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Graphical Abstract Angew. Chem. Int. Ed. 292005

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Contents
The following Communications have been judged by at least two referees to be “very
important papers” and will be published online at www.angewandte.org soon:
V. Lavallo, Y. Canac, C. Prsang, B. Donnadieu, G. Bertrand*
Stable Cyclic (Alkyl)(amino)carbenes as Rigid or Flexible, Bulky,
Electron-Rich Ligands for Transition-Metal Catalysts
X. Liang,* D. Fu, R. Liu,* Q. Zhang, T. Y. Zhang, X. Hu*
Highly Efficient NaNO2-Catalyzed Destruction of Trichlorophenol
using Molecular Oxygen
S. Aime,* D. Delli Castelli, E. Terreno
Highly Sensitive MRI-CEST Agents using Liposomes (LIPOCEST)
P. Maire, T. B.ttner, F. Breher, P. Le Floch, H. Gr.tzmacher*
Heterolytic Hydrogen Splitting with Novel Rhodium(I) Amides
H. Braunschweig,* K. Radacki, D. Rais, D. Scheschkewitz
A T-Shaped Platinum(II) Boryl Complex as the Precursor to a
Base-Stabilized Borylene of Platinum
D. Banser, M. Schnell, J.-U. Grabow,* E. J. Cocinero, A. Lesarri,
J. L. Alonso
The Internuclear Potential, Electronic Structure, and Chemical
Bond of Tellurium Selenide
Web Sites
http://molmovdb.org/
Proteins in Motion
D. Heinz,* W.-D. Schubert
4428
Nanofabrication Towards Biomedical
Applications
Challa S. S. R. Kumar, Josef Hormes,
Carola Leuschner
reviewed by E. Katz
4429
Side Reactions in Organic Synthesis
Florencio Zaragoza-D/rwald
reviewed by M. A. Sierra
4430
Rule of thumb: Deciding the fate of drug
candidates after an estimate of oral
bioavailability depends on how heavily the
selection parameters are applied. A retrospective analysis of medications on the
market has shown that lipophilicity, per-
cent polar surface area, and the number of
H-bond donors are properties that have
remained relatively constant over the
years, and are clearly the most important
physicochemical determinants.
Copper complements palladium as a
catalyst of asymmetric allylic substitutions (see scheme). Palladium catalysis
requires soft nucleophiles to ensure high
stereo- and regioselectivity, whereas hard
nucleophiles such as Grignard and orga-
nozinc reagents may be used under
copper catalysis. Vast progress during the
last decade reveals the promising future
of copper catalysis in this asymmetric
transformation.
Books
Highlights
Medicinal Chemistry
T. Larsen, A. Link*
4432 – 4434
A Timely Reassessment of Early Prediction
in the Bioavailability of Orally
Administered Drugs
Asymmetric Synthesis
H. Yorimitsu,* K. Oshima*
4435 – 4439
Recent Progress in Asymmetric Allylic
Substitutions Catalyzed by Chiral Copper
Complexes
4416
2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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Angew. Chem. Int. Ed. 2005, 44, 4416 – 4426
Angewandte
Chemie
Reviews
Synthetic Methods
K. C. Nicolaou,* P. G. Bulger,
D. Sarlah
4442 – 4489
Palladium-Catalyzed Cross-Coupling
Reactions in Total Synthesis
The virtues of the palladium-catalyzed
cross-coupling reactions come alive in
this stimulating Review article as the
authors highlight a number of total
syntheses featuring these important
carbon–carbon bond-forming reactions.
Synthethic Methods
K. C. Nicolaou,* P. G. Bulger,
D. Sarlah
4490 – 4527
Metathesis Reactions in Total Synthesis
The benefits of metathesis reactions
(alkene, enyne, and alkyne) are made
apparent in this stimulating Review arti-
cle. The authors highlight a number of
total syntheses featuring these important
carbon–carbon bond-forming reactions.
Communications
Sensors
N. A. Rakow, A. Sen, M. C. Janzen,
J. B. Ponder, K. S. Suslick*
4528 – 4532
Seeing smells: Highly selective discrimination between closely related amines has
been demonstrated by using an array of
chemoresponsive dyes (see picture).
Hierarchical classification of amines
based on their colorimetric response is
successful and matches that expected
from qualitative structural and electronic
considerations. High sensitivity
(ca. 100 ppbv) has been shown for the
detection and discrimination of amines.
For the USA and Canada:
ANGEWANDTE CHEMIE International
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individuals who are personal members of a
Angew. Chem. Int. Ed. 2005, 44, 4416 – 4426
www.angewandte.org
Molecular Recognition and
Discrimination of Amines with a
Colorimetric Array
national chemical society, or whose institution
already subscribes, or who are retired or selfemployed consultants, print only: US$ 394.00.
Postage and handling charges included. All
Wiley-VCH prices are exclusive VAT.
2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
4417
Angewandte
Chemie
Complete removal of interstitial water
molecules from various foam films of
amphiphilic compounds results in selfstanding bilayer membranes. The dried
foam films (DFFs) in the micrometer to
submicrometer range (see picture) are
stable even under ultrahigh-vacuum conditions and at temperatures higher than
100 8C.
Dried Foam Films
J. Jin, J. Huang, I. Ichinose* 4532 – 4535
Dried Foam Films: Self-Standing, WaterFree, Reversed Bilayers of Amphiphilic
Compounds
Green Chemisty
A new concept for catalytic reactions in
aqueous media is demonstrated by using
a temperature-responsive polymer support, poly(N-alkylacrylamide), which is
converted into a catalyst by assembly with
phosphotungstic acid. At high tempera-
ture, the catalyst is highly active in the
oxidation of alcohols with H2O2 owing to
the formation of emulsions, whereas the
product and catalyst are easily separated
at low temperature (see scheme).
H. Hamamoto, Y. Suzuki, Y. M. A.
Yamada, H. Tabata, H. Takahashi,
S. Ikegami*
4536 – 4538
A Recyclable Catalytic System Based on a
Temperature-Responsive Catalyst
Heterogeneous Catalysis
S. Zhou, B. Varughese, B. Eichhorn,*
G. Jackson, K. McIlwrath
4539 – 4543
Cores to celebrate: At 370 8C, Pt@Cu
core–shell nanoparticles rapidly alloy but
the reciprocal core–shell nanoparticles,
Cu@Pt (see STEM images, left: Cu spec-
Pt–Cu Core–Shell and Alloy Nanoparticles
for Heterogeneous NOx Reduction:
Anomalous Stability and Reactivity of a
Core–Shell Nanostructure
tral map; middle: Pt spectral map;
right: bright-field image), are kinetically
stabilized and show high activity and
selectivity for NO reduction.
Stuck in the middle: Supramolecular
host–guest cages of general formula
[BF4(RCN)2Co2L4](BF4)3 with L being a
di(benzimidazole)-1,4-phenylene derivative (R = Me, Et, Ph) have been prepared.
An encapsulated BF4 anion (B yellow,
F pale green; see structure) is locked
firmly inside the cage and plays a pivotal
role as a template around which the CoII
ions (gray) and L ligands (ball-and-stick
representation) self-assemble.
Angew. Chem. Int. Ed. 2005, 44, 4416 – 4426
www.angewandte.org
Host–Guest Chemistry
H. Amouri,* L. Mimassi, M. N. Rager,
B. E. Mann, C. Guyard-Duhayon,
L. Raehm
4543 – 4546
Host–Guest Interactions: Design Strategy
and Structure of an Unusual Cobalt Cage
That Encapsulates a Tetrafluoroborate
Anion
2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
4419
Contents
Combinatorial Chemistry
Generation of diversity: An oligosaccharide library can be constructed from glycopeptides by repeating incomplete glycosyltransferse (GTs) reactions in a single
tube (see picture). Each product has a
different molecular weight (MW). Therefore, the structure of each component in
the library can be identified immediately
by mass spectrometry alone. The differently colored shapes in the picture symbolize different glycosyl residues.
