Forum for Science, Industry and Business

Sponsored by:     3M 
Search our Site:

 

Eclectic Enzymes

02.09.2010
Easily Modified Building Blocks for Drug Design

In the pursuit of biologically active compounds, it is often necessary to be able to control the stereochemistry at predefined positions in a molecular skeleton. The search for ways to prepare chiral building blocks with known configuration that also show structural differentiation is important.

Italian scientists working with Elisabetta Brenna have developed a technique to separate individual stereoisomers of building blocks that can be easily integrated into biologically active molecules. As the scientists from Politecnico di Milano, Milano, Italy, report in the European Journal of Organic Chemistry, their technique relies on the use of enzymes.

The specific activity of a biologically relevant molecule is often dependent on its stereochemistry (i.e., the spatial arrangement of its atoms). However, most compounds showing biological activity have complex structures, making their synthesis difficult. Moreover, compounds with differing stereochemistries can show different activities. Thus, it is sometimes desirable to prepare a range of compounds with the same structural backbone, but having different spatial arrangements of their atoms. The use of configurationally defined building blocks is attractive, but a method to obtain all the stereoisomers of a given building block is thus required.

Brenna and her colleagues have developed a method that allows a mixture of isomers to be differentiated, and it depends on the use of the enzyme lipase PS. The resolution of the stereoisomers relies on the preferential reaction of the enzyme with only one isomer, thereby creating a product mixture containing the desired compound and a mixture of the unreacted isomers. The desired product can be easily separated from the unreacted mixture, which can then be resubjected to the enzyme to undergo further differentiation. In this way, a wide range of building blocks with differing and known stereochemistries can be prepared.

The authors then showed the applicability of their method by incorporating their configurationally defined building blocks into biologically active compounds. Using simple and straightforward organic chemistry transformations, the authors were able to embed their building blocks into two classes of compounds that are of biological interest. Importantly, scientists can now easily examine the biological activities of all the different stereoisomers of a given compound. Thus, the Italian team is well on their way to helping scientists screen a diverse range of potential drugs that may lead to the treatment, cure, prevention, or diagnosis of diseases.

Author: Elisabetta Brenna, Politecnico di Milano (Italy), http://www.chem.polimi.it/people/faculty/elisabetta-brenna/

Title: Oxygenated Stereotriads with Definite Absolute Configuration by Lipase-Mediated Kinetic Resolution: De Novo Synthesis of Imino Sugars and 6-Deoxy-C-glycosides

European Journal of Organic Chemistry , 2010, No. 23, 4468–4475, Permalink to the article: http://dx.doi.org/10.1002/ejoc.201000558

Elisabetta Brenna | Wiley-VCH
Further information:
http://www.wiley-vch.de
http://www.chem.polimi.it/people/faculty/elisabetta-brenna/

More articles from Life Sciences:

nachricht The dense vessel network regulates formation of thrombocytes in the bone marrow
25.07.2017 | Rudolf-Virchow-Zentrum für Experimentelle Biomedizin der Universität Würzburg

nachricht Fungi that evolved to eat wood offer new biomass conversion tool
25.07.2017 | University of Massachusetts at Amherst

All articles from Life Sciences >>>

The most recent press releases about innovation >>>

Die letzten 5 Focus-News des innovations-reports im Überblick:

Im Focus: Carbon Nanotubes Turn Electrical Current into Light-emitting Quasi-particles

Strong light-matter coupling in these semiconducting tubes may hold the key to electrically pumped lasers

Light-matter quasi-particles can be generated electrically in semiconducting carbon nanotubes. Material scientists and physicists from Heidelberg University...

Im Focus: Flexible proximity sensor creates smart surfaces

Fraunhofer IPA has developed a proximity sensor made from silicone and carbon nanotubes (CNT) which detects objects and determines their position. The materials and printing process used mean that the sensor is extremely flexible, economical and can be used for large surfaces. Industry and research partners can use and further develop this innovation straight away.

At first glance, the proximity sensor appears to be nothing special: a thin, elastic layer of silicone onto which black square surfaces are printed, but these...

Im Focus: 3-D scanning with water

3-D shape acquisition using water displacement as the shape sensor for the reconstruction of complex objects

A global team of computer scientists and engineers have developed an innovative technique that more completely reconstructs challenging 3D objects. An ancient...

Im Focus: Manipulating Electron Spins Without Loss of Information

Physicists have developed a new technique that uses electrical voltages to control the electron spin on a chip. The newly-developed method provides protection from spin decay, meaning that the contained information can be maintained and transmitted over comparatively large distances, as has been demonstrated by a team from the University of Basel’s Department of Physics and the Swiss Nanoscience Institute. The results have been published in Physical Review X.

For several years, researchers have been trying to use the spin of an electron to store and transmit information. The spin of each electron is always coupled...

Im Focus: The proton precisely weighted

What is the mass of a proton? Scientists from Germany and Japan successfully did an important step towards the most exact knowledge of this fundamental constant. By means of precision measurements on a single proton, they could improve the precision by a factor of three and also correct the existing value.

To determine the mass of a single proton still more accurate – a group of physicists led by Klaus Blaum and Sven Sturm of the Max Planck Institute for Nuclear...

All Focus news of the innovation-report >>>

Anzeige

Anzeige

Event News

Closing the Sustainability Circle: Protection of Food with Biobased Materials

21.07.2017 | Event News

»We are bringing Additive Manufacturing to SMEs«

19.07.2017 | Event News

The technology with a feel for feelings

12.07.2017 | Event News

 
Latest News

NASA mission surfs through waves in space to understand space weather

25.07.2017 | Physics and Astronomy

Strength of tectonic plates may explain shape of the Tibetan Plateau, study finds

25.07.2017 | Earth Sciences

The dense vessel network regulates formation of thrombocytes in the bone marrow

25.07.2017 | Life Sciences

VideoLinks
B2B-VideoLinks
More VideoLinks >>>