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Graphical Abstract Angew. Chem. Int. Ed. 312004

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Contents
The following Communications are available online (in Wiley InterScience). You can find them, as
well as forthcoming Reviews, Highlights, and Essays, at www.angewandte.org, under Early View.
M. Tanaka,* Y. Demizu, M. Doi, M. Kurihara, H. Suemune*:
Chiral Centers in the Side Chains of a-Amino Acids Control the
Helical Screw Sense of Peptides
DOI: 10.1002/anie.200460420
Published online: July 7, 2004
M. Finze, E. Bernhardt, H. Willner,* C. W. Lehmann:
[(CF3)3BCP] and [(CF3)3BCAs] : Thermally Stable Phosphaethynyl and Arsaethynyl Complexes
DOI: 10.1002/anie.200454034
Published online: July 14, 2004
Articles judged by the referees or the editor as being either very important or very urgent are immediately edited, proof-read, and electronically
published once the manuscript has arrived in the editorial office in its 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
Crystallographers Honor W.
Saenger
Novartis Award to R. Micura
3994
3994
J. S. Miller Receives Utah Award of the
ACS
3994
Books
Reactive Intermediate Chemistry
3995
Carbohydrate-Based Drug
Discovery
3995
Robert A. Moss, Matthew S. Platz,
Maitland Jones, Jr.
reviewed by G. Bucher
Chi-Huey Wong
reviewed by O. Plettenburg, U. Stilz
Highlights
Dedifferentiation
C. Gey, A. Giannis*
The name is the game. Reversine (1) is a
low-molecular-weight compound that
reverses the process of cell differentiation
in mammals. Specialized muscle cells can
be transformed into multipotent progenitor cells. This approach may have potential for targeted regeneration processes in
humans.
3998 – 4000
Small Molecules, Big Plans—Can LowMolecular-Weight Compounds Control
Human Regeneration?
Minireviews
Solventless Reactions
D. Braga,* F. Grepioni
4002 – 4011
Reactions Between or Within Molecular
Crystals
3986
Weaning chemistry onto solids: reactions
between solids (see picture) are often
regarded as oddities and mechanical
synthetic methods are felt to be fundamentally “nonchemical”. This attitude is
changing as solvent-free conditions
become more important in environmentally friendly processes. In addition, solidstate synthetic procedures are often viable
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.angewandte.org
alternative routes to known products and
also to new compounds not obtainable by
traditional solution chemistry.
Angew. Chem. Int. Ed. 2004, 43, 3986 – 3992
Angewandte
Chemie
Reviews
Through the membrane: The antigen
transporter complex TAP plays a pivotal
role in the translocation machinery which
pumps antigenic peptides from the cytosol into the ER, a requirement for entry
into the secretory pathway and
subsequent display on the cell surface.
Structural and mechanistic aspects of this
ABC transporter are of great interest in
membrane biology, immunology, virology,
and cell biology. The picture shows the
nucleotide binding domain of human
TAP1.
Immunology
S. Beismann-Driemeyer,
R. Tamp@*
4014 – 4031
Function of the Antigen Transport
Complex TAP in Cellular Immunity
Communications
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ANGEWANDTE CHEMIE International
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Angew. Chem. Int. Ed. 2004, 43, 3986 – 3992
Peptides sandwiched to order: Genetic
engineering can be used to prepare
charged polypeptides that self-assemble
with oppositely charged surfactants into
highly ordered multilayers (see diagram).
Nanoscale order on three separate length
scales can be controlled in the polyelectrolyte–surfactant self-assemblies by
changing the peptide length, charge, and
surfactant composition.
Nanostructures
Three complexes from one reaction: The
reaction of N-(2-hydroxyethyl)iminodiacetic acid with Ga(NO3)3 yields an alkoxobridged dimer, a Ga8 cluster (see picture),
and a Ga13 cluster. The structures of these
complexes and the structural relationships between them are reported, and the
insight they may shed on the general
mechanism of cluster formation is discussed.
