NOE signals (see picture)
is proposed to explain the similar (but not
fully equivalent) biological activity of discodermolide and epothilone A.
High-valent versatility: N4Py is a versatile
pentadentate ligand demonstrated to
stabilize both high-valent oxo and imido
compounds. The [FeIV(NTs)(N4Py)]2+
complex (see DFT-optimized structure)
has been characterized spectroscopically
and formulated as having an S = 1
iron(IV) center with an Fe=N bond
(1.73 R) that is longer than the Fe=O bond
of its oxo analogue (1.65 R).
2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Angew. Chem. Int. Ed. 2006, 45, 7308 ? 7318
Amino Acids
J. Wolfer, T. Bekele, C. J. Abraham,
C. Dogo-Isonagie, T. Lectka* 7398 ? 7400
Cycloaddition of o-benzoquinone imides
with chiral ketene enolates derived from
cinchona alkaloid catalysts is the basis of
a catalytic asymmetric synthesis of 1,4benzoxazinones and 1,4-benzoxazines.
The resulting cycloadducts can be deriva-
tized in situ to provide a-amino acid
products in good-to-excellent yields with
very high enantioselectivities (see
scheme; CAN = ceric ammonium nitrate,
Nu = nucleophile).
Catalytic, Asymmetric Synthesis of
1,4-Benzoxazinones: A Remarkably
Enantioselective Route to a-Amino Acid
Derivatives from o-Benzoquinone Imides
Giving it a tri: Ternary complexes formed
from a macrocyclic host (p-sulfonatocalix[4]arene), an organic guest (2,3diazabicyclo[2.2.2]oct-2-ene), and transition-metal ions (see picture) result in a
host-assisted formation of a metal?ligand
bond. The system displays a very high
selectivity as a result of triple supramolecular recognition involving Coulombic interactions, hydrophobic guest binding, and weak metal?ligand interactions.
Supramolecular Chemistry
Surface value: Scanning tunneling microscopy reveals that aryl?carbonyl assemblies
form through C HиииO interactions on a
Pt(111) surface (see picture). The strong
hydrogen bonding is activated by the
chemisorption-induced polarization of the
arene and is tunable by substitution on
the aromatic ring. These findings are
relevant to stereoselective heterogeneous
and homogeneous catalysis.
Asymmetric Catalysis
H. Bakirci, A. L. Koner, M. H. Dickman,
U. Kortz, W. M. Nau*
7400 ? 7404
Dynamically Self-Assembling
Metalloenzyme Models Based on
S. Lavoie, G. Mahieu,
P. H. McBreen*
7404 ? 7407
Chemisorption-Induced Double
Hydrogen Bonding, Self-Assembly, and
Activity-Based Proteomics
K. T. Barglow, B. F. Cravatt*
7408 ? 7411
Substrate Mimicry in an Activity-Based
Probe That Targets the Nitrilase Family of
Up and at it: A set of activity-based
proteomics probes containing a dipeptide
a-chloroacetamide scaffold that targets
the nitrilase family of enzymes is described. One member of the nitrilase
Angew. Chem. Int. Ed. 2006, 45, 7308 ? 7318
class, ureidopropionase-b, was found to
react selectively with a single probe that
mimics the enzyme?s endogenous substrate N-carbamoyl b-alanine.
2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Coordination Frameworks
Bridging two traditional but distinct
research areas?polyoxometalate
chemistry and cuprous halide clusters?
the (4,12)-connected 3D framework
(NH4)[Cu24I10L12][PMoV2MoVI10O40]3 has
been built by covalent linkage of nanoscale Keggin anions and [Cu24I10L12]14+
clusters (see picture; L is a multidentate
N-heterocyclic ligand); it exhibits remarkable photoluminescent and electrochemical properties.
X.-L. Wang, C. Qin, E.-B. Wang*
Z.-M. Su,* Y.-G. Li, L. Xu
7411 ? 7414
Self-Assembly of Nanometer-Scale
[Cu24I10L12]14+ Cages and Ball-Shaped
Keggin Clusters into a (4,12)-Connected
3D Framework with Photoluminescent
and Electrochemical Properties
DNA Structures
Behind bars: A single molecule of the
protein cytochrome c has been incarcerated within a rigid tetrahedral DNA cage
(see picture). The central cavity is estimated to be large enough to accommodate a sphere of approximately 2.6 nm in
radius, such as a 60-kDa globular protein
(Mr of cytochrome c: 12.4 kDa). The finding demonstrates the potential of DNA
containers as a new kind of drug-delivery
C. M. Erben, R. P. Goodman,
A. J. Turberfield*
7414 ? 7417
Single-Molecule Protein Encapsulation in
a Rigid DNA Cage
Sialic Acid Synthesis
Z. Hong, L. Liu, C.-C. Hsu,
C.-H. Wong*
7417 ? 7421
Three-Step Synthesis of Sialic Acids and
Flexible yet efficient: Sialic acids such as
l-N-acetylneuraminic acid (see picture)
can be synthesized in only three steps by
1) vinylation of an aldose through a
modified Petasis coupling reaction, 2) 1,3-
dipolar cycloaddition with a nitrone to
construct an isoxazolidine ring, and
3) base-catalyzed b elimination/ring
opening of the isoxazolidine to generate a
g-hydroxy-a-keto acid.
