Forum for Science, Industry and Business

Sponsored by:     3M 
Search our Site:

 

Breakthrough Improves Method for Synthesizing Cyanohydrins as Pharmaceutical Precursors

24.02.2016

A research group led by Dr. Kazuaki Ishihara, a professor at Nagoya University, has established a new method of chemically modifying ketones in a way that ensures that optically active cyanohydrins are obtained, enabling efficient production of pharmaceutical precursors at a high yield and with good selectivity.

In the production of pharmaceuticals, it is extremely important to produce molecules that have the right kind of symmetry. Even products that have the same composition, but are mirror images of each other, can have different effects in the body.


A cyano group is added to a ketone using a chiral lithium(I) catalyst system to achieve control over the symmetry of the resulting pharmaceutical cyanohydrins.

Copyright : Nagoya University

Considerable interest has been generated by a recent advance made by scientists at Nagoya University, which was reported online in the journal Angewandte Chemie. Specifically, these researchers managed to modify molecules called ketones by adding new chemical groups in a way that produces more of a single mirror image of the same type of molecule.

This study extends previous work on modifying ketones to produce cyanohydrins, which are useful molecules because they are precursors of carboxylic acids and some amino acids, which are the building blocks of life. The similarity of cyanohydrins and their derivatives to amino acids means that they have important pharmaceutical properties.

However, in previous studies, the modification of ketones to produce cyanohydrins was inefficient, time-consuming, could only produce a small amount of desired product, and was only available for a narrow range of compounds.

These obstacles have now been overcome by an innovative new reaction. “Using a new catalyst, chiral lithium(I) phosphoryl phenoxide, we have been able to add a cyano group with excellent enantioselectivity on ketones using lithium dicyanotrimethylsilicate(IV),” says Dr. Manabu Hatano, an associate professor and the first author. “This reaction had a high yield despite only a weak Lewis acid catalyst being used.”

Previous studies in which efforts were made to produce optically active cyanohydrins encountered difficulties when using ketones rather than aldehydes as the molecules to be cyanosilylated because they are less reactive. This was overcome by the new approach, which was demonstrated by synthesizing a key intermediate for the production of (+)-13-hydroxyisocyclocelabenzine, a pharmaceutical that has antibacterial and antitumor effects.

“Another advantage of our new method is that the reaction time is much shorter, lasting only 2 to 9 hours rather than 1 to 2 days,” according to Katsuya Yamakawa, another member of the research team. “This would be helpful in the pharmaceutical industry when attempting to produce the desired products on a large scale for medical use.”

After the demonstration of this new catalytic system in a large-scale reaction, it is hoped that it can be applied widely for more effective cyanosilylation, enabling cheaper and more accurate production of pharmaceutical products.

The article “Enantioselective Cyanosilylation of Ketones with Lithium(I) Dicyanotrimethylsilicate(IV) Catalyzed by a Chiral Lithium(I) Phosphoryl Phenoxide” was published online in Angewandte Chemie, at doi: 10.1002/anie.201510682


Journal information

Angewandte Chemie, at doi: 10.1002/anie.201510682

Koomi Sung | Research SEA
Further information:
http://en.nagoya-u.ac.jp/index.html
http://www.researchsea.com

More articles from Life Sciences:

nachricht Faster detection of pathogens in the lungs
24.06.2016 | Universität Zürich

nachricht How yeast cells regulate their fat balance
23.06.2016 | Goethe-Universität Frankfurt am Main

All articles from Life Sciences >>>

The most recent press releases about innovation >>>

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

Im Focus: First experimental quantum simulation of particle physics phenomena

Physicists in Innsbruck have realized the first quantum simulation of lattice gauge theories, building a bridge between high-energy theory and atomic physics. In the journal Nature, Rainer Blatt‘s and Peter Zoller’s research teams describe how they simulated the creation of elementary particle pairs out of the vacuum by using a quantum computer.

Elementary particles are the fundamental buildings blocks of matter, and their properties are described by the Standard Model of particle physics. The...

Im Focus: Is There Life On Mars?

Survivalist back from Space - 18 months on the outer skin of the ISS

A year and a half on the outer wall of the International Space Station ISS in altitude of 400 kilometers is a real challenge. Whether a primordial bacterium...

Im Focus: CWRU physicists deploy magnetic vortex to control electron spin

Potential technology for quantum computing, keener sensors

Researchers at Case Western Reserve University have developed a way to swiftly and precisely control electron spins at room temperature.

Im Focus: Physicists measured something new in the radioactive decay of neutrons

The experiment inspired theorists; future ones could reveal new physics

A physics experiment performed at the National Institute of Standards and Technology (NIST) has enhanced scientists' understanding of how free neutrons decay...

Im Focus: Discovery of gold nanocluster 'double' hints at other shape changing particles

New analysis approach brings two unique atomic structures into focus

Chemically the same, graphite and diamonds are as physically distinct as two minerals can be, one opaque and soft, the other translucent and hard. What makes...

All Focus news of the innovation-report >>>

Anzeige

Anzeige

Event News

ERES 2016: The largest conference in the European real estate industry

09.06.2016 | Event News

Networking 4.0: International Laser Technology Congress AKL’16 Shows New Ways of Cooperations

24.05.2016 | Event News

Challenges of rural labor markets

20.05.2016 | Event News

 
Latest News

Nanoscientists develop the 'ultimate discovery tool'

24.06.2016 | Materials Sciences

Russian physicists create a high-precision 'quantum ruler'

24.06.2016 | Physics and Astronomy

Hubble confirms new dark spot on Neptune

24.06.2016 | Physics and Astronomy

VideoLinks
B2B-VideoLinks
More VideoLinks >>>