Fluorous Techniques Complement and Enhance other Technologies
April 2010 Fluorous Technical Newsletter
CEOverture
Often we use this forum to communicate the benefit of integrating fluorous techniques into your research workflow because of the synthesis, separation and immobilization problems it can solve. Compatibility is another significant part of the value of fluorous technology. The ability to carry out your research as you always have, using equipment already in place, is a major benefit. Below are a few examples that demonstrate the breadth of fluorous compatibility and the ease with which fluorous techniques can be implemented. If you haven’t already, why not give it a try? Please contact us and we will provide you with all the materials, guidance, and expertise needed to make full use of the power of fluorous techniques.
Cheers,
Philip E. Yeske
President & CEO
Fluorous Technologies Inc.
Fluorous and Microwave
Microwave-assisted synthesis has now been used extensively in various applications including small molecule synthesis, solid phase peptide synthesis, and proteomics. Modern single-mode microwave instruments can provide focused heating in a highly controlled fashion to many chemical and enzymatic reactions often times resulting in faster, cleaner reactions with greater yields. It still does not, however, address the issue of purification. That’s where fluorous techniques can help.
Using fluorous tags and reagents with microwave-assisted chemistry enhances both synthesis and purification. A good example of this complementarity was recently published in J. Combi. Chem. by Liu et al. The benzodiazopinedione library synthesis used a fluorous sulfonate tag and FSPE purification after each step. A microwave assisted Suzuki reaction which provided the final compound with concomitant detagging.
For more examples of using fluorous with microwave technology, view our F-Blog microwave archive. For complete details about Fluorous Solid Phase Extraction (FSPE) including available product listings, related applications, and application notes please visit our FSPE Technology page.
Fluorous and Solid-Phase synthesis
Solid-phase synthesis techniques have been utilized for decades; first in peptide and oligonucleotide synthesis, then in small molecule synthesis, and finally in oligosaccharide synthesis. The strength of solid-phase synthesis lies in ease of isolation. The weaknesses of solid phase synthesis lie in purification. The heterogeneous nature of solid phase synthesis can result in inconsistent results due to incomplete reaction, slow reactions kinetics, and difficult reaction monitoring. This often makes final purification after removal of the solid-phase support a laborious and time-consuming process, especially for the synthesis of oligomeric biomolecules.
Fluorous techniques can help overcome these issues. Several strategies, including fluorous tagging and fluorous capping, use fluorous solid phase extraction (FSPE) to easily separate the desired product from undesired deletion sequences. Peptides and oligonucleotides have been produced using these fluorous-enhanced solid phase synthesis strategies. A recent example from the literature of a fluorous tagging strategy was employed by Seeberger et al in the solid phase synthesis of oligosaccharides. In this work, the researchers capped any deletion sequences with an acetyl group then used a fluorous silane to tag the final desired length oligosaccharide. The fluorous tagged oligosaccharide was then easily separated from the deletion sequences by FSPE.
Learn more about using fluorous with solid-phase synthesis in our Biomolecule Synthesis section. Our peptide, oligonucleotide and carbohydrate synthesis pages each have links to product listings, application notes, and references.
Fluorous and Microfluidics
Miniaturization of reactions through the use of microfluidic devices is an increased area of interest. Compared to traditional flask-based chemistry, microreactor based chemistry has several advantages including ease of scalability, increased process safety and control, and increased energy efficiency. Once again, these are advantages incurred during synthesis, but they do not address purification and that is where fluorous techniques add value.
In a prime example, Prof. Mizuno and co-workers at The Noguchi Institute used a microreactor in conjunction with fluorous liquid-liquid extraction (FLLE) to synthesize a protected monosaccharide unit quickly and efficiently. Each of the six reactions in the synthetic sequence was conducted in a microreactor and the fluorous tagged product isolated by FLLE. The optimized sequence eventually resulted in a process that completed the entire 6 step sequence in only 9 hours. This could only be accomplished due to the combined efficiency of the microreactor and the fluorous purifications.
Stay abreast of the latest developments in fluorous liquid liquid extraction and microfluidics through F-Blog. Background information on FLLE and the powerful technique of solvent tuning can be found on our FLLE Technology page.
The Fine Print
Fluorous Technologies is a chemical technology company devoted to the development and commercialization of fluorous products for the life science market. The company uses its patented technology to solve synthesis and separation problems spanning the entire drug discovery and development process. Fluorous chemistry enhances a wide range of applications, including medicinal chemistry, combinatorial chemistry, catalysis, biomolecule production, and proteomics. For more information, please visit: http://fluorous.com
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