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Graphical Abstract Angew. Chem. Int. Ed. 272003

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Contents
The following articles are available online (in Wiley Interscience). You can find them at
www.angewandte.org, under Full Text, Forthcoming Articles.
F. Wrthner,* S. Yao, U. Beginn:
Highly Ordered Merocyanine Dye Assemblies by Supramolecular
Polymerization and Hierarchical Self-Organization
DOI: 10.1002/anie.200351414
Published online: July 3, 2003
R. R. Davda, J. A. Dumesic*:
Catalytic Reforming of Oxygenated Hydrocarbons for Hydrogen
with Low Levels of Carbon Monoxide
DOI: 10.1002/anie.200351664
Published online: June 18, 2003
Articles judged by the referees or the editior as being either very important or very urgent are immediately edited, proof-read, and electronically
published once the manuscript has arrived in the editiorial office in final form. As long as there is no page number available these articles should be
cited in the following manner:
Author(s) Angew. Chem. Int. Ed., online publication date, DOI.
News
Physical Chemistry:
Prizes for Ertl
3064
Inorganic Chemistry:
Oro Recognized
3065
Evolution of the Ribosome
Burkhard Luy
Cohesion
3066
John S. Rowlinson
reviewed by Ralf Ludwig
Organic Synthetic Methods
3067
James R. Hanson
reviewed by A. Stephen K. Hashmi
3064
Organic Chemistry:
Brgenstock Brief
3064
Web Sites
http://www.rna.icmb.utexas.edu
Books
Highlights
Biosynthesis of Fungal Alkaloids
F. von Nussbaum*
With its 15 rings, stephacidin B (see
structure) is one of the most complex
indole alkaloids to be isolated from fungi.
The pseudosymmetric structure indicates
that a new type of dimerization takes
place at a late stage of the biosynthesis.
3068 – 3071
Stephacidin B—A New Stage of
Complexity within Prenylated Indole
Alkaloids from Fungi
Bioactive Hydrogelators
J. C. Tiller*
3072 – 3075
Increasing the Local Concentration of
Drugs by Hydrogel Formation
3056
Drugs that gel: The first hydrogel-forming
drug, a pyrene-derivatized form of the
antibiotic vancomycin (see structure),
exhibits an 11-fold higher antimicrobial
activity than vancomycin itself. A possible
mechanism for this effect and its influence on future drug design are discussed.
2003 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.angewandte.org
Angew. Chem. Int. Ed. 2003, 42, 3056 – 3062
Angewandte
Chemie
Reviews
HO
O
SEnz
Me
Me
O
Diels-Aldercyclization
SEnz
Me
Me
E. M. Stocking,
R. M. Williams*
O
Me
Me
3078 – 3115
Chemistry and Biology of Biosynthetic
Diels–Alder Reactions
Me
lovastatin
Do they or don’t they? A Diels–Alder
cycloaddition has been assumed to occur
in the biosynthesis of numerous natural
products, for example, lovastatin (see
scheme). The existence of enzymes that
Biosynthetic Diels–Alder Reactions
O
O
Me
O
catalyze these reactions (Diels–Alderases)
was until recently not know for certainty,
even when biosynthetic investigations and
the biommetic total syntheses in some
cases suggested it to be so.
Communications
Towards Influenza Detection
J. L. McKimm-Breschkin,* P. M. Colman,
B. Jin, G. Y. Krippner, M. McDonald,
P. A. Reece, S. P. Tucker, L. Waddington,
K. G. Watson,* W.-Y. Wu
3118 – 3121
Catching flu: The influenza virus neuraminidase inhibitor zanamivir (red) is
functionalized at the 7-position to give
derivatives that retain a high affinity for
Tethered Neuraminidase Inhibitors That
Bind an Influenza Virus: A First Step
Towards a Diagnostic Method for
Influenza
the enzyme. When conjugated to biotin
(green) or onto microspheres, such
derivatives can be used to capture or
aggregate influenza virus particles.
