Forum for Science, Industry and Business

Sponsored by:     3M 
Search our Site:

 

Drug manufacture: Going green with iron

01.02.2013
Safe and inexpensive iron catalysts provide a ‘greener’ alternative to typical pharmaceutical production methods

More than one-quarter of all known pharmaceuticals contain the chemical group known as amides: carboxylic acid derivatives derived from ammonia or amines. Most methods for synthesizing amides, however, are inefficient and use hazardous reagents.

New work from Anqi Chen and co-workers at the A*STAR Institute of Chemical and Engineering Sciences in Singapore promises to make amide chemistry more economical and sustainable than before1. The team has uncovered a way to convert aldehydes and amine salts into amides using iron(II) sulfate - a harmless, inexpensive substance as the catalyst to perform this transformation efficiently and with little waste.

Most alternative methods to produce amide molecules use expensive noble metal catalysts such as palladium and ruthenium, which are incompatible with industrial demands for cost-efficiency. Funded by a GlaxoSmithKline (GSK)–Singapore Economic Development Board (EDB) endowment on sustainable drug manufacturing, the researchers investigated a different approach known as ‘direct oxidative amidation’. This method couples an aldehyde and an amine salt in the presence of a catalyst and an oxidant, generating an amide in one step.

Nontoxic and cheap catalysts with sufficient chemical activity for amide transformation are hard to find. To identify an efficient and inexpensive catalyst, the team screened a range of iron compounds and discovered that iron(II) sulfate (see image), a supplement for anemia that costs less than a dollar per kilogram, has strong potential to catalyze amide formation from aldehydes with amine salts.

Apart from the environmentally benign iron catalyst, the transformation uses an inexpensive oxidant known as tert-butyl hydroperoxide and very cheap calcium carbonate, the main composition of limestone, as a base. By combining these inexpensive ingredients together, the researchers achieved excellent amide yields under conditions convenient for both laboratory and industrial operations.
Further experiments revealed the versatility of this amide synthesis. A range of amine salts and aldehydes with different structural and electronic features could be transformed into amides with good-to-excellent yields. Importantly, salts derived from natural amino acids such as valine and proline also underwent oxidative amidation without disrupting their chirality or ‘handedness’ - a critical structural phenomenon for drug molecules and peptides.

The team demonstrated the potential of this iron-catalyzed amidation for drug manufacturing by synthesizing the antiarrhythmic drug N-acetylprocainamide in a one-step procedure that is more efficient than previous multiple-step routes. “This environmentally benign method has significant advantages over conventional techniques,” says Chen, “and we intend to identify pharmaceutical targets where this promising method could bring about significant cost-savings and improved sustainability.”

The A*STAR-affiliated researchers contributing to this research are from the Institute of Chemical and Engineering Sciences

Journal information
Ghosh, S. C., Ngiam, J. S. Y., Chai, C. L. L., Seayad, A. M., Dang, T. T. & Chen, A. Iron-catalyzed efficient synthesis of amides from aldehydes and amine hydrochloride salts. Advanced Synthesis & Catalysis 354, 1407–1412 (2012).

A*STAR Research | Research asia research news
Further information:
http://www.a-star.edu.sg
http://www.researchsea.com

More articles from Life Sciences:

nachricht Fish Oil-Diet Benefits May be Mediated by Gut Microbes
28.08.2015 | University of Gothenburg

nachricht Bio-fabrication of Artificial Blood Vessels with Laser Light
28.08.2015 | Fraunhofer-Institut für Lasertechnik ILT

All articles from Life Sciences >>>

The most recent press releases about innovation >>>

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

Im Focus: OU astrophysicist and collaborators find supermassive black holes in quasar nearest Earth

A University of Oklahoma astrophysicist and his Chinese collaborator have found two supermassive black holes in Markarian 231, the nearest quasar to Earth, using observations from NASA's Hubble Space Telescope.

The discovery of two supermassive black holes--one larger one and a second, smaller one--are evidence of a binary black hole and suggests that supermassive...

Im Focus: What would a tsunami in the Mediterranean look like?

A team of European researchers have developed a model to simulate the impact of tsunamis generated by earthquakes and applied it to the Eastern Mediterranean. The results show how tsunami waves could hit and inundate coastal areas in southern Italy and Greece. The study is published today (27 August) in Ocean Science, an open access journal of the European Geosciences Union (EGU).

Though not as frequent as in the Pacific and Indian oceans, tsunamis also occur in the Mediterranean, mainly due to earthquakes generated when the African...

Im Focus: Self-healing landscape: landslides after earthquake

In mountainous regions earthquakes often cause strong landslides, which can be exacerbated by heavy rain. However, after an initial increase, the frequency of these mass wasting events, often enormous and dangerous, declines, in fact independently of meteorological events and aftershocks.

These new findings are presented by a German-Franco-Japanese team of geoscientists in the current issue of the journal Geology, under the lead of the GFZ...

Im Focus: FIC Proteins Send Bacteria Into Hibernation

Bacteria do not cease to amaze us with their survival strategies. A research team from the University of Basel's Biozentrum has now discovered how bacteria enter a sleep mode using a so-called FIC toxin. In the current issue of “Cell Reports”, the scientists describe the mechanism of action and also explain why their discovery provides new insights into the evolution of pathogens.

For many poisons there are antidotes which neutralize their toxic effect. Toxin-antitoxin systems in bacteria work in a similar manner: As long as a cell...

Im Focus: Fraunhofer IPA develops prototype of intelligent care cart

It comes when called, bringing care utensils with it and recording how they are used: Fraunhofer IPA is developing an intelligent care cart that provides care staff with physical and informational support in their day-to-day work. The scientists at Fraunhofer IPA have now completed a first prototype. In doing so, they are continuing in their efforts to improve working conditions in the care sector and are developing solutions designed to address the challenges of demographic change.

Technical assistance systems can improve the difficult working conditions in residential nursing homes and hospitals by helping the staff in their work and...

All Focus news of the innovation-report >>>

Anzeige

Anzeige

Event News

Networking conference in Heidelberg for outstanding mathematicians and computer scientists

20.08.2015 | Event News

Scientists meet in Münster for the world’s largest Chitin und Chitosan Conference

20.08.2015 | Event News

Large agribusiness management strategies

19.08.2015 | Event News

 
Latest News

Interstellar seeds could create oases of life

28.08.2015 | Physics and Astronomy

An ounce of prevention: Research advances on 'scourge' of transplant wards

28.08.2015 | Health and Medicine

Fish Oil-Diet Benefits May be Mediated by Gut Microbes

28.08.2015 | Life Sciences

VideoLinks
B2B-VideoLinks
More VideoLinks >>>