H. Ito, A. Kameyama, T. Sato, K. Kiyohara,
Y. Nakahara, H. Narimatsu* 4547 – 4549
Molecular-Weight-Tagged Glycopeptide
Library: Efficient Construction and
Applications
Imaging Agents
Strong photoluminescence in the blue
region of the visible spectrum was
observed for a dispersion of allylaminecapped silicon quantum dots in water.
Their ease of synthesis and optical properties make them excellent candidates for
biomedical applications, as demonstrated
by their incorporation inside the cytosol of
HeLa cells (see microscopy image, the
inset shows the fluorescence from the
silicon quantum dots on excitation with
UV light).
J. H. Warner, A. Hoshino, K. Yamamoto,
R. D. Tilley*
4550 – 4554
Water-Soluble Photoluminescent Silicon
Quantum Dots
Electrochemistry
R. Gill, F. Patolsky, E. Katz,
I. Willner*
A change in direction: The photocurrent
generated by CdS nanoparticles attached
by means of a double-stranded DNA
linker to a gold electrode is reversibly
switched between the anodic or cathodic
direction (see graphic) depending on the
redox state of the methylene blue intercalator.
4554 – 4557
Electrochemical Control of the
Photocurrent Direction in Intercalated
DNA/CdS Nanoparticle Systems
Supramolecular Chemistry
Any which way, but not loose: A range of
diverse noncovalent binding interactions
are observed with a [2]rotaxane (see
structure) and a [2]catenane that are not
found with similar but not mechanically
interlocked fragments. (C (macrocycle)
turquoise, other C atoms yellow, O red,
N blue, H gray, F green, S orange.)
D. A. Leigh,* P. J. Lusby, A. M. Z. Slawin,
D. B. Walker
4557 – 4564
Rare and Diverse Binding Modes
Introduced through Mechanical Bonding
4420
2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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Angew. Chem. Int. Ed. 2005, 44, 4416 – 4426
Angewandte
Chemie
Phase-Transfer Catalysis
A. Okada, T. Shibuguchi, T. Ohshima,*
H. Masu, K. Yamaguchi,
M. Shibasaki*
4564 – 4567
Optically active a,b-diamino acids are
prepared under asymmetric phase-transfer reaction conditions from a glycine
Schiff base and N-protected imines with a
tartrate-derived diammonium salt
(TaDiAS) as the phase-transfer catalyst
(see scheme; Boc = tert-butoxycarbonyl).
Chemoselective deprotection of the N
atoms allows straightforward transformations of the a,b-diamino acid products to
be carried out.
Enantio- and Diastereoselective Catalytic
Mannich-Type Reaction of a Glycine Schiff
Base Using a Chiral Two-Center PhaseTransfer Catalyst
A question of symmetry: Unlike other
mono-metallofullerenes, the cage structures of Eu@C82 (isomers I and III) have
been shown to have Cs (no. 6) and C2v
symmetry, respectively, by the maximum
entropy method using synchrotron X-ray
powder diffraction data. In both isomers
(see structures) the Eu ion (turquoise) is
located near the top of the carbon cage
adjacent to a C C double bond.
Structure Elucidation
B.-Y. Sun, T. Sugai, E. Nishibori, K. Iwata,
M. Sakata, M. Takata,
H. Shinohara*
4568 – 4571
An Anomalous Endohedral Structure of
Eu@C82 Metallofullerenes
Reaction Mechanisms
Finding the right pathway: Reaction of
isotopomers of ethylene with acetate
species (see scheme) adsorbed on a
Pd(111) surface in ultrahigh vacuum has
shown that vinyl acetate is produced by
insertion of ethylene into the acetate
species to form an acetoxyethyl intermediate, which decomposes by b-hydride
elimination to yield vinyl acetate.
D. Stacchiola, F. Calaza, L. Burkholder,
A. W. Schwabacher, M. Neurock,
W. T. Tysoe*
4572 – 4574
Elucidation of the Reaction Mechanism
for the Palladium-Catalyzed Synthesis of
Vinyl Acetate
Host–Guest Chemistry
V. Balzani,* P. Ceroni, C. Giansante,
V. Vicinelli, F.-G. KlLrner,* C. Verhaelen,
F. V/gtle,* U. Hahn
4574 – 4578
Tweezering the Core of a Dendrimer: A
Photophysical and Electrochemical Study
A large guest for a small host: The
tweezering process about the bipyridinium core of a dendrimer by a molecular
tweezer (see picture) has been studied
electrochemically and by fluorescence
Angew. Chem. Int. Ed. 2005, 44, 4416 – 4426
spectroscopy and is found to be quite
similar to the threading/dethreading processes observed with wire-type bipyridinium-based units and ring-shaped molecules.
www.angewandte.org
2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
4421
Contents
Nanotechnology
S. Moya, O. Azzaroni, T. Farhan,
V. L. Osborne,
W. T. S. Huck*
4578 – 4581
Locking and Unlocking of Polyelectrolyte
Brushes: Toward the Fabrication of
Chemically Controlled Nanoactuators
Protein Engineering
A. O. Magnusson, M. Takwa, A. Hamberg,
K. Hult*
4582 – 4585
An S-Selective Lipase Was Created by
Rational Redesign and the
Enantioselectivity Increased with
Temperature
Polymer brushwork: The collapse of polyelectrolyte brushes in salt solutions combined with binding interactions and ionsize-exclusion effects is used in the design
of smart polymer surfaces that can be
Higher activity with larger pockets: The
figure shows a superposition of intermediates that occur in acyl transfer to
(S)-1-phenylethanol catalyzed by Candida
antarctica lipase B (CALB). Wild-type
CALB cannot accomodate the phenyl
group (gray) in the stereospecificity
pocket and form all of the catalytically
essential H bonds. The Trp 104 Ala mutation liberates the volume in yellow, the
S enantiomer is easily fitted, and the
specificity constant increases by a factor
of 130 000.
Photocatalyis with Visible Light
Oxidative decomposition of toxic pollutants (such as acetaldehyde and isopropyl
alcohol), decomposition of water, and
photocurrent generation can all be
achieved with visible light. Nano-islands
of p-type CaFe2O4 interfacing with bulk
n-type PbBi2Nb1.9W0.1O9 (shown) form
photocatalytic nanodiodes that demonstrate high stability and high activity for
such applications.
H. G. Kim, P. H. Borse, W. Choi,
J. S. Lee*
4585 – 4589
Photocatalytic Nanodiodes for VisibleLight Photocatalysis
Mesoporous Films
M. Kuemmel, D. Grosso, C. BoissiOre,
B. Smarsly, T. Brezesinski, P. A. Albouy,
H. Amenitsch, C. Sanchez* 4589 – 4592
Thermally Stable Nanocrystalline
g-Alumina Layers with Highly Ordered
3D Mesoporosity
4422
switched between permanently collapsed
or extended states with different surface
properties (see picture)—a step toward
the use of surface-confined polyelectrolytes as nanoactuators.
Feature film: Mesoporous alumina thin
films synthesized with a polymeric template have more than 50% porosity, a
narrow pore-size distribution, high accessibility, and high thermal stability up to
9008C. The inorganic network is composed of sintered nanocrystalline g-Al2O3
particles, and the pores are ellipsoidal
with a face-centered cubic mesostructure
(see image).
2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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Angew. Chem. Int. Ed. 2005, 44, 4416 – 4426
Angewandte
Chemie
Bridging Ligands
Divalent Group 14 salts react with the
[Na(thf)x]+ derivative of the terminal niobium phosphide anion
[PNb{N(Np)Ar}3] (Np = neopentyl,
Ar = 3,5-Me2C6H3) to give complexes of
the form [(m2Dh3,h3-cyclo-EP2){Nb[N(Np)Ar]3}2] (E = Ge, Sn, and Pb; see
structure). The bridging {cyclo-EP2} units
in these complexes can be considered as
neutral 2p-electron three-membered rings
that are isolobal to the cyclopropenium
ion.
