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A new method for clicking molecules together
Date:7/22/2013

Thiols are sulfur-containing molecules found in most proteins of the human body. Characterized by their 'garlicky' smell, they also give coffee, sweat and the spray of skunks their unique odor. Because they are so widespread in biology, medicine and materials science, thiols are ideal targets for connecting molecules like drugs or polymers together, except that they must first be fitted with a chemical group that acts like an adaptor to other molecules. One of the most potentially useful of these 'adaptors' are the alkynes, which can be extremely powerful in bioconjugation. The problem is that adding alkynes to thiols ('alkynylation') has been too difficult to be of any use outside the lab. But now, in a patent-pending publication in the Journal of the American Chemical Society, EPFL scientists have found a way to make the connection in five minutes and at room temperature, paving the way to commercial, medical and perhaps industrial applications.

Thiol alkynylation is part of 'modular' or 'click' chemistry, a field that has far-reaching applications in drug discovery, nanotechnology and bioengineering. The idea is to synthesize large molecules by quickly "clicking together" smaller ones, allowing us to change previously-inaccessible complex molecules. Although relatively new, click chemistry is actually inspired by natural processes. For example, after being synthesized in the cell, proteins are further modified with carbohydrates and lipids to change their properties. This process, known as post-translational modification, involves a whole host of complex enzymes that can be sidestepped in the lab by using click chemistry methods.

In order to achieve alkynylation, researchers from the group of Jerme Waser at EPFL used an alkyne-transfer reagent called TIPS-ethynyl-benziodoxolone (TIPS-EBX), which they have made commercially available by collaborating with Sigma-Aldrich. The EPFL researchers had found that previous alkynylation reactio
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Contact: Nik Papageorgiou
n.papageorgiou@epfl.ch
41-216-933-2105
Ecole Polytechnique Fdrale de Lausanne
Source:Eurekalert

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