Electrochemical Transduction
W.-S. Yeo, M. Mrksich*
3121 – 3124
Self-Assembled Monolayers That
Transduce Enzymatic Activities to
Electrical Signals
A dynamic substrate that transduces a
biological activity into an electrical signal
has been developed (see scheme). The
enzymatic conversion of a redox-inactive
substrate presented at a self-assembled
monolayer produced a redox-active product that is monitored electrochemically in
real time.
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Angew. Chem. Int. Ed. 2003, 42, 3056 – 3062
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delivery); for individuals who are personal
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2003 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
3057
Contents
Polypropionate Synthesis
E. Torres, Y. Chen, I. C. Kim,
P. L. Fuchs*
3124 – 3131
Functionality Propagation by Alkylative
Oxidation of Cross-Conjugated
Cycloheptadienyl Sulfones
Getting the most out of sulfur. Enantiopure epoxyvinyl sulfone 1 is transformed
to syn- and anti-dienyl sulfones 2 and 3,
respectively, by means of a nucleophilic
methylation/sulfenylation/directed elimination reaction sequence. Compound 2
has been converted into termini-differentiated seven-carbon polypropionate
segments found in five biologically significant natural products.
Asymmetric Azidoselenenylation
M. Tiecco,* L. Testaferri, C. Santi,
C. Tomassini, F. Marini, L. Bagnoli,
A. Temperini
3131 – 3133
Asymmetric Azidoselenenylation of
Alkenes: A Key Step for the Synthesis of
Enantiomerically Enriched NitrogenContaining Compounds
Chiral, nonracemic azidoselenides such as
2 are useful intermediates for the synthesis of enantiomerically enriched nitrogen-containing compounds (e.g. 3). The
asymmetric electrophilic azidoselenenylation of a variety of alkenes with the
Trifluoromethylation
Both non-enolizable and enolizable carbonyl compounds underwent nucleophilic
trifluoromethylation by a new family of
cheap and efficient trifluoroacetamide
reagents derived from vic-amino alcohols
(see picture). From an ecological and an
economic viewpoint these represent a
promising alternative to other known
trifluoromethylation reagents.
J. Joubert, S. Roussel, C. Christophe,
T. Billard,* B. R. Langlois,*
T. Vidal
3133 – 3136
Trifluoroacetamides from Amino Alcohols
as Nucleophilic Trifluoromethylating
Reagents
sulfur-containing chiral selenenyl triflate 1
and sodium azide occurred with high
facial selectivity to provide an array of
azidoselenides, which were further
elaborated.
Probing Fullerene Aromaticity
T. Sternfeld, M. Saunders, R. J. Cross,
M. Rabinovitz*
3136 – 3139
The Inside Story of Fullerene Anions:
A 3He NMR Aromaticity Probe
Fullerene anions with helium atoms contained inside the cage exhibit degrees of
aromaticity that can be predicted through
the measurement of 3He chemical shifts
(see picture). These chemical shifts help
3058
2003 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.angewandte.org
to demonstrate that the magnetic properties of fullerenes, and their anions, are
not simply related to the number of
carbon atoms or the number of electrons
in the p system.
Angew. Chem. Int. Ed. 2003, 42, 3056 – 3062
Angewandte
Chemie
A fast switch: A covalent molecular tetrad
(see picture), consisting of two electron
donor/acceptor pairs acts as a high-speed
molecular AND gate when it is sequentially excited using laser pulses having two
different wavelengths. This system of
using two sequential photodriven electron
transfers is analogous to photosystems I
and II in green plants which act in series
to separate charge for long periods of
time.
Logic Gates
M. Andersson, L. E. Sinks, R. T. Hayes,
Y. Zhao, M. R. Wasielewski* 3139 – 3143
Bio-Inspired Optically Controlled Ultrafast
Molecular AND Gate
Asymmetric Cyanophosphorylation
A. Baeza, J. Casas, C. NJjera,*
J. M. Sansano, J. M. SaJ*
3143 – 3146
(R)- and (S)-binolam–AlCl complexes act
as bifunctional catalysts to mediate the
enantioselective cyanophosphorylation of
aldehydes at room temperature. The
resulting chiral cyanohydrin O-phosphates can be reduced to b-aminoalco-
Large cavities ( 10–12.3 nm) of cubic
(Fm-3m) mesoporous silica without
intergrowth are synthesized in the presence of block copolymer templates. The
entrance sizes of these cavities can be
adjusted in the range of 4–9 nm as
confirmed by nitrogen sorption studies
and an examination of the negative gold
replicas. The 3D open mesostructures
facilitate the transportation of biomolecules (see picture), as well as the repli-
hols or, when suitably substituted, can be
transformed into g-cyanoallylic alcohols
through palladium-catalyzed allylic substitution, without loss of enantiomeric
excess (see scheme).
Mesoporous Silica with Large Entrances
J. Fan, C. Yu,* F. Gao, J. Lei, B. Tian,
L. Wang, Q. Luo, B. Tu, W. Zhou,
D. Zhao*
3146 – 3150
cation of a large-pore (9 nm) cubic mesoporous carbon.
Four negative charges at the entrance of a
deep pocket, lined with aromatic residues
are the features of a synthetic receptor
which shows high affinity for acetylcholine
(see picture) and choline in water. The
size, shape, and charge recognition elements featured in the natural enzyme
acetylcholinesterase are reproduced by
the synthetic receptor.
Angew. Chem. Int. Ed. 2003, 42, 3056 – 3062
Enantioselective Synthesis of Cyanohydrin
O-Phosphates Mediated by the
Bifunctional Catalyst Binolam–AlCl
www.angewandte.org
Cubic Mesoporous Silica with Large
Controllable Entrance Sizes and
Advanced Adsorption Properties
Choline Recognition in Water
F. Hof, L. Trembleau, E. C. Ullrich,
J. Rebek, Jr.*
3150 – 3153
Acetylcholine Recognition by a Deep,
Biomimetic Pocket
2003 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
3059
Contents
Gene Delivery Proteins
Higher delivery efficiency than conventional nonviral systems (such as poly(ethyleneimine)) have been identified in
46 polymers through cell-based screening
of a large, 2350-member library by a highthroughput, semi-automated process.
The transfection potential of the polymers
was assessed by testing their ability to
deliver luciferase expressing plasmid and
green fluorescent protein plasmid (see
picture) to a monkey kidney fibroblast cell
line.
D. G. Anderson, D. M. Lynn,
R. Langer*
3153 – 3158
Semi-Automated Synthesis and Screening
of a Large Library of Degradable Cationic
Polymers for Gene Delivery
Fullerene-Based Catenanes/Rotaxanes
Y. Nakamura, S. Minami, K. Iizuka,
J. Nishimura*
3158 – 3162
Preparation of Neutral [60]FullereneBased [2]Catenanes and [2]Rotaxanes
Bearing an Electron-Deficient Aromatic
Diimide Moiety
Crowning glory: An unprecedented
[2]catenane that exhibits a donor–
acceptor–donor–acceptor stacking motif
was obtained through intramolecular
Bingel reactions of [60]fullerene monoad-
Heterohelicene Derivatives
C. Herse, D. Bas, F. C. Krebs, T. Brgi,
J. Weber, T. Wesolowski, B. W. Laursen,*
J. Lacour*
3162 – 3166
A Highly Configurationally Stable
[4]Heterohelicenium Cation
A [4](hetero)helicenium cation was
resolved using the hexacoordinated
phosphorus-containing binphat anion
(see picture: N, blue; O, red; C, gray). Its
absolute configuration was determined
by vibrational circular dichroism
spectroscopy. The barrier of interconversion of its enantiomers is
higher than that of [6]helicene.
