Navigation Links
A new set of building blocks for simple synthesis of complex molecules
Date:8/23/2011

CHAMPAIGN, Ill. 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.


'/>"/>

Contact: Liz Ahlberg
eahlberg@illinois.edu
217-244-1073
University of Illinois at Urbana-Champaign
Source:Eurekalert  

Related medicine news :

1. Researchers building new sensor that could stop falls by elderly, before they happen
2. Building Muscle May Reduce Diabetes Risk, Study Says
3. Beef: Americas favorite protein is an essential building block
4. Key goals for building on 30 years of HIV/AIDS research
5. I can hear a building over there
6. Playing with building blocks of creativity help children with autism
7. Coming Soon: Smoke-Free Apartment Buildings?
8. With muscle-building treatment, mice live longer even as tumors grow
9. Building a bridge with cross-cultural cancer education
10. Technology for locating first responders in buildings to be showcased at national workshop
11. Scottsdale Named One of US' Greenest Cities, Green Building Permits on the Rise
Post Your Comments:
*Name:
*Comment:
*Email:
Related Image:
A new set of building blocks for simple synthesis of complex molecules
(Date:3/28/2017)... (PRWEB) , ... March 28, 2017 , ... ... leading physicians, Paul Yost, will begin serving as new board chair for Orange ... month. Yost will serve the remainder of soon-to-be former chair Mark Refowitz’s term, ...
(Date:3/28/2017)... ... March 28, 2017 , ... In its ongoing effort ... has recently developed and published an informational resource that addresses frequently asked questions. ... common inquiries the site’s team of third party administrator (TPA) contributors regularly receives ...
(Date:3/28/2017)... ... March 28, 2017 , ... Prominant bariatric surgeon ... is thrilled to offer the recently FDA-approved Obalon Balloon System to his patients. ... SkyLex Advanced Surgical’s already comprehensive list of weight-loss services. Dr. Liu is ...
(Date:3/28/2017)... ... 2017 , ... Oily skin is a common and unwelcomed occurrence in people of all ages, ... to offer to the discussion of dealing with excess skin oil. “Oily skin is a ... remedies that can help remove the oily shine while keeping the skin fresh and clean,” ...
(Date:3/27/2017)... Aurora, CO (PRWEB) , ... March 27, 2017 , ... ... Dr. Mark Braasch for leading sleep apnea treatment, with or without a referral. Sleep ... the condition, which can include daytime sleepiness, morning headaches and chronic snoring. , ...
Breaking Medicine News(10 mins):
(Date:3/28/2017)... , March 28, 2017  Akcea Therapeutics, a subsidiary ... to the company,s board of directors: ... Partners. Mr. Gabrieli will serve as chairman of the board ... former chief commercial officer of Forest Laboratories. ... Biolink Partners. "We are excited to ...
(Date:3/28/2017)... 28, 2017 RXi Pharmaceuticals Corporation (NASDAQ: ... that address significant unmet medical needs, today announced ... Japan Patent Office (JPO) for the composition of ... (CTGF) for the treatment or prevention of fibrotic ... and proliferative retinopathy (Japanese Patent #: 6060071).  This ...
(Date:3/28/2017)... , March 28, 2017  Medeon Biodesign, Inc., ... company, is pleased to announce that the Company ... of Panther Orthopedics, Inc., a San ... fixation solutions for orthopedic extremity applications.  ... expand rapidly, primarily due to procedure volume growth, ...
Breaking Medicine Technology: