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CEOverture...
Usually this space is reserved for a commentary on what is in this newsletter, but today I want to talk about what’s not in this newsletter. An important part of FTI’s growth and development continues to be participation in the SBIR/STTR grant program, administered by the United States Small Business Administration. Recently FTI was awarded a Phase II grant by the NIH to further explore the commercial utility of fluorous techniques for making, purifying and arraying biomolecules such as peptides and carbohydrates. We’re starting to generate some exciting results together with our chief collaborator, Prof. Nicola Pohl at Iowa State University. Both FTI and Prof. Pohl have submitted several abstracts for the next ACS National Meeting in New Orleans, so stay tuned for more details on our progress. In the meantime, don’t forget your daily ration of Vitamin F!
Cheers,
Phil
Philip E. Yeske
President & CEO
Fluorous Mitsunobu Reaction at Work
One of the most popular applications of fluorous techniques is the fluorous Mitsunobu reaction utilizing a fluorous phosphine in combination with fluorous DIAD. Since its introduction there have been many examples reported in the literature. Anyone who has conducted a Mitsunobu reaction realizes the benefits, and disadvantages, of this reaction. While it performs remarkably well in forming carbon-heteroatom bonds that might otherwise be difficult to form, the removal of the hydrazide and phosphine by-products can often times be problematic. The fluorous Mitsunobu reagents provide similar reactivity to traditional DIAD and TPP, but provide the benefit of easy clean-up using F-SPE or F-LLE.
Two recent examples in the literature include a report by Prof. Nicolas Winssinger at the Universite Louis Pasteur in Strasbourg describing the synthesis of resorcylic acid lactones (Angew. Chemie Intl. Ed., 2007, 46, 6899). The macrolactonization shown below to form the requisite 14-member lactone was carried out using F-DIAD and F-TPP. The second example was reported by Prof. John Porco and co-workers from Boston University (Angew. Chemie Intl. Ed., 2007, 46, 67831), who used a Mitsunobu to effect the key linkage between a phenol and a glycone in their synthesis of (-)-silvestrol. Interestingly, in this latter case, F-TPP was used in conjunction with traditional DIAD, since it was the triphenylphosphine oxide which was difficult to remove from the product. In each of these cases F-SPE was used to remove the fluorous by-products.
So if you love the Mitsunobu reaction for its chemistry, but hate the purifications afterwards, try the fluorous approach and see the benefits. If you require technical assistance please do not hesitate to contact us and we will be glad to provide you with the materials and expertise to help you succeed.
Fluorous Small Molecule Microarray News
Last month’s FTI Newsletter highlighted two recent publications, one from Prof. David Spring at Cambridge University and the other from Prof. Stuart Schreiber at Harvard University, which validated the use of fluorous immobilization techniques in small molecule microarrays. The Schreiber publication was designated a VIP (Very Important Paper) by the editors of Angewandte Chemie. We weren’t the only ones that noticed as these papers were also highlighted in the Science Concentrates section of the Oct. 1, 2007 Chemical & Engineering News. Fluorous based microarrays provide excellent spot morphology and signal-to-noise along with low and uniform background fluorescence. FTI provided fluorous tags as well as fluorous modified glass slides to both of these groups and can provide you with the same types of products to produce better performing microarrays. If you would like more information, please contact us.
J. Combi. Chem. Annual Reviews
Each year the Journal of Combinatorial Chemistry publishes a review which provides an overview on the progress of parallel and high-throughput synthesis. This annual report is generally considered one of the most informative review articles in combinatorial chemistry. The most recent part of the series, “Comprehensive Survey of Chemical Libraries for Drug Discovery and Chemical Biology: 2006”, has just been released online (J. Combi.Chem. 2007, ASAP). With over 60 fluorous papers cited within the review, the influence and value of fluorous techniques in library synthesis is clearly evident. In addition to listing newly developed fluorous reagents, scavengers, and catalysts in the tables, several examples of fluorous chemistry for library synthesis are also highlighted, including fluorous mixture synthesis, microwave-assisted diversity-oriented synthesis, and fluorous tagging in diversity-oriented synthesis. For more details on each of these elements, please see the F-blog post which describes this review in more detail.
FTI Academic Program
Many of you may not be aware of our “FTI Academic Program”. This program is offered to our academic colleagues and is designed to provide them with an opportunity to use FluoroFlash® reagents and sorbents at a discounted price – 25% discount on fluorous reagents and 15% discount on fluorous sorbents. In exchange, we ask for an overview of the research you are planning and a summary of your results or copy of your published paper once completed. The goal of this program is simple - we see the opportunity to apply fluorous chemistry in a broad range of applications by working with acknowledged thought leaders who are exploring new areas and expanding upon existing ones. The “FTI Academic Program” has been quite successful with many of our participants publishing papers highlighted here in our newsletter. Sound like something you may be interested in? Just contact us for additional details on how to join the growing number of academic participants!
What's Up at FTI...
In keeping up with the reality show craze, we are undergoing our own ‘makeover’ of sorts. Our first step was to update the content on our website. Many of our most popular pages, for example the peptides page, application notes, and presentation downloads have been updated to include the most recent advances in fluorous chemistry. We have also included the most relevant and up to date references from the peer-reviewed literature for each of these pages. All of this is leading up to a new FTI website slated for 1Q08 release with easier navigation and a more user-friendly format. In preparation for our ‘new look’, if there is anything that you would like to see or content that you would like us to include, please contact us with your comments.
F-Blog…All Things Fluorous is our way of getting the latest fluorous literature and events to you in a very timely manner. Since its inception, our postings have continued at 2-3 per week and our readership continues to grow at a steady pace. If you are reading the F-Blog, take a minute to register. This not only allows you to comment on any of the postings but also gives you a 20% discount on the next order you place with us.
Anytime you are on the web and need further information, just click on the "Contact Us" button located on the top corner of each page. Here you will find phone, fax and email contact information.