Navigation Links
Caltech chemists devise chemical reaction that holds promise for new drug development
Date:1/11/2012

PASADENA, Calif. -- A team of researchers at the California Institute of Technology (Caltech) has devised a new method for making complex molecules. The reaction they have come up with should enable chemists to synthesize new varieties of a whole subclass of organic compounds called nitrogen-containing heterocycles, thus opening up new avenues for the development of novel pharmaceuticals and natural products ranging from chemotherapeutic compounds to bioactive plant materials such as morphine.

The teamled by Brian Stoltz, the Ethel Wilson Bowles and Robert Bowles Professor of Chemistry, and Doug Behenna, a scientific researcherused a suite of specialized robotic tools in the Caltech Center for Catalysis and Chemical Synthesis to find the optimal conditions and an appropriate catalyst to drive this particular type of reaction, known as an alkylation, because it adds an alkyl group (a group of carbon and hydrogen atoms) to the compound. The researchers describe the reaction in a recent advance online publication of a paper in Nature Chemistry.

"We think it's going to be a highly enabling reaction, not only for preparing complex natural products, but also for making pharmaceutical substances that include components that were previously very challenging to make," Stoltz says. "This has suddenly made them quite easy to make, and it should allow medicinal chemists to access levels of complexity they couldn't previously access."

The reaction creates compounds called heterocycles, which involve cyclic groups of carbon and nitrogen atoms. Such nitrogen-containing heterocycles are found in many natural products and pharmaceuticals, as well as in many synthetic polymers. In addition, the reaction manages to form carbon-carbon bonds at sites where some of the carbon atoms are essentially hidden, or blocked, by larger nearby components.

"Making carbon-carbon bonds is hard, but that's what we need to make the complicated structures we're after," Stoltz says. "We're taking that up another notch by making carbon-carbon bonds in really challenging scenarios. We're making carbon centers that have four other carbon groups around them, and that's very hard to do."

The vast majority of pharmaceuticals being made today do not include such congested carbon centers, Stoltz saysnot so much because they would not be effective compounds, but because they have been so difficult to make. "But now," he says, "we've made it very easy to make those very hindered centers, even in compounds that contain nitrogen. And that should give pharmaceutical companies new possibilities that they previously couldn't consider."

Perhaps the most important feature of the reaction is that it yields almost 100 percent of just one version of its product. This is significant because many organic compounds exist in two distinct versions, or enantiomers, each having the same chemical formula and bond structure as the other, but with functional groups in opposite positions in space, making them mirror images of each other. One version can be thought of as right-handed, the other as left-handed.

The problem is that there is often a lock-and-key interaction between our bodies and the compounds that act upon themonly one of the two possible hands of a compound can "shake hands" and fit appropriately. In fact, one version will often have a beneficial effect on the body while the other will have a completely different and sometimes detrimental effect. Therefore, it is important to be able to selectively produce the compound with the desired handedness. For this reason, the FDA has increasingly required that the molecules in a particular drug be present in just one form.

"So not only are we making tricky carbon-carbon bonds, we're also making them such that the resulting products have a particular, desired handedness," Stoltz says. "This was the culmination of six years of work. There was essentially no way to make these compounds before, so to all of a sudden be able to do it and with perfect selectivity that's pretty awesome."


'/>"/>
Contact: Deborah Williams-Hedges
debwms@caltech.edu
626-395-3227
California Institute of Technology
Source:Eurekalert  

Related medicine news :

1. Caltech research helps paraplegic man stand and move legs voluntarily
2. Caltech biologists discover microRNAs that control function of blood stem cells
3. Caltech scientists uncover structure of key protein in common HIV subgroup
4. Rice chemists cram 2 million nanorods into single cancer cell
5. UF medicinal chemists modify sea bacteria byproduct for use as potential cancer drug
6. Breathing easy: LSU biochemists offer first 3-D model of asthma-causing inflammation enzyme
7. MIT chemists engineer plants to produce new drugs
8. Scientists devise targeted therapy strategy for rare form of childhood cancer
9. New drug screening identifies chemical agents with potent anti-cancer activity
10. UM researcher develops new way to assess risk for chemicals
11. Elsevier and Federation of Biochemical Societies launch new journal
Post Your Comments:
*Name:
*Comment:
*Email:
Related Image:
Caltech chemists devise chemical reaction that holds promise for new drug development
(Date:3/24/2017)... ... March 24, 2017 , ... Judy Buchanan, co-owner of Serenity ... MD. Judy says, “I am passionate about sharing Reiki as a holistic, complementary ... and challenging time.” , A Certified Medical Reiki™ Master trained by Raven Keys ...
(Date:3/24/2017)... ... , ... “Vintage and Harvest A Cultivation of Christian Love” is the creation ... North Carolina with his wife, Anna Marie. He and his wife are the proud ... also the author of “Shadow and Substance.” , “Love, the agape kind, is seen ...
(Date:3/23/2017)... (PRWEB) , ... March 23, 2017 , ... In 2016 ... now estimates that there could be four million Zika-related cases in the Americas within ... with numbers of US cases reported per year skyrocketing to an estimated 329,000. Yet, ...
(Date:3/23/2017)... ... March 23, 2017 , ... ... to their communities, 16 more public health departments have been awarded national accreditation ... another 4.5 million people into the expanding network of communities across the nation ...
(Date:3/23/2017)... (PRWEB) , ... March 23, 2017 , ... The IoT ... and WiFi connectivity are making a huge impact on businesses and individual consumers alike. ... estimates the IoT will have a value anywhere from $4 trillion to $11 trillion ...
Breaking Medicine News(10 mins):
(Date:3/24/2017)... 23, 2017  HealthMine surveys with 9,250 insured consumers ... health plan members want help from their plans in ... in their health, 2) help closing gaps in care, ... health and 5) relevant, real-time guidance. Meeting these needs ... costs. A Reason to Stay ...
(Date:3/23/2017)... Research and Markets has announced the addition of the "Global ... report to their offering. ... The Global Cryostat Market is poised to grow at ... approximately $3.5 billion by 2025. This industry report analyzes ... global as well as regional levels presented in the research scope. ...
(Date:3/23/2017)... LONDON , March 23, 2017 ... comprehensive research report created through extensive primary research ... research, the report aims to present the analysis ... basis of Procedure (Replacement and Repair); Replacement Procedure ... (TAVR)), Repair By Technique (Surgical Devices, Balloon Valvuloplasty, ...
Breaking Medicine Technology: