Forum for Science, Industry and Business

Sponsored by:     3M 
Search our Site:

 

Prevent This!

24.05.2012
Efficient Preparation of a Set of Potential Glycosidase Inhibitors

In many biological and pathological processes, glycosidase enzymes attack glycosidic bonds in carbohydrates, glycoproteins, and glycolipids. The ability to modify or block these processes by specific glycosidase inhibitors forms the basis for their potential use in the treatment of viral infections, cancer, and genetic disorders.

A Dutch team led by Herman S. Overkleeft has now developed a method that allows the synthesis of 8 of the 16 possible configurational isomers of the inhibitor candidate deoxynojirimycin, which will allow comprehensive medicinal chemistry screening of this library. As the scientists report in the European Journal of Organic Chemistry, their technique requires the use of a common precursor to prepare all eight compounds of biological interest.

Deoxynojirimycin and its derivatives have been long pursued by organic and medicinal chemists as a result of their potential as glycosidase inhibitors. Many groups now pursue these compounds for their application in the treatment of genetic disorders and type II diabetes. Consequently, many synthetic studies on deoxynojirimycins have appeared and continue to appear; however, synthetic strategies that allow different configurational isomers to be prepared in a concise fashion are scarce.

This synthesis of such a library is important so that the compounds can be studied side by side. This technique can give chemists important insight into which structural features lead to higher levels of biological activity.

The scientists' procedure involves the use of a common cyanohydrin as the starting material, which is easily accessible in large quantities. The cyanohydrin is then transformed into cyclic building blocks from which the individual isomers can be assembled by using typical organic transformations. This work complements the large body of literature on the synthesis of 1-deoxynojirimycin derivatives with the distinguishing feature that eight stereoisomers of this important class of glycosidase inhibitors can be derived from a common precursor in an efficient manner. This team is therefore well on its way to helping scientists screen a diverse range of potential drugs that may lead to the treatment of important diseases.

Author: Herman S. Overkleeft, Universiteit Leiden (The Netherlands), http://biosyn.lic.leidenuniv.nl/people/overkleeft
Title: Synthesis of Eight 1-Deoxynojirimycin Isomers from a Single Chiral Cyanohydrin

European Journal of Organic Chemistry, Permalink to the article: http://dx.doi.org/10.1002/ejoc.2012003

Herman S. Overkleeft | Wiley-VCH
Further information:
http://www.wiley.com

More articles from Life Sciences:

nachricht Tag it EASI – a new method for accurate protein analysis
20.06.2018 | Max-Planck-Institut für Biochemie

nachricht How to track and trace a protein: Nanosensors monitor intracellular deliveries
19.06.2018 | Universität Basel

All articles from Life Sciences >>>

The most recent press releases about innovation >>>

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

Im Focus: Temperature-controlled fiber-optic light source with liquid core

In a recent publication in the renowned journal Optica, scientists of Leibniz-Institute of Photonic Technology (Leibniz IPHT) in Jena showed that they can accurately control the optical properties of liquid-core fiber lasers and therefore their spectral band width by temperature and pressure tuning.

Already last year, the researchers provided experimental proof of a new dynamic of hybrid solitons– temporally and spectrally stationary light waves resulting...

Im Focus: Overdosing on Calcium

Nano crystals impact stem cell fate during bone formation

Scientists from the University of Freiburg and the University of Basel identified a master regulator for bone regeneration. Prasad Shastri, Professor of...

Im Focus: AchemAsia 2019 will take place in Shanghai

Moving into its fourth decade, AchemAsia is setting out for new horizons: The International Expo and Innovation Forum for Sustainable Chemical Production will take place from 21-23 May 2019 in Shanghai, China. With an updated event profile, the eleventh edition focusses on topics that are especially relevant for the Chinese process industry, putting a strong emphasis on sustainability and innovation.

Founded in 1989 as a spin-off of ACHEMA to cater to the needs of China’s then developing industry, AchemAsia has since grown into a platform where the latest...

Im Focus: First real-time test of Li-Fi utilization for the industrial Internet of Things

The BMBF-funded OWICELLS project was successfully completed with a final presentation at the BMW plant in Munich. The presentation demonstrated a Li-Fi communication with a mobile robot, while the robot carried out usual production processes (welding, moving and testing parts) in a 5x5m² production cell. The robust, optical wireless transmission is based on spatial diversity; in other words, data is sent and received simultaneously by several LEDs and several photodiodes. The system can transmit data at more than 100 Mbit/s and five milliseconds latency.

Modern production technologies in the automobile industry must become more flexible in order to fulfil individual customer requirements.

Im Focus: Sharp images with flexible fibers

An international team of scientists has discovered a new way to transfer image information through multimodal fibers with almost no distortion - even if the fiber is bent. The results of the study, to which scientist from the Leibniz-Institute of Photonic Technology Jena (Leibniz IPHT) contributed, were published on 6thJune in the highly-cited journal Physical Review Letters.

Endoscopes allow doctors to see into a patient’s body like through a keyhole. Typically, the images are transmitted via a bundle of several hundreds of optical...

All Focus news of the innovation-report >>>

Anzeige

Anzeige

VideoLinks
Industry & Economy
Event News

Munich conference on asteroid detection, tracking and defense

13.06.2018 | Event News

2nd International Baltic Earth Conference in Denmark: “The Baltic Sea region in Transition”

08.06.2018 | Event News

ISEKI_Food 2018: Conference with Holistic View of Food Production

05.06.2018 | Event News

 
Latest News

Creating a new composite fuel for new-generation fast reactors

20.06.2018 | Materials Sciences

Game-changing finding pushes 3D-printing to the molecular limit

20.06.2018 | Materials Sciences

Could this material enable autonomous vehicles to come to market sooner?

20.06.2018 | Materials Sciences

VideoLinks
Science & Research
Overview of more VideoLinks >>>