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CEOverture...
Another year, another step forward for fluorous technology. By most any metric, interest in and utilization of fluorous approaches toward making, purifying and immobilizing a wide range of substances continues to grow rapidly. For example, citations to fluorous chemistry passed the 1,000 mark in Chemical Abstracts this year- an excellent indicator of the volume of basic research that is taking place around the globe. With a month to go, there were already 180 citations in 2006, surpassing the 2005 12 month total of 168. Have a look below to see some of the highlights of 2006, and be sure to visit our website to see what FTI has to offer. As 2006 winds down, the team here at FTI would like to wish everyone a Happy Holiday season. We look forward to doing even greater things together in 2007!
Cheers,
Phil
Philip E. Yeske
President & CEO
Fluorous Small Molecule Applications
The synthesis and purification of small molecules using fluorous techniques continued to expand in 2006 with fluorous tagging strategies, fluorous catalysis, and fluorous library production taking center stage. In tagging, Wilcox and Curran(1) reported a double tagging strategy using oligoethylene glycol (OEG) tags of varying length in combination with fluorous tags of varying length to effect orthogonal separations. Prof. John Valliant at McMaster University, meanwhile, used a reactive fluorous tag for the "carrier-free" synthesis of I-125 containing radiopharmaceuticals(2). High effective specific activities and purities were obtained through a very simple fluorous purification process. In catalysis, both fluorous liquid-liquid and solid phase extractions were extensively reported in 2006 for the facile separation and recycling of fluorous modified catalysts. Some examples include the use of fluorous Lewis acids in biphasic reactions(3-6), fluorous based olefin metathesis chemistry(7,8), and fluorous organocatalysts(9-11). For the production of compound libraries using fluorous techniques, 2006 saw development efforts in both new chemistries and new fluorous separation techniques, including automated FSPE's(21) and parallel F-HPLC(22), both designed to improve the overall throughput of fluorous based separations. The work described above along with many others in 2006 continues to demonstrate the value of fluorous techniques in small molecule preparation and to push fluorous chemistry into new arenas.
For a more extensive listing of 2006 references in fluorous small molecule applications, please visit our website.
Peptides, Carbohydrates, & Oligonucleotides
The increased use of fluorous tags in peptide, oligonucleotide, and carbohydrate synthesis, purification, and analysis continued in 2006. Fluorous tags have proven to provide a unique orthogonal purification method for biomolecules which are often very difficult to purify by other methods. Literature reports describing the fluorous assisted solid phase synthesis of beta-peptides(1) and N-methyl-pyrrole polyamides(2), along with the fluorous phase synthesis of traditional peptides have all been described. In oligonucleotides, the highly regarded Glen Reports(3) recently summarized the use of fluorous DMT phosphoramidites in DNA synthesis. It was noted that fluorous techniques are marked by high recoveries and selectivities of synthetic oligos, particularly sequences >50-mers. In carbohydrates and glycopeptides, researchers from the Noguchi institute continue to pave the way in fluorous phase synthesis utilizing liquid-liquid based separations(9-11). At the 2006 ACS Meeting in San Francisco, Prof. Nicola Pohl presented an update on her group's use of fluorous tags in carbohydrate synthesis, including development of an automated synthesis and FSPE protocol, a very exciting advance in oligosaccharide chemistry(23). For an excellent recent review on fluorous applications in biomolecule chemistry, please see Kumar, K. et al, Curr. Opin. Chem. Biol. 2006, 10, 1. As the above highlights demonstrate, biomolecule purification using fluorous techniques is a rapidly expanding area and one that is primed for even more exciting developments in 2007.
For these and other 2006 references in fluorous biomolecule applications, please visit our website.
Let's Get Small
Another major trend in fluorous chemistry for 2006 was its increased use in micro- and nano- applications. One of the major strengths of fluorous chemistry is its scalability, either large or small scale. Among the published examples in 2006, one of the most interesting was the work of Mikami and co-workers who reported the fluorous Lewis acid catalyzed Baeyer-Villager oxidation of cyclic ketones within a nanoflow controlled microreactor(1). Dramatically higher yields and regioselectivities were observed compared to the corresponding batch reaction. 2006 also saw exciting developments in fluorous nanotechnology. Fujita and co-worker(2) reported the formation of fluorous "nanodroplets" using fluorous Pd complexes and the selective entrapment of fluorous alkanes within those nanodroplets. Other examples of miniaturized fluorous chemistry included the fluorous phase partitioning of nanoparticles(3) and fluorous solid phase extraction within a microfluidic device(4). Look for small scale fluorous applications to become more common as micro- and nano- technologies continue their dramatic growth.
For these and other 2006 references in fluorous micro and nano applications, please visit our website.
Want to Get Started in 2007?
Are you intrigued by the potential of fluorous chemistry and separation and would like to learn more? There's several ways to learn more beyond scouring the available open literature and the many references listed above. 2006 saw the publication of several excellent reviews describing either fluorous chemistry in general or its use in particular applications, such as microwave reactions. You can find these listed on the FTI website. Another very recent educational resource is the Sigma-Aldrich Cheminar™ on fluorous techniques. Sigma-Aldrich carries over 70 FTI products through the Aldrich and Fluka catalogs. The Cheminar™ is an online educational seminar that was produced in conjunction with FTI and provides an excellent overview for those interested in "light" fluorous applications utilizing FSPE. Finally, contact FTI directly! E-mail us or call us (412-826-3050) and we will be happy to answer any questions that you may have.
What's Planned at FTI for 2007?
2007 not only brings a New Year to all of us but many new things to look forward to. At FTI we are looking forward to the introduction of new products and a new look. Coming in 2007 are:
- Launch of Fluorous Microarray Slides
- Introduction of Double-tagged Fluorous reagents
- Fluorous silica packed Pipette Tips for Proteomics
- 24 and 96 Deep Well Plates for CombiChem & Parallel Synthesis
- Next Generation of Fluorous Silica Gel
- An Updated Product Catalog and Website