New chemical synthesis method can produce an exciting range of novel compounds

July 04, 2017

Chemists at Nagoya Institute of Technology have developed an innovative chemical reaction system, which could have applications for developing starter molecules for additional synthetic procedures in organic chemistry, as well as pharmaceutical candidates with a potentially wide range of biological activities.

Nagoya, Japan - Given their three-dimensional nature, many chemical compounds can exist in two different forms that are mirror images of each other, called enantiomers. These can have markedly different effects on the human body, so it is often necessary to isolate only one of the forms prior to administration. To avoid this problem, it is possible to develop chemical synthesis methods that produce mostly or exclusively one of the possible enantiomers. This is a salient issue for a class of molecule called aziridines, which include important antibiotics and chemotherapeutic agents, but there still remains substantial scope for manipulating and modifying the reactions by which they are synthesized for a range of applications.

In a new study reported in the journal Angewandte Chemie International Edition, a team of researchers at Nagoya Institute of Technology (NIT) have established a new reaction whereby a group of molecules called 2H-azirines react with phosphite with the help of a catalyst. By applying a variety of catalysts and conditions to this reaction, they managed to produce aziridines at high yield and with a single enantiomer comprising as much as 98% of the total product.

Little previous work has focused on trying to produce a high level of a single enantiomer from reactions with 2H-azirines because these compounds are not very reactive. Here, the researchers chose to employ a phosphite, comprising phosphor and oxygen atoms, for the reaction with the 2H-azirines because of its ability to contribute or donate electrons in this reaction, promoting the transformation of azirines to aziridines.

"In the reaction of 2H-azirines with phosphite, we applied various chiral catalysts to see their effects," says Daiki Hayama of the Graduate School of Engineering, NIT. "Once we identified a catalyst that gave both a good overall yield and a high proportion of a single enantiomer in the reaction, we then focused on also optimizing the reaction conditions."

Once a particularly effective combination of conditions was identified, the team also tested structural variations of the azirine used as starting material in the reaction along with the best catalyst found in the previous experiment, again achieving high yields and high rates of production of one of the possible enantiomers.

"Our results show that this reaction is very enantioselective and works well for a wide range of azirines," Prof. Shuichi Nakamura says. "This approach should be very useful for developing new chiral molecules potentially with interesting features, both for medical applications and for further work in the field of organic chemistry."

Nagoya Institute of Technology

Related Technology Articles from Brightsurf:

October issue SLAS Technology now available
The October issue of SLAS Technology features the cover article, 'Role of Digital Microfl-uidics in Enabling Access to Laboratory Automation and Making Biology Programmable' by Varun B.

Robot technology for everyone or only for the average person?
Robot technology is being used more and more in health rehabilitation and in working life.

Novel biomarker technology for cancer diagnostics
A new way of identifying cancer biomarkers has been developed by researchers at Lund University in Sweden.

Technology innovation for neurology
TU Graz researcher Francesco Greco has developed ultra-light tattoo electrodes that are hardly noticeable on the skin and make long-term measurements of brain activity cheaper and easier.

April's SLAS Technology is now available
April's Edition of SLAS Technology Features Cover Article, 'CURATE.AI: Optimizing Personalized Medicine with Artificial Intelligence'.

Technology in higher education: learning with it instead of from it
Technology has shifted the way that professors teach students in higher education.

Post-lithium technology
Next-generation batteries will probably see the replacement of lithium ions by more abundant and environmentally benign alkali metal or multivalent ions.

Rethinking the role of technology in the classroom
Introducing tablets and laptops to the classroom has certain educational virtues, according to Annahita Ball, an assistant professor in the University at Buffalo School of Social Work, but her research suggests that tech has its limitations as well.

The science and technology of FAST
The Five hundred-meter Aperture Spherical radio Telescope (FAST), located in a radio quiet zone, with the targets (e.g., radio pulsars and neutron stars, galactic and extragalactic 21-cm HI emission).

AI technology could help protect water supplies
Progress on new artificial intelligence (AI) technology could make monitoring at water treatment plants cheaper and easier and help safeguard public health.

Read More: Technology News and Technology Current Events is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to