Gallium Clusters
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Chemie, Wiley-VCH, 111 River Street, Hoboken,
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www.angewandte.org
I. Koltover,* S. Sahu,
N. Davis
4034 – 4037
Genetic Engineering of the Nanoscale
Structure in Polyelectrolyte–Lipid
Self-Assembled Systems
J. C. Goodwin, S. J. Teat,
S. L. Heath*
4037 – 4041
How Do Clusters Grow? The Synthesis
and Structure of Polynuclear Hydroxide
Gallium(iii) Clusters
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
3987
Contents
Inhibitor Design
S. Gilead, E. Gazit*
4041 – 4044
Inhibition of Amyloid Fibril Formation
by Peptide Analogues Modified with
a-Aminoisobutyric Acid
Multichromophoric Polymers
J. Hernando, P. A. J. de Witte,
E. M. H. van Dijk, J. Korterik,
R. J. M. Nolte, A. E. Rowan,
M. F. GarcLa-ParajM,*
N. F. van Hulst
4045 – 4049
Investigation of Perylene Photonic Wires
by Combined Single-Molecule Fluorescence and Atomic Force Microscopy
Chiral Oligomers
X. Ribas, J. C. Dias, J. Morgado, K. Wurst,
M. Almeida, T. Parella, J. Veciana,
C. Rovira*
4049 – 4052
Stepwise Construction of Oligomeric
1,2-Diselenolene Platinum(iv) Complexes
Breaking up is not hard to do with an
a-aminoisobutyric (Aib) acid b-breaker,
which has a remarkably restricted conformation. A novel approach to the inhibition
of amyloid formation was developed that
uses peptides modified with Aib (see
figure). The similarity of Aib to hydrophobic amino acids, often found in amyloidogenic sequences, allows its integration into recognition motifs.
Heterogeneous optical behavior of perylene polyisocyanides, which arises from
different structures of the polymer backbone, is revealed by the combination of
single-molecule fluorescence spectroscopy and atomic force microscopy. Short
nonhelical perylene oligomers exhibit
monomer-like fluorescence properties,
whereas long helical perylene fiber emission arises from excimer sites after
Surrounded by selenium: Pulse field gradient spin-echo (PGSE) NMR diffusion
studies of a mixture of oligomeric 1,2diselenolene PtIV complexes are performed to characterize the species in
solution (see structure: n = 0 (1), n = 1
(2), n = 2 (3); red Pt, green Se, blue N,
gray C). The results are in accord with the
single-crystal X-ray diffraction structures
obtained for the chiral complexes {PtIVSe6}
(1) and {PtIV2Se10} (2).
Complementary-DNA Phage Display
Putting on a good display: A novel
selection protocol was devised for the
simultaneous display cloning of three
homologues of the FK506-binding protein
(FKBP12, FKBP12.6, and FKBP13) by
using AP1497 (see structure), a mimetic
of FK506, and a T7 complementary-DNA
phage-display library. A quantitative onphage binding assay was also performed
to evaluate the affinity of the isolated
proteins.
K. M. McKenzie, E. J. Videlock,
U. Splittgerber,
D. J. Austin*
4052 – 4055
Simultaneous Identification of Multiple
Protein Targets by Using ComplementaryDNA Phage Display and a NaturalProduct-Mimetic Probe
3988
delocalization of the excitation along the
polymer backbone (see picture).
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.angewandte.org
Angew. Chem. Int. Ed. 2004, 43, 3986 – 3992
Angewandte
Chemie
Conformation Analysis
R. Baron, D. Bakowies,
W. F. van Gunsteren*
4055 – 4059
Carbopeptoid Folding: Effects of Stereochemistry, Chain Length, and Solvent
Shaping up nicely: Carbopeptoids with
THF rings in their backbone show distinct
folding behavior depending on chain
length, configuration, and solvent polarity.
Molecular dynamics simulations of the
folding yield averaged proton–proton
distances in good agreement with experimental NOE data. They show, however,
that a number of folds are important
(b–d), whereas NOE data are usually
interpreted in terms of single structures
(a).