J. S. Figueroa,
C. C. Cummins*
4592 – 4596
Triatomic EP2 Triangles (E = Ge, Sn, Pb) as
m2Dh3,h3-Bridging Ligands
Glycopeptide Synthesis
D. A. Thayer, H. N. Yu, M. C. Galan,
C.-H. Wong*
4596 – 4599
A high-yield one-pot synthesis of S-linked
glycosyl amino acids 1 has been developed (see scheme; DMF = dimethyl formamide) and used in the solid-phase
synthesis of S-linked glycopeptides. This
approach has been shown to be efficient
for the synthesis of various S-linked
glycosyl amino acid building blocks.
A General Strategy toward S-Linked
Glycopeptides
Asymmetric Catalysis
B. Saito, T. Katsuki*
Quite universally: The chiral trigonalbipyramidal Al(salalen) complex 1 was
synthesized and found to be an efficient
catalyst for enantioselective hydrophosphonylation of various aldehydes with
dimethyl phosphite (see scheme). This is
the first example where a molecular
catalyst can be applied to the reactions of
both aromatic and aliphatic aldehydes
with enantioselectivities greater than
80 % ee.
A natural product anticipated through
total synthesis! Ocellapyrone A was
obtained in the laboratory several months
before the structure of this unusual natural product (see scheme) was reported.
An isomerization/8p–6p electrocyclization cascade was used for the formation of
the natural product from a polyene precursor. The synthesis of ocellapyrone B
from a diastereomer of ocellapyrone A
was also performed.
Angew. Chem. Int. Ed. 2005, 44, 4416 – 4426
www.angewandte.org
4600 – 4602
Synthesis of an Optically Active
C1-Symmetric Al(salalen) Complex and
Its Application to the Catalytic
Hydrophosphonylation of Aldehydes
Natural Products Synthesis
A. K. Miller, D. Trauner*
4602 – 4606
Mining the Tetraene Manifold:
Total Synthesis of Complex Pyrones from
Placobranchus ocellatus
2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
4423
Contents
Asymmetric Catalysis
C. Schaefer, G. C. Fu*
4606 – 4608
Catalytic Asymmetric Couplings of
Ketenes with Aldehydes To Generate
Enol Esters
With a little help from the ferrocenyl
catalyst (( )-1), a wide array of a-arylalkanoic acid derivatives can be produced
from the catalytic asymmetric coupling of
ketenes with aldehydes (see scheme). The
enol esters are readily transformed into
other useful families of compounds such
as carboxylic acids and alcohols.
Ever-increasing circles: Seven-memberedring ketones are constructed by a rhodium(i)-catalyzed arylative ring-expansion
reaction of alkyne-substituted aryl cyclo-
butanones, in which two C C bond-forming and one C C bond-cleaving events
occur consecutively (see scheme).
Two is better than one: Novel chiral
phosphine–olefin ligands 1 a and 1 b act
as bidentate ligands with some transition
metals and have proved to be highly
effective in the rhodium-catalyzed
asymmetric 1,4-addition of aryl boronic
acids to maleimides with high enantioselectivity (see scheme).
Organic Synthesis
T. Matsuda, M. Makino,
M. Murakami*
4608 – 4611
Synthesis of Seven-Membered-Ring
Ketones by Arylative Ring Expansion of
Alkyne-Substituted Cyclobutanones
Addition Reactions
R. Shintani, W.-L. Duan, T. Nagano,
A. Okada, T. Hayashi*
4611 – 4614
Chiral Phosphine–Olefin Bidentate
Ligands in Asymmetric Catalysis:
Rhodium-Catalyzed Asymmetric
1,4-Addition of Aryl Boronic Acids to
Maleimides
Host–Guest Systems
A stable environment: A [Cu(NH3)2]22+ dimer with weak cuprophilicity
is stabilized in the cavities of a supramolecular framework (see structure). This
Cui dimer is otherwise unstable, so stabilization within a supramolecular matrix
offers an unprecedented opportunity for
systematic studies of the isolated dimeric
species, either in the ground state or the
excited state.