Triple-Stranded Helicates
Spiraling into control: A finite linear
arrangement of four magnetically
coupled copper(ii) centers has been
generated within a triple-stranded helical
motif that was formed through a strict
self-assembly process between a single
octadentate ligand and CuII ions (see
picture). This approach opens the way to
constructing finite one-dimensional
magnetic chains in a controlled manner.
C. J. Matthews,* S. T. Onions, G. Morata,
L. J. Davis, S. L. Heath,
D. J. Price
3166 – 3169
A Self-Assembled Tetracopper TripleStranded Helicate: Towards the
Controlled Synthesis of Finite OneDimensional Magnetic Chains
3060
ducts that bear a naphthalenetetracarboxylic diimide moiety, in the presence
of 1,5-dinaphtho[38]crown-10 ether at
78 8C (see scheme; DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene).
2003 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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Angew. Chem. Int. Ed. 2003, 42, 3056 – 3062
Angewandte
Chemie
Parting the clouds: A supramolecular
recognition reaction of cyclodexdrins with
polymers—adamantyl derivative N-isopropylacrylamide copolymers—with
inverse phase behavior is described. The
turbidity of the polymer solutions
depends upon the cyclodextrin concentration. Competition reactions with
potassium-1-adamantylcarboxylate show
that the inclusion-complex formation is
reversible (see scheme).
Thermoreversible Polymers
H. Ritter,* O. Sadowski,
E. Tepper
3171 – 3173
Influence of Cyclodextrin Molecules on
the Synthesis and the Thermoresponsive
Solution Behavior of N-Isopropylacrylamide Copolymers with Adamantyl
Groups in the Side-Chains
Anomeric Protecting Groups
N. Pleuss, H. Kunz*
Reactivity upon demand: Because of their
stability towards acids, bases, and many
oxidizing and reducing agents, N-glycosyl
amides 1 (see scheme) can be used as
anomerically protected carbohydrates.
The amide function can be cleaved under
mild conditions with Ph3P/CBr4 and the
carbohydrate activated for the synthesis of
N- and O-glycosides 2. PG = protecting
group.
3174 – 3176
N-Glycosyl Amides: Removal of the
Anomeric Protecting Group and
Conversion into Glycosyl Donors
Shape Persistent Organic Ring
Ever increasing circles? The giant cycle 1
has a diameter of 12 nm making it the
largest, shape persistent and monodisperse cyclic molecular structure designed
and synthesized to date. A modular
approach consisting of a series of subsequent dimerization steps made 1 accessible.
M. Mayor,* C. Didschies
3176 – 3179
A Giant Conjugated Molecular Ring
Light converter: The emission of visible
light (Vis) upon excitation in the nearinfrared (NIR) has been observed for the
first time in a transparent solution. Excitation at 975 nm (marked red in the
picture) of optically clear colloidal solutions of LuPO4 :Yb3+, Tm3+, and
YbPO4 :Er3+ nanocrystals in chloroform
leads to visible upconversion luminescence in the blue, green, or red spectral
regions.
Upconversion of Photons
S. Heer, O. Lehmann, M. Haase,
H.-U. Gdel*
3179 – 3182
Blue, Green, and Red Upconversion
Emission from Lanthanide-Doped LuPO4
and YbPO4 Nanocrystals in a Transparent
Colloidal Solution
Communications labeled with this symbol have been judged by two referees as being “very important papers”.
The publication of Communications labeled with this symbol has been accelerated because of their topical or highly competitive
nature.
Angew. Chem. Int. Ed. 2003, 42, 3056 – 3062
www.angewandte.org
2003 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
3061
Contents
Service
3062
2003 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.angewandte.org
Keywords
3184
Authors
3185
Angewandte’s Sister Journals
3186
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3187
Angew. Chem. Int. Ed. 2003, 42, 3056 – 3062
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