Featured Research

from universities, journals, and other organizations

Breaking carbon-hydrogen bonds: Cheap, easy 'kitchen chemistry' developed to perform formerly complex synthesis

Date:
December 5, 2009
Source:
Scripps Research Institute
Summary:
Scientists have made major strides in solving a problem that has been plaguing chemists for many years: how best to break carbon-hydrogen bonds and then to create new bonds to join molecules together. This problem is of great interest to the pharmaceutical industry, which currently relies on a method to accomplish this feat that is relatively inefficient and sometimes difficult to perform.

A team at The Scripps Research Institute has made major strides in solving a problem that has been plaguing chemists for many years: how best to break carbon-hydrogen bonds and then to create new bonds to join molecules together. This problem is of great interest to the pharmaceutical industry, which currently relies on a method to accomplish this feat that is relatively inefficient and sometimes difficult to perform.

The research, led by Scripps Research Associate Professor Jin-Quan Yu, was published November 26, 2009, in Science Express, an advance, online edition of the journal Science.

"This paper is a big jump forward," said Yu. "Our reaction is as simple as something you'd do in the kitchen. There are many fewer steps than the conventional method. There's less waste. In addition, everything you need is inexpensive and off-the-shelf -- including common table salt."

Because carbon-hydrogen bonds are simple and abundant in naturally occurring organic molecules and in commercially available drugs, they are ideal targets for chemists who want to design and manipulate molecules. An improvement to current methods for working with these bonds has the potential to revolutionize work done in academic and industrial laboratories around the world.

Bread-and-Butter Technology

Currently, to forge carbon-carbon bonds in place of carbon-hydrogen bonds, chemists rely heavily on a method called "Mizoroki-Heck reaction."

In this reaction, chemists first must install a halide in the molecule of interest as a "handle," replacing the existing carbon-hydrogen bonds with carbon-halide bonds. The chemists then join these molecules with other molecules using a metal catalyst, and then remove the "halide handle."

"Once installed, the halide can stick like glue," explained Yu, "so you can join one halogenated molecule with another molecule readily with a metal catalyst. The halide technique is very powerful and many technologies use it, including for the creation of almost any drug. It's a bread-and-butter technology."

But, despite its widespread use, this technique has some downsides. First, there's the waste (both in terms of labor and energy as well as literal waste) of the steps of adding and removing the halide from the molecules. Then, perhaps even more problematic, installing the halide into a molecule of interest isn't always so easy.

"To install a halide, you have to install it at the right position," said Yu. "You can't install it just anywhere. Sometimes that is impossible or difficult, taking many, many steps."

So the question arose: Can chemists develop a new method to manipulate carbon-hydrogen bonds and join together molecules without the intermediate step of installing a halide?

The Search for a Better Way

Over the last several years, many laboratories around the world have taken up this challenge. Early research in this new area of study (including papers by Yu) showed that this goal was possible to achieve under specialized conditions. However, making the reaction economically feasible and practical for the average chemistry laboratory was an elusive goal -- until now.

In the new Science Express paper, Yu and colleagues start with a simple and commonly used substrate, a derivative of acetic acid (which gives vinegar it's sour taste).

"This substrate is used daily in the pharmaceutical industry and in natural product synthesis," said Yu. "It's a major class."

The team then designed ligands (molecules that bind to a site on a metal catalyst) out of simple derivatives of amino acids (protein building blocks). Because of their specific shape, these ligands guide the metal to break a carbon-hydrogen bond at a particular position selectively, and carbon-carbon bond formation with another molecule then takes place.

To demonstrate the utility and versatility of the lab's technique, for the study the team synthesized several natural product core structures. These included a complex molecule, a polyketide aromatic, that is an essential component of many antibiotics.

"The Science paper is the first demonstration that we can actually take an acetic acid derivative and then make a very complex molecule," said Yu. "And yet in none of the steps do we use anything the layman cannot afford or take off the shelf. We call it 'layman chemistry.' We expect that this reaction and others grounded in this philosophy will find many uses."

In addition to Yu, who is a recent recipient of the Eli Lilly Grantee Award, authors of the paper are graduate students Dong-Hui Wang and Keary Engle, and postdoctoral fellow Bing-Feng Shi, all of Scripps Research.

The research was supported by Scripps Research, the National Institutes of Health, Amgen, and Eli Lilly, as well as by fellowships from the A.P. Sloan Foundation, the National Science Foundation, the Department of Defense, Scripps Research, and the Skaggs Oxford Scholarship Program.



Story Source:

The above story is based on materials provided by Scripps Research Institute. Note: Materials may be edited for content and length.


Cite This Page:

Scripps Research Institute. "Breaking carbon-hydrogen bonds: Cheap, easy 'kitchen chemistry' developed to perform formerly complex synthesis." ScienceDaily. ScienceDaily, 5 December 2009. <www.sciencedaily.com/releases/2009/12/091204092521.htm>.
Scripps Research Institute. (2009, December 5). Breaking carbon-hydrogen bonds: Cheap, easy 'kitchen chemistry' developed to perform formerly complex synthesis. ScienceDaily. Retrieved August 1, 2014 from www.sciencedaily.com/releases/2009/12/091204092521.htm
Scripps Research Institute. "Breaking carbon-hydrogen bonds: Cheap, easy 'kitchen chemistry' developed to perform formerly complex synthesis." ScienceDaily. www.sciencedaily.com/releases/2009/12/091204092521.htm (accessed August 1, 2014).

Share This




More Matter & Energy News

Friday, August 1, 2014

Featured Research

from universities, journals, and other organizations


Featured Videos

from AP, Reuters, AFP, and other news services

Britain Testing Driverless Cars on Roadways

Britain Testing Driverless Cars on Roadways

AP (July 30, 2014) British officials said on Wednesday that driverless cars will be tested on roads in as many as three cities in a trial program set to begin in January. Officials said the tests will last up to three years. (July 30) Video provided by AP
Powered by NewsLook.com
7 Ways to Use Toothpaste: Howdini Hacks

7 Ways to Use Toothpaste: Howdini Hacks

Howdini (July 30, 2014) Fresh breath and clean teeth are great, but have you ever thought, "my toothpaste could be doing more". Well, it can! Lots of things! Howdini has 7 new uses for this household staple. Video provided by Howdini
Powered by NewsLook.com
Amid Drought, UCLA Sees Only Water

Amid Drought, UCLA Sees Only Water

AP (July 30, 2014) A ruptured 93-year-old water main left the UCLA campus awash in 8 million gallons of water in the middle of California's worst drought in decades. (July 30) Video provided by AP
Powered by NewsLook.com
Smartphone Powered Paper Plane Debuts at Airshow

Smartphone Powered Paper Plane Debuts at Airshow

AP (July 30, 2014) Smartphone powered paper airplane that was popular on crowdfunding website KickStarter makes its debut at Wisconsin airshow (July 30) Video provided by AP
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