S.-L. Zheng,* M. Messerschmidt,
P. Coppens*
4614 – 4617
An Unstable Ligand-Unsupported
Cui Dimer Stabilized in a Supramolecular
Framework
4424
2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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Angew. Chem. Int. Ed. 2005, 44, 4416 – 4426
Angewandte
Chemie
A sulfide surprise: The analysis of ZnII–,
CdII–, and CuI–MT recombinant preparations of metallothioneins (MTs) from
many organisms provides clear evidence
that sulfide ions are present in nearly all
their physiologically stable ZnII–MT and
CdII–MT complexes (see picture), but in
none of the CuI–MT species. The features
of the MT complexes are in good correla-
Lost control: The rationalization of the
ambident reactivity of NO2 by the change
between charge control to orbital control
has to be revised. SN1-type reactions of
Bioinorganic Chemistry
M. Capdevila,* J. DomOnech, A. Pagani,
L. TTo, L. Villarreal, S. Atrian 4618 – 4622
Zn– and Cd–Metallothionein
Recombinant Species from the Most
Diverse Phyla May Contain Sulfide (S2 )
Ligands
tion with those reported for plant and
yeast ZnII– or CdII–g-glutamyl peptides.
carbocations with NO2 give kinetically
controlled product mixtures only when
these reactions proceed without activation energy (diffusion control). Activationcontrolled SN1 alkylations are reversible
and lead to the thermodynamically more
stable nitro compounds.
Ambident Anions
A. A. Tishkov, U. Schmidhammer, S. Roth,
E. Riedle, H. Mayr*
4623 – 4626
Ambident Reactivity of the Nitrite Ion
Revisited
Asymmetric Synthesis
H. Leuser, S. Perrone, F. Liron,
F. F. Kneisel, P. Knochel*
4627 – 4631
Trisubstituted allylic pentafluorobenzoates react with diorganozinc reagents in
the presence of CuCN·2 LiCl to provide
alkenes bearing a chiral quaternary center
in a position (> 95 % ee). These alkenes
are readily converted into chiral tertiary
alcohols or into chiral amino alcohols by a
straightforward sequence of ozonolysis
followed by Curtius rearrangement (see
scheme).
Protein Folding
Launching a probe: Introducing individual
tyrosine residues labeled with 13C at the C4
position of the phenol ring (Y11 and Y19
in the picture) shifts the resulting tyrosine
IR band to lower frequencies. This opens
the door to the simultaneous monitoring
of local conformational changes in different regions of proteins by IR spectroscopy,
as demonstrated with a chemically synthesized analogue of a WW domain.
Angew. Chem. Int. Ed. 2005, 44, 4416 – 4426
Highly Enantioselective Preparation of
Tertiary Alcohols and Amines by CopperMediated Diastereoselective Allylic SN2’
Substitutions
S. Tremmel,* M. Beyermann,
H. Oschkinat, M. Bienert, D. Naumann,
H. Fabian*
4631 – 4635
13
C-Labeled Tyrosine Residues as Local IR
Probes for Monitoring Conformational
Changes in Peptides and Proteins
www.angewandte.org
2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
4425
Contents
Molecular Devices
V. A. Azov, A. Schlegel,
F. Diederich*
A molecular switch based on a resorcin[4]arene cavitand undergoes reversibly
very large, geometrically precisely defined
molecular motion (see picture). Controlled switching between the contracted
(linear extension 7 V) and the expanded
(linear extension 7 nm) states is
induced by pH or temperature changes
and was observed by 1H NMR spectroscopy and fluorescence resonance energy
transfer (FRET).
4635 – 4638
Geometrically Precisely Defined
Multinanometer Expansion/Contraction
Motions in a Resorcin[4]arene Cavitand
Based Molecular Switch
The issues for July 2005 appeared online on the following dates
Issue 25: June 10 · Issue 26: June 17 · Issue 27: June 23 · Issue 28: July 4
Service
Keywords
4640
Authors
4641
Angewandte’s
Sister Journals
Vacancies
Preview
4426
2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.angewandte.org
4642 – 4643
A42
4645
Angew. Chem. Int. Ed. 2005, 44, 4416 – 4426
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