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FluoroFlash® Protective Tags

FluoroFlash® protecting group tags, such as F17-Boc-ON (Fig. 1), are fluorous versions of commonly employed protective group reagents used in chemical synthesis.  These tags serve a dual purpose by protecting the functional group and providing a handle for easy purification.  A substrate molecule tagged with a fluorous protective group is easily separated from other non-fluorous reaction components via the use of fluorous sorbents in a fluorous solid phase extraction (F-SPE).  Fluorous protecting group tags have been used extensively in total synthesis, multi-component reactions, and microwave reactions. [1]  The reactivity of FluoroFlash® tags closely mirrors that of traditional protecting groups simplifying incorporation of a fluorous tag into existing procedures.  Some FluoroFlash® protecting group tags are also available in homologous series with different fluorous chain lengths for use in Fluorous Mixture Synthesis. (FMS). [2]  Currently, FTI offers tags to protect a variety of functional groups including alcohols, carboxylic acids and amines.

FluoroFlash® Reagents

Fluorous reagents are fluorous versions of compounds commonly employed in specific synthetic reactions. FluoroFlash® reagents  exhibit similar reactivity to their non-fluorous analogs, but provide the added benefit of easy removal after reaction using fluorous solid phase extraction (F-SPE). [3]  Examples of these products include the fluorous DIAD reagent and fluorous phosphine reagent shown in Figure 2, which can be used to conduct Mitsunobu reactions with facile removal of all reaction by-products by F-SPE.  Examples of reagents offered by FTI include fluorous versions of CDMT and Mukaiyama’s salt for amide couplings, tributyltin reagents, and diacetoxy iodobenzene for oxidations.  Various other reagents for are also available all of which can be removed using fluorous separation techniques.

FluoroFlash® Scavengers

Fluorous scavengers such as the thiol and isocyanate pictured in Figure 3 can capture excess reagents and be easily removed via solid phase extraction over FluoroFlash® silica gel analogous to solid phase scavenging reaction.  Fluorous scavengers provide the advantage of being solution phase scavengers which undergo reaction under solution phase kinetics.  Unlike solid phase scavengers, fluorous scavengers are molecules rather than materials and allow for precise stoichiometric control.  The overall benefit is quicker, more complete reactions using fewer equivalents then other scavengers. [4]  There are fluorous scavengers for both electrophilic and nucleophilic reagents.

FluoroFlash® Bioreagents

FTI offers a line of reagents specifically designed for the enrichment of specific molecular classes from biologically derived samples.  These bioreagents are designed to chemically tag compounds such as Cys residues, terminal amines, carbonyl compounds, or other functionality with a fluorous tag.  A fluorous solid phase extraction can then be used to separate the non-tagged components from the sample from the tagged components.  Fluorous bioreagents provide an alternative to biotin-avidin based enrichment strategies and possess very low non-specific binding with easy recovery of either the tagged or the non-tagged portion.  In addition, they have excellent MS and MSn behavior and are completely compatible with protein and peptide identification software.  These reagents have been used in both proteomics [5] and metabolomics [6] applications.

Fluorous Building Blocks

The wide applicability of fluorous techniques to a variety of fields prevents FTI from providing everyone the exact compound needed.  For those materials that we do not include in our catalog, we provide a wide range of base fluorous materials for researchers to incorporate in the preparation of the fluorous tagged compound desired. 

FluoroFlash® Sorbents

FluoroFlash® sorbents are chromatographic materials that have been specially modified and designed to separate fluorous compounds from non-fluorous compounds.  Fluorous based separations are marked by their simplicity, generality, and exceptional selectivity.  Fluorous separations have been used for the synthesis and purification of a wide variety of molecular classes including small molecules, peptides, oligonucleotides, and carbohydrates. [7]  FluoroFlash® sorbents are available either in bulk or pre-packed in a number of formats for F-SPE and HPLC applications.

FluoroFlash® sorbents are available in the following product formats:

• TLC plates for reaction monitoring and FSPE development
• Solid phase extraction cartridges for single reaction purification
• 24, 48, and 96-well plates for high throughput and parallel synthesis applications
• HPLC columns in analytical, semi-preparative, and preparative sizes for reaction monitoring and fluorous mixture synthesis (FMS)
• Flash chromatography columns for automated chromatography systems
• Bulk fluorous sorbents

This product selection provides maximum flexibility in the use of fluorous chemistry including parallel synthesis and purification, parallel synthesis, fluorous mixture synthesis, and synthetic options unavailable through other approaches.

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FluoroFlash® Slides for Immobilization

Fluorous tagged molecules can be non-covalently immobilized onto fluorous modified glass slides to form microarrays.  Fluorous based carbohydrate and small molecule microarrays have been formed and found to provide arrays with excellent spot morphology, low and uniform background fluorescence, and low non-specific binding. [8]   Moreover, the inertness and high selectivity of the surface simplifies workflows by minimizing washing and rinsing steps normally conducted using other surfaces.  FTI provides these slides in both plain and bar-coded versions which are manufactured, packaged, and shipped under some of the highest standards within the industry.

Selected References

1. a)  Zhang, W., Fluorous protecting groups and tags. Handbook of Fluorous Chemistry 2004, 222-236.   b) Zhang, W., Fluorous-enhanced multicomponent reactions for making drug-like library scaffolds. Comb. Chem. High Throughput Screening 2007, 10, (3), 219-229.  c) Zhang, W., Microwave-enhanced high-speed fluorous synthesis. Topics in Current Chemistry 2006, 266, (Microwave Methods in Organic Synthesis), 145-166.
2.  Luo, Z. Y.; Zhang, Q. S.; Oderaotoshi, Y.; Curran, D. P., Fluorous mixture synthesis: A fluorous-tagging strategy for the synthesis and separation of mixtures of organic compounds. Science 2001, 291, (5509), 1766-1769.
3. Curran, D. P., Organic synthesis with light-fluorous reagents, reactants, catalysts, and scavengers. Aldrichimica Acta 2006, 39, (1), 3-9.
4. Chen, C. H.-T.; Zhang, W., Fluorous reagents and scavengers versus solid-supported reagents and scavengers, a reaction rate and kinetic comparison. Molecular Diversity 2005, 9, (4), 353-359.
5. Brittain, S. M.; Ficarro, S. B.; Brock, A.; Peters, E. C., Enrichment and analysis of peptide subsets using fluorous affinity tags and mass spectrometry. Nature Biotechnology 2005, 23, (4), 463-468.
6. Go, E. P.; Uritboonthai, W.; Apon, J. V.; Trauger, S. A.; Nordstrom, A.; O'Maille, G.; Brittain, S. M.; Peters, E. C.; Siuzdak, G., Selective Metabolite and Peptide Capture/Mass Detection Using Fluorous Affinity Tags. J. Proteome Res. 2007, 6, (4), 1492-1499.
7. a) Dandapani, S., Recent applications of fluorous separation methods in organic and bioorganic chemistry. QSAR & Combinatorial Science 2006, 25, (8-9), 681-688.   b) Zhang, W.; Curran, D. P., Synthetic applications of fluorous solid-phase extraction (F-SPE). Tetrahedron 2006, 62, (51), 11837-11865.
8. a) Ko, K.-S.; Jaipuri, F. A.; Pohl, N. L., Fluorous-Based Carbohydrate Microarrays. Journal of the American Chemical Society 2005, 127, (38), 13162-13163.  b) Nicholson, R. L.; Ladlow, M.L.; Spring, D.S. Fluorous tagged small molecule microarrays, Chem. Commun., 2007, DOI: 10.1039/b712906h c) Vegas, A. J.; Bradner, J. E.; Tang, W.; McPherson O. M.; Greenberg, E. F.;  Koehler, A. N.; Schreiber, S. L. Angew. Chem. Intl. Ed. 2007, DOI: 10.1002/anie.200703198.