Forum for Science, Industry and Business

Sponsored by:     3M 
Search our Site:

 

A new set of building blocks for simple synthesis of complex molecules

23.08.2011
Assembling chemicals can be like putting together a puzzle. University of Illinois chemists have developed a way of fitting the pieces together to more efficiently build complex molecules, beginning with a powerful and promising antioxidant.

Led by chemistry professor Martin Burke, the team published its research on the cover of the chemistry journal Angewandte Chemie.

Burke’s group is known for developing a synthesis technique called iterative cross-coupling (ICC) that uses simple, stable chemical “building blocks” sequentially joined in a repetitive reaction. With more than 75 of the building blocks available commercially, pharmaceutical companies and other laboratories use ICC to create complex small molecules that could have medicinal properties.

“There’s pre-installed functionality and stereochemistry, so everything is set in the building blocks, and all you have to do is couple them together,” said graduate student Seiko Fujii, the first author of the paper.

However, ICC has been limited to only molecules with one type of polarity. Now, the group has developed reverse-polarity ICC, which allows a chemist to optimize the ICC process to match the target molecules’ electronic structure. The reversal in polarity enables a whole new class of building blocks, so researchers can synthesize molecules more efficiently and even construct molecules that standard ICC cannot.

For example, in the paper, the group used the new method to make synechoxanthin (pronounced sin-ecko-ZAN-thin), a molecule first isolated from bacteria in 2008 that shows great promise as an antioxidant. Studies suggest that synechoxanthin allows the bacteria that produce it to live and thrive in highly oxidative environments.

“We as humans experience a lot of oxidative stress, and it can be really deleterious to human health,” said Burke, who also is affiliated with the Howard Hughes Medical Institute. “It can lead to diseases like cancer and atherosclerosis and neurodegenerative disorders. Evidence strongly suggests that synechoxanthin is a major part of the bacteria’s solution to this problem. We’re excited to ask the question, what can we learn from the bug? Can it also protect a human cell?”

Studies on the activity of synechoxanthin have been limited by the difficulty of extracting the molecule from bacterial cultures. Burke’s group successfully synthesized it from a mere three types of readily available, highly stable, non-toxic building blocks. Thanks to the ease of ICC, they can produce relatively large quantities of synechoxanthin for study as well as derivatives to test against the natural product.

“Because this building-block-based design is inherently flexible, once we’ve made the natural product, we can make any derivative we want simply by swapping in one different building block, and then using the reverse-polarity ICC to snap them together,” Burke said. “That’s where synthesis is so powerful. Oftentimes, the cleanest experiment will require a molecule that doesn’t exist, unless you can piece it together.”

Researchers can also use blocks that have been “tagged” with a fluorescent or radioactive dye to make it easier to study the molecule and its activity. For example, Fujii next plans to synthesize both synechoxanthin and its apolar derivative with tags so that NMR imaging can reveal its location and orientation within a cell’s membrane, possibly providing clues to its activity.
“After we have all these molecules in hand, we’re really excited to test the antioxidant activity of them in a model membrane,” Fujii said.

The National Institutes of Health and the Howard Hughes Medical Institute supported this work.

Editor’s notes: To reach Martin Burke, call 217-244-8726; email burke@scs.illinois.edu.

The paper, “Total Synthesis of Synechoxanthin through Iterative Cross-Coupling,” is available online

Liz Ahlberg | University of Illinois
Further information:
http://www.illinois.edu

More articles from Life Sciences:

nachricht Transport of molecular motors into cilia
28.03.2017 | Aarhus University

nachricht Asian dust providing key nutrients for California's giant sequoias
28.03.2017 | University of California - Riverside

All articles from Life Sciences >>>

The most recent press releases about innovation >>>

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

Im Focus: A Challenging European Research Project to Develop New Tiny Microscopes

The Institute of Semiconductor Technology and the Institute of Physical and Theoretical Chemistry, both members of the Laboratory for Emerging Nanometrology (LENA), at Technische Universität Braunschweig are partners in a new European research project entitled ChipScope, which aims to develop a completely new and extremely small optical microscope capable of observing the interior of living cells in real time. A consortium of 7 partners from 5 countries will tackle this issue with very ambitious objectives during a four-year research program.

To demonstrate the usefulness of this new scientific tool, at the end of the project the developed chip-sized microscope will be used to observe in real-time...

Im Focus: Giant Magnetic Fields in the Universe

Astronomers from Bonn and Tautenburg in Thuringia (Germany) used the 100-m radio telescope at Effelsberg to observe several galaxy clusters. At the edges of these large accumulations of dark matter, stellar systems (galaxies), hot gas, and charged particles, they found magnetic fields that are exceptionally ordered over distances of many million light years. This makes them the most extended magnetic fields in the universe known so far.

The results will be published on March 22 in the journal „Astronomy & Astrophysics“.

Galaxy clusters are the largest gravitationally bound structures in the universe. With a typical extent of about 10 million light years, i.e. 100 times the...

Im Focus: Tracing down linear ubiquitination

Researchers at the Goethe University Frankfurt, together with partners from the University of Tübingen in Germany and Queen Mary University as well as Francis Crick Institute from London (UK) have developed a novel technology to decipher the secret ubiquitin code.

Ubiquitin is a small protein that can be linked to other cellular proteins, thereby controlling and modulating their functions. The attachment occurs in many...

Im Focus: Perovskite edges can be tuned for optoelectronic performance

Layered 2D material improves efficiency for solar cells and LEDs

In the eternal search for next generation high-efficiency solar cells and LEDs, scientists at Los Alamos National Laboratory and their partners are creating...

Im Focus: Polymer-coated silicon nanosheets as alternative to graphene: A perfect team for nanoelectronics

Silicon nanosheets are thin, two-dimensional layers with exceptional optoelectronic properties very similar to those of graphene. Albeit, the nanosheets are less stable. Now researchers at the Technical University of Munich (TUM) have, for the first time ever, produced a composite material combining silicon nanosheets and a polymer that is both UV-resistant and easy to process. This brings the scientists a significant step closer to industrial applications like flexible displays and photosensors.

Silicon nanosheets are thin, two-dimensional layers with exceptional optoelectronic properties very similar to those of graphene. Albeit, the nanosheets are...

All Focus news of the innovation-report >>>

Anzeige

Anzeige

Event News

International Land Use Symposium ILUS 2017: Call for Abstracts and Registration open

20.03.2017 | Event News

CONNECT 2017: International congress on connective tissue

14.03.2017 | Event News

ICTM Conference: Turbine Construction between Big Data and Additive Manufacturing

07.03.2017 | Event News

 
Latest News

Researchers shoot for success with simulations of laser pulse-material interactions

29.03.2017 | Materials Sciences

Igniting a solar flare in the corona with lower-atmosphere kindling

29.03.2017 | Physics and Astronomy

As sea level rises, much of Honolulu and Waikiki vulnerable to groundwater inundation

29.03.2017 | Earth Sciences

VideoLinks
B2B-VideoLinks
More VideoLinks >>>