Today was the big day for ISoFT’09 with lectures starting at 8 AM and lasting until 5 PM. In total there was 18 talks with topics ranging from small molecule chemistry, materials, oligonucleotides, carbohydrates, sensors, and carbohydrates. With that many talks it is going to be impossible to mention all of them and for that I apologize. Even so there were several things that really caught my attention.
The morning started with Prof. Phillipe Buhlmann giving an overview on his group’s work in using fluorous membranes in developing sensors for the detection of specific ions. They were able to achieve remarkable selectivity for specific ions using fluorous membranes and ions. One of the lessons from this talk was the collaborative nature of the research with the syntheses for many of his fluorous ionophores being conducted by John Gladysz and Josef Rabai.
Another talk which stood out for me was Prof. Jean-Marc Vincent’s work with fluorous copper carboxylates. They have worked with these before and biphasic systems, but what was really interesting was that the solvation characteristics of copper carboxylates changed dramatically by the presence or absence of an ethylene spacer between the perfluorocarbon moiety and the carboxylate. They were also able to immobilize these complexes on Teflon tape then use the modified Teflon tape to complex porphyrins. Really fascinating work which demonstrates the importance of spacers.
Prof. Takeshi Wada used light fluorous techniques for oligonucleotide synthesis which was also very interesting. Their objective was to prepare oligonucldotides modified at the phosphonate in order to provide oligonucleotides which are more stable to nucleases. Oligonucleotide stability is a real problem when it comes to therapeutic oligos and this one approach to mitigating the problem. Similarly, Prof. Neil Marsh presented his work in using fluorous amino acids in the synthesis of peptides and proteins which are stable to hydrolysis from proteases.
The last talk that I want to mention in this post was from Prof. Mamoru Minuzo who is primarily involved in fluorous carbohydrate synthesis. The one aspect of his talk that I was most impressed with was the microreactor based monosaccharide synthesis. As he pointed out in his talk, often times the rate limiting step in an oligosaccharide synthesis is not the coupling of the individual saccharide units, but rather synthesis of the monomers. They have tried to make this part of the process more efficient by using a microreactor. Their big contribution was being able to integrate the synthetic reactions with the separation using a fluorous tag and fluorous liquid-liquid extraction. The example provided was a six step synthesis of a monosaccharide which was completed in 9 hours to provide 240 mg of monomer. That is a very impressive performance. Anyone would be hard-pressed to complete a six step synthesis in 9 hours!
Over the next few weeks, we’ll try and collect as many of the talks as possible and put them up on the FTI website. So even if you weren’t here, we can hopefully try and share some of the exciting chemistry with you.
The day ended at the Diamond Cross Ranch where we had a horse whispering demonstration and a western BBQ dinner. Both were fantastic and far exceeded my expectations. The night was clear and crisp and the setting simply spectacular as we gathered around campfires making s’mores with a crescent moon and the Teton mountains in the background.
Tomorrow is the fluorous poster session in the morning with the rest of the day free for excursions.