Organic Nanostructures
Z. Tian, Y. Chen, W. Yang, J. Yao,* L. Zhu,
Z. Shuai
4060 – 4063
Low-Dimensional Aggregates from
Stilbazolium-Like Dyes
Dye hard: Strong intermolecular interactions of stilbazolium-like dyes with different structures and conformations seem to
act as the main driving force for the
formation of nanostructures with distinct
morphological and spectral properties.
Nanorods and nanospheres (see picture)
with well-defined shapes and uniform
sizes are formed by changing the solvent
quality during synthesis.
Heterocycle Synthesis
Y. Terada, M. Arisawa,*
A. Nishida*
Substituted N and O heterocycles have
been synthesized by the cycloisomerization of dienes using a ruthenium-carbene
catalyst. The products obtained with and
Unmasking the potential: A DNA-templated nanofabrication approach is
reported in which various 1D and 2D DNA
nanostructures were assembled, and then
these structures transformed into corresponding metal nanostructures through
metal deposition (see schematic representation). The ease and flexibility of this
Angew. Chem. Int. Ed. 2004, 43, 3986 – 3992
without trimethylsilyl vinyl ether differ (see
scheme, Cy = cyclohexyl, Mes = 2,4,6-trimethylphenyl, Ts = p-toluenesulfonyl).
4063 – 4067
Cycloisomerization Promoted by the
Combination of a Ruthenium–Carbene
Catalyst and Trimethylsilyl Vinyl Ether, and
its Application in The Synthesis of
Heterocyclic Compounds: 3-Methylene2,3-dihydroindoles and 3-Methylene2,3-dihydrobenzofurans
Metallic Nanostructures
Z. Deng, C. Mao*
technique offers a route to overcome the
inabilities faced by traditional lithographic
techniques.
www.angewandte.org
4068 – 4070
Molecular Lithography with DNA
Nanostructures
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
3989
Contents
Proteomics Research
M. Kurogochi, T. Matsushita,
S.-I. Nishimura*
4071 – 4075
Post-Translational Modifications on
Proteins: Facile and Efficient Procedure
for the Identification of O-Glycosylation
Sites by MALDI-LIFT-TOF/TOF Mass
Spectrometry
We have LIFT-TOF! Transglycosylation of
glycopeptides by b-galactosidase in the
presence of lactose combined with
tandem mass spectrometry using a 2,5dihydroxybenzoic acid matrix enables the
O-glycosylation sites to be identified (see
Asymmetric Catalysis
scheme). The highly sensitive and ideal
fragmentation patterns generated from
glycopeptide precursor ion peaks can be
readily used for precise and reliable
structure analyses.
The direction and degree of enantioselectivity in the cyclohexanone monooxygenase catalyzed air-mediated Baeyer–Villiger reactions, such as the desymmetrization of 1, can be controlled by directed
evolution.
M. T. Reetz,* B. Brunner, T. Schneider,
F. Schulz, C. M. Clouthier,
M. M. Kayser
4075 – 4078
Directed Evolution as a Method To Create
Enantioselective Cyclohexanone Monooxygenases for Catalysis in Baeyer–Villiger
Reactions
Asymmetric Catalysis
M. T. Reetz,* F. Daligault, B. Brunner,
H. Hinrichs, A. Deege
4078 – 4081
Directed Evolution of Cyclohexanone
Monooxygenases: Enantioselective Biocatalysts for the Oxidation of Prochiral
Thioethers
Mutational changes in cyclohexanone
monooxygenases (CHMOs), for example
the introduction of serine at position 432,
lead to surprisingly versatile enantiose-
lective biocatalysts that perform particularly well in the air-mediated partial oxidation of prochiral thioethers (see
scheme).
Hydrosilylation by H-terminated silicon of
the double bond of methyl 10-undecenoate with formation of a robust Si C
bond is the first step in a three-step
procedure (see scheme) for anchoring the
single-molecule magnet (SMM)
[Mn12O12(OAc)16(H2O)4] (1) on the
Si(100) surface.
Single-Molecule Magnets on Silicon
G. G. Condorelli, A. Motta, I. L. FragalR,*
F. Giannazzo, V. Raineri, A. Caneschi,
D. Gatteschi
4081 – 4084
Anchoring Molecular Magnets on the
Si(100) Surface
3990
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.angewandte.org
Angew. Chem. Int. Ed. 2004, 43, 3986 – 3992
Angewandte
Chemie
Homogeneous Catalysis
A mixed complex which results from two
salen-derived VV and TiIV complexes (1
and 2), catalyzes the trimethylsilylcyanation of aldehydes. The reaction kinetics
are largely determined by the titaniumderived portion, whereas the configuration of the mandelonitrile trimethylsilyl
ether products is determined by the
slower vanadium part of the catalyst.
salen = N,N’-bis(salicylaldehydo)ethylenediamine.
Yu. N. Belokon,* M. North, V. I. Maleev,
N. V. Voskoboev, M. A. Moskalenko,
A. S. Peregudov, A. V. Dmitriev,
N. S. Ikonnikov,
H. B. Kagan*
4085 – 4089
In Situ Formation of a Heterobimetallic
Chiral [(Salen)TiIV]/[(Salen)VV] Catalyst for
the Asymmetric Addition of TMSCN to
Benzaldehyde
Carbenes
From amides to carbenes: Phosphoniosubstituted iminium salts are readily
available from the corresponding amides
in a one-pot reaction. Deprotonation
followed by substitution reactions affords
a variety of transient and stable amino
carbenes (see scheme).
S. Conejero, Y. Canac, F. S. Tham,
G. Bertrand*
4089 – 4093
Readily Available Onio-Substituted
Methyleneiminium Salts: Single
Precursors for a Variety of Aminocarbenes
Phosphorus Radicals
J. Geier, J. Harmer,
H. GrVtzmacher*
Encapsulation of the Na+ ions of the
[Na2(P4R4)] ion triple with a R,R or
S,S configuration at the inner phosphorus
atoms by cryptands has enabled cationseparated dianions to be obtained in a
crystalline form. Fragmentation of the
{Na([2.2.2]cryptand)}2(P4R4) into radical
anions (P2R2)C occurs in solution (see
scheme), as determined by EPR
spectroscopy.
“Naked” Phosphanediide Chains and
their Fragmentation into Diphosphene
Radical Anions
Enzymatic Oxidation
Bound to do the job: Sol–gel methods
have been used to encapsulate chloroperoxidase (CPO) in microporous silica.
The encapsulated CPO can then be used
as an enantioselective catalyst for the
oxidation of organic sulfides (see scheme)
and can be recycled without appreciable
loss of activity and enantioselectivity.
Angew. Chem. Int. Ed. 2004, 43, 3986 – 3992
4093 – 4097
V. Trevisan, M. Signoretto, S. Colonna,
V. Pironti, G. Strukul*
4097 – 4099
Microencapsulated Chloroperoxidase as a
Recyclable Catalyst for the Enantioselective Oxidation of Sulfides with
Hydrogen Peroxide
www.angewandte.org
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
3991
Contents
Alkene Hydrazination
J. Waser, E. M. Carreira*
4099 – 4102
Catalytic Hydrohydrazination of a Wide
Range of Alkenes with a Simple Mn
Complex
Enhanced activity, lower catalyst loading,
shorter reaction times, and expanded
substrate scope are the advantages of
[Mn(dpm)3] over Co catalysts in the
hydrohydrazination reaction of alkenes
(see scheme). Thus, sterically hindered
alkenes, including tetrasubstituted
alkenes, can now also readily undergo this
reaction.
Communications labeled with this symbol have been judged by two referees as being “very important papers”.
Service
Keywords
4104
Authors
4105
Angewandte’s
Sister Journals
Preview
3992
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.angewandte.org
4106 – 4107
4109
Angew. Chem. Int. Ed. 2004, 43, 3986 – 3992
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