Featured Research

from universities, journals, and other organizations

New set of building blocks for simple synthesis of complex molecules

Date:
August 23, 2011
Source:
University of Illinois at Urbana-Champaign
Summary:
Assembling chemicals can be like putting together a puzzle. Chemists have developed a way of fitting the pieces together to more efficiently build complex molecules, beginning with a powerful and promising antioxidant.

Graduate student Seiko Fujii and chemistry professor Martin Burke developed a novel class of chemical "building blocks" to more efficiently synthesize complex molecules, such as the antioxidant synechoxanthin.
Credit: Becky Duffield

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.


Story Source:

The above story is based on materials provided by University of Illinois at Urbana-Champaign. Note: Materials may be edited for content and length.


Journal Reference:

  1. Seiko Fujii, Stephanie Y. Chang, Martin D. Burke. Total Synthesis of Synechoxanthin through Iterative Cross-Coupling. Angewandte Chemie International Edition, 2011; 50 (34): 7862 DOI: 10.1002/anie.201102688

Cite This Page:

University of Illinois at Urbana-Champaign. "New set of building blocks for simple synthesis of complex molecules." ScienceDaily. ScienceDaily, 23 August 2011. <www.sciencedaily.com/releases/2011/08/110823165350.htm>.
University of Illinois at Urbana-Champaign. (2011, August 23). New set of building blocks for simple synthesis of complex molecules. ScienceDaily. Retrieved August 20, 2014 from www.sciencedaily.com/releases/2011/08/110823165350.htm
University of Illinois at Urbana-Champaign. "New set of building blocks for simple synthesis of complex molecules." ScienceDaily. www.sciencedaily.com/releases/2011/08/110823165350.htm (accessed August 20, 2014).

Share This




More Matter & Energy News

Wednesday, August 20, 2014

Featured Research

from universities, journals, and other organizations


Featured Videos

from AP, Reuters, AFP, and other news services

Awesome New Camouflage Sheet Was Inspired By Octopus Skin

Awesome New Camouflage Sheet Was Inspired By Octopus Skin

Newsy (Aug. 19, 2014) Scientists have developed a new device that mimics the way octopuses blend in with their surroundings to hide from dangerous predators. Video provided by Newsy
Powered by NewsLook.com
Researcher Testing on-Field Concussion Scanners

Researcher Testing on-Field Concussion Scanners

AP (Aug. 19, 2014) Four Texas high school football programs are trying out an experimental system designed to diagnose concussions on the field. The technology is in response to growing concern over head trauma in America's most watched sport. (Aug. 19) Video provided by AP
Powered by NewsLook.com
Green Power Blooms as Japan Unveils 'hydrangea Solar Cell'

Green Power Blooms as Japan Unveils 'hydrangea Solar Cell'

AFP (Aug. 19, 2014) A solar cell that resembles a flower is offering a new take on green energy in Japan, where one scientist is searching for renewables that look good. Duration: 01:29 Video provided by AFP
Powered by NewsLook.com
Tiny Satellites, Like The One Tossed From ISS, On The Rise

Tiny Satellites, Like The One Tossed From ISS, On The Rise

Newsy (Aug. 18, 2014) The Chasqui I, hand-delivered into orbit by a Russian cosmonaut, is one of hundreds of small satellites set to go up in the next few years. Video provided by Newsy
Powered by NewsLook.com

Search ScienceDaily

Number of stories in archives: 140,361

Find with keyword(s):
Enter a keyword or phrase to search ScienceDaily for related topics and research stories.

Save/Print:
Share:

Breaking News:
from the past week

In Other News

... from NewsDaily.com

Science News

Health News

Environment News

Technology News



Save/Print:
Share:

Free Subscriptions


Get the latest science news with ScienceDaily's free email newsletters, updated daily and weekly. Or view hourly updated newsfeeds in your RSS reader:

Get Social & Mobile


Keep up to date with the latest news from ScienceDaily via social networks and mobile apps:

Have Feedback?


Tell us what you think of ScienceDaily -- we welcome both positive and negative comments. Have any problems using the site? Questions?
Mobile: iPhone Android Web
Follow: Facebook Twitter Google+
Subscribe: RSS Feeds Email Newsletters
Latest Headlines Health & Medicine Mind & Brain Space & Time Matter & Energy Computers & Math Plants & Animals Earth & Climate Fossils & Ruins