A C1 source, the carbido complex [Ru(C)(PCy3)2Cl2] (1) adds cleanly to dimethylacetylene dicarboxylate (DMAD), affording the cyclopropenylidene complex 2
(red O, green Cl, yellow P, gray C). This
product is surprising given the instability
of its trans-cyclopropylidene analogue. HX
reagents effect 1,1-addition and ring
opening, forming vinylidene complexes
such as 3 which catalyze the ring-opening
metathesis polymerization of norbornene.
Carbido Complexes
S. R. Caskey, M. H. Stewart,
M. J. A. Johnson,*
J. W. Kampf
7422 ? 7424
Carbon?Carbon Bond Formation at a
Neutral Terminal Carbido Ligand:
Generation of Cyclopropenylidene and
Vinylidene Complexes
2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Angew. Chem. Int. Ed. 2006, 45, 7308 ? 7318
Single-Molecule Magnets
To cap it off: A high-spin cyanide-bridged
Ni9W6 cluster (S = 12) shows ferromagnetic coupling between NiII (green) and
WV (purple) ions within the molecule. The
surface was modified by substituting the
solvent molecules on the surface of the
cluster with 2,2?-bipyridine to afford an airstable Ni9W6 cluster with single-molecule
J. H. Lim, J. H. Yoon, H. C. Kim,
C. S. Hong*
7424 ? 7426
Surface Modification of a Six-Capped
Body-Centered Cube Ni9W6 Cluster:
Structure and Single-Molecule
A golden tandem reaction: The
[PPh3AuCl]/AgSbF6 catalytic system promotes a tandem reaction composed of a
Friedel?Crafts-type addition of electronrich aromatic and heteroaromatic derivatives to unactivated alkenes and a carbocyclization (see scheme; Z = C(CO2Me)2,
C(SO2Ph)2, O, NTs). The reaction is
compatible with various functional groups
on the enynes and nucleophiles, and
proceeds rapidly at room temperature.
Going retro: Controlled-potential electrolysis (CPE) is employed as a synthetic tool
in the selective removal of addends from
fullerene adducts. Reductive CPE has
been extensively used in the retro-cyclopropanation of fullerenes without affecting pyrrolidine addends also present. Now
oxidative CPE for the selective removal of
pyrrolidine addends in the presence of
methano adducts is reported (see
P. Y. Toullec, E. Genin, L. Leseurre,
J.-P. Genяt,* V. Michelet*
7427 ? 7430
Room-Temperature AuI-Catalyzed C C
Bond Formation through a Tandem
Friedel?Crafts-Type Addition/
Carbocyclization Reaction
O. Lukoyanova, C. M. Cardona, M. Altable,
S. Filippone, V. MartWn Domenech,
N. MartWn,* L. Echegoyen* 7430 ? 7433
Selective Electrochemical RetroCycloaddition Reaction of
Cast in a new role: Aqueous solutions of
OsO4 and NaIO4 oxidize methane to
methanol under very mild conditions (see
scheme). The generated methanol is preserved over 5 days at 50 8C, although it is
more readily oxidized than methane in
separate experiments. Remarkably,
methanol oxidation by aqueous OsO4/
NaIO4 is inhibited by the presence of
Angew. Chem. Int. Ed. 2006, 45, 7308 ? 7318
C H Activation
Methane and Methanol Oxidation
T. Osako, E. J. Watson, A. Dehestani,
B. C. Bales, J. M. Mayer*
7433 ? 7436
Methane Oxidation by Aqueous Osmium
Tetroxide and Sodium Periodate:
Inhibition of Methanol Oxidation by
2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
J. Y Baek, T. J. Choi, H. B. Jeon,
K. S. Kim*
7436 ? 7440
A Highly Reactive and Stereoselective
b-Mannopyranosylation System:
Mannosyl 4-Pentenoate/PhSeOTf
Controlled linkage: PhSeOTf-promoted
glycosylations of a variety of acceptor
alcohols with 4,6-O-benzylidene-2,3-di-Obenzylmannopyranosyl pentenoate afford
b-mannopyranosides in high yields and
with excellent stereoselectivity (see
scheme). This method is even better than
other known methods for the mannosylation of simple reactive primary alcohols.
Tf = trifluoromethanesulfonyl,
TTBP = 2,4,6-tri-tert-butylpyrimidine.
Brushing up on films: A simple model,
based on strong ion-pairing interactions
of a dye probe (bromothymol blue, BTB)
within surface-grafted charged polyelectrolyte brushes, provides evidence that
physical forces can be easily mechano-
transducted into chemical signals (see
picture, PDMS = poly(dimethylsiloxane)).
The application of a mechanical force
results in a shift of the equilibrium for
BTB, which can be monitored by UV/Vis
Surface Chemistry
O. Azzaroni, B. Trappmann, P. van Rijn,
F. Zhou, B. Kong,
W. T. S. Huck*
7440 ? 7443
Mechanically Induced Generation of
Counterions Inside Surface-Grafted
Charged Macromolecular Films: Towards
Enhanced Mechanotransduction in
Artificial Systems
Block Copolymers
T. Azzam, A. Eisenberg*
7443 ? 7447
Control of Vesicular Morphologies
through Hydrophobic Block Length
About the size of it: A series of polystyrene-block-poly(acrylic acid) (PS-b-PAA)
block copolymers were developed in
which the length of the PAA block was
kept constant and the length of the PS
block was varied. This allowed a study of
the effect of the PAA/PS block ratio on the
vesicle sizes as well as on the wall
P-Substituted Carbenes
S. Marrot, T. Kato,* F. P. CossWo,
H. Gornitzka, A. Baceiredo* 7447 ? 7450
Cyclic Carbodiphosphorane?
Diphosphinocarbene Thermal
Unusual thermal ring contraction of fivemembered cyclic azacarbodiphosphorane
into a four-membered 1,2l5-azaphosphete
was observed (see scheme). Experimental
and computational results indicate that
2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
the ring contraction results from a
remarkable interconversion between two
different types of divalent carbon species
(dianionic and carbene): carbodiphosphorane and diphosphinocarbene.
Angew. Chem. Int. Ed. 2006, 45, 7308 ? 7318
Pin point: Accurate positioning of highly
sensitive and selective NO microsensors
by using a shear-force-dependent constant-distance mode of SECM allows
reproducible detection of stimulated NO
release from adherently growing endothelial cells. The picture shows the diffusion profile of NO after stimulation of a
cell (right) and the amperometric current
trace of a microsensor positioned over a
cell (left).
7451 ? 7454
Detection of Nitric Oxide Release from
Single Cells by Using Constant-DistanceMode Scanning Electrochemical
S. Daum, F. Erdmann, G. Fischer,
B. FXaux de Lacroix,
A. Hessamian-Alinejad, S. Houben,
W. Frank, M. Braun*
7454 ? 7458
Aryl Indanyl Ketones: Efficient Inhibitors
of the Human Peptidyl Prolyl cis/trans
Isomerase Pin1
How to get into films: Micropatterned
poly(methacrylic acid) (PMAA) brushes
are used as an ionotropic matrix for the
fabrication of microstructured calcite thin
films. The calcite films are an exact 3D
replica of the PMAA brush matrix (see
Scheme; ACC = amorphous CaCO3
Angew. Chem. Int. Ed. 2006, 45, 7308 ? 7318
S. Isik, W. Schuhmann*
Enzyme Inhibitors
A good imitation: Aryl-1-indanyl ketones
are found to be highly efficient, reversible,
cell-penetrating inhibitors of the human
peptidyl prolyl cis/trans isomerase Pin1.
Owing to their structure 1, they are
assumed to mimic the transition state 2 of
the enzymatically catalyzed rotation about
the imidic peptide bond preceding a
proline residue.
I see red, I see red, I see red: Optically
switchable compounds were synthesized
whose visible fluorescence can be quenched down to 6 % with light at 360?
400 nm and then restored with red light
from a diode laser. The molecular switch
offers potential applications in data storage and far-field microscopy with spatial
resolution far below the diffraction limit.
NO Microsensors
Biomimetic Thin Films
S. Tugulu, M. Harms, M. Fricke,
D. Volkmer,* H.-A. Klok*
7458 ? 7461
Polymer Brushes as Ionotropic Matrices
for the Directed Fabrication of
Microstructured Calcite Thin Films
Molecular Switches
M. Bossi, V. Belov, S. Polyakova,
S. W. Hell*
7462 ? 7465
Reversible Red Fluorescent Molecular
2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Intermetallic Compounds
M.-H. Whangbo,* C. Lee,
J. K-hler*
A negative disposition: Electronic-bandstructure calculations reveal that in
La2M2In (M = Pt, Cu) the transition-metal
atoms can be regarded as anions with
fully occupied nd orbitals and bonding
characters similar to that of the Ge3 ions
in La2Ge2In. The orbital sequence in
La2M2In is (n + 1)s < nd < (n + 1)p, as a
result of the low oxidation states of the
transition metals (see graph).
7465 ? 7469
Transition-Metal Anions in Solids and
Their Implications on Bonding
Supporting information available on the WWW
(see article for access details).
A video clip is available as Supporting Information
on the WWW (see article for access details).
For more information on
Chemistry?An Asian Journal see
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