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Mini-Reviews
in Organic Chemistry
ISSN: 1570-193X
Mini-Reviews
in Organic Chemistry
Volume 4, Number 4, November 2007
Contents
Pseudopeptide Synthesis via Fmoc Solid-Phase
Synthetic Methodology Pp. 268-280
Predrag Cudic and Maciej Stawikowski
[Abstract]
Conjugation of 1,4,7,10-Tetraazacyclododecane-1,4,
7,10 Tetracetic Acid (DOTA) and its Derivatives to Peptides:
Synthesis, Applications and Future Prospects Pp.
281-291
Z. Kovacs and L. M. De León-Rodríguez
[Abstract]
Supramolecular Chemistry with Phthalimide Derivatives
Pp. 292-309
Nilotpal Barooah and Jubaraj B. Baruah
[Abstract]
Mechanistic and Synthetic Aspects of the Benzilic
Acid and Ester Rearrangements Pp. 310-316
Anthony J. Burke and C.S. Marques
[Abstract]
Recent Developments and Trends in 18F-Radiochemistry:
Syntheses and Applications Pp. 317-329
Ralf Schirrmacher, Carmen Wängler and Esther Schirrmacher
[Abstract]
Recent Progress in One-Pot Syntheses of Fluorinated
Building Blocks Pp. 330-337
Xiaoming Ren, Wen Wan, Haizhen Jiang and Jian Hao
[Abstract]
Abstracts
[Back to top]
Pseudopeptide Synthesis via Fmoc
Solid-Phase Synthetic Methodology
Predrag Cudic and Maciej Stawikowski
Peptidomimetic modifications are frequently used as attractive
methods to provide more conformationally constrained and thus
more stable and bioactive peptides. Among peptidomimetic approaches,
particularly attractive are pseudopeptides, or peptide bond
surrogates in which peptide bonds have been replaced with
other chemical groups. Since these peptidomimetics can be
constructed in a modular way from orthogonally protected monomeric
building blocks, solid-phase Fmoc methodology, used routinely
for peptide synthesis, emerged as a particularly attractive
synthetic approach.
[Back to top]
Conjugation of 1,4,7,10-Tetraazacyclododecane-1,4,
7,10 Tetracetic Acid (DOTA) and its Derivatives to Peptides:
Synthesis, Applications and Future Prospects
Z. Kovacs and L. M. De León-Rodríguez
The universal chelator 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetracetic
acid (DOTA) and its bifunctional derivatives are widely used
to label peptides with various metal ions for biomedical applications.
Bifunctional DOTA derivatives and their conjugation to peptides
has become an established strategy for constructing target-specific
metal containing agents including targeted MRI contrast agents
and diagnostic and therapeutic radiopharmaceuticals. This
review covers the synthesis of DOTA-peptide conjugates, their
potential use in biomedicine and the problems related to their
applications.
[Back to top]
Supramolecular Chemistry with Phthalimide Derivatives
Nilotpal Barooah and Jubaraj B. Baruah
Recent reports on various aspects of chemistry of phthalimide
are being reviewed. The emerging development of supramolecular
aspects of phthalimide derivatives are critically analyzed
by examining the structures of host-guest complexes and also
inorganic complexes. The role of weak interactions in deciding
structures in solid states is discussed to reveal meta-stable
species involved in nucleation process.
[Back to top]
Mechanistic and Synthetic Aspects of the Benzilic
Acid and Ester Rearrangements
Anthony J. Burke and C.S. Marques
Since its discovery the Benzilic acid rearrangement has been
the subject of a number of mechanistic studies and successfully
employed in key steps in the synthesis of a number of important
target molecules. In this review we look at the advances that
have been made over the last 20 years in understanding the
mechanism of this rearrangement (including the stereochemical
aspects), whilst reviewing some important syntheses where
this particular rearrangement was used as a key step.
[Back to top]
Recent Developments and Trends in 18F-Radiochemistry:
Syntheses and Applications
Ralf Schirrmacher, Carmen Wängler and Esther Schirrmacher
In this short review we describe recent methods and novel
trends for the introduction of fluorine-18 into molecules
which in turn are intended to serve as imaging agents for
the in vivo imaging modality positron emission tomography
(PET). These 18F-labeling
schemes are based on enzymatic fluorination, the use of ionic
liquids, protic solvents acting as catalysts, application
of “click chemistry”, thiol-reactive labeling
agents for peptide and protein labeling and the most recent
introduction of “non-classical” radiochemistry
based on organo-phosphorous, organo-boron and organo-silicon
radiochemistry. The latter approach for the first time introduced
an 18F-chemistry characterized
by high selectivity and unique efficiency making complicated
work-up procedures obsolete.
[Back to top]
Recent Progress in One-Pot Syntheses of Fluorinated
Building Blocks
Xiaoming Ren, Wen Wan, Haizhen Jiang and Jian Hao
Fluorine-containing molecules are now widely selected for
both fundamental research and industrial applications in the
fields of pharmaceuticals, agrochemicals, and advanced materials.
The development of methodologies for the efficient synthesis
of fluorine-containing molecules has become one of the most
important issues in organic chemistry for long time. This
mini-review focuses on the recent development in the one-pot
syntheses of some important fluorinated building blocks which
are recognized as the versatile tools for the construction
of fluorine-containing molecules.
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