Labeling under flow conditions: Understanding added applications

Stepping outside traditional synthetic labs into specialty applications is not always something we are looking for in the literature, but it is an excellent way to see different techniques which might be utilized in your own labs. Neil Vasdev’s group at the Harvard Medical School specializes in labeling compounds for more advanced analysis – imaging techniques as tracers for the study of advanced disease states. His group has been using flow chemistry and flow hydrogenation for some time so I thought it be interesting for everyone to see the work.

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Two recent publications illustrate their research. In the first publication Chem Commun 2013, 49, 8755  the group uses three examples where they incorporate a label for study into an advanced intermediate C11 or F18 through a microfluidic reaction, followed by a strategic deprotection of a benzyl  group or CBz under flow hydrogenation. Without going into significant detail, the group absolutely needed an optimized profile for these sorts of reactions due to the nature of the labeling and ran a number of studies with variations of solvent, temperature and pressure. It is worth the read to understand the significance of finding a fast, reliable method for multiple processes for their strategies. Labeling and incorporation of more substituents are being explored using these technologies then the literature provides — and the number of uses for flow hydrogenation can’t be undervalued with all of the transformations within.

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The second paper, which I found to be even more interesting because it shows the application of the strategy — the imaging of the compounds made. I would be remiss if I didn’t mention Steven Liang from MGH as a critical part of both papers…..but the paper describes a specific compound made under microfluidic flow conditions for the labeling and subsequent study. Mol Imaging. 2014 Sep 1;13:1-5 is where you can find the citation but if you are exceptional at google (hehe) then you can find a pdf of the article.

Enjoy the articles but keep an eye toward uses of these flow techniques in your own discovery efforts — several new applications show up every week. Happy Reading!

 

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