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Fluorous Carbohydrate Synthesis and Oligosaccharide Microarrays for Glycomics

Benefits of Fluorous Carbohydrate Synthesis

  • Access difficult to make oligosaccharides in a fast, cost effective manner
  • Increase productivity by using a single general purification method for all intermediates and final products.
  • Minimize cost by lowering the equivalents of reagents and monosachharide units
  • Ensure complete reaction through easy reaction monitoring using standard analytical methods
  • Simplify resynthesis and scale-up due to accurate and predictable scalability.
  • Reduce the amount of steps needed to synthesize and immobilize a carbohydrate.

Oligosacchride and carbohydrate synthesis can be a challenge. Fluorous Technologies provides industry-leading tools to tag oligosaccharide sequences and modify microarray content. Fluorous assisted carbohydrate synthesis can be used either in conjunction with solid-phase syntheses or in solution phase syntheses to provied maximum process flexibility. We'll help you meet the challenge of carbohydrate synthesis, and make your research faster, simpler, and more cost effective.

Carbohydrate Synthesis

The use of fluorous tags in conjunction with solid phase oligosacchardie synthesis was initially described by Seeberger and co-workers. The basic methodology uses a carbohydrate linked to a solid phase bead to build the oligosaccharide chain. After each glycosylationn step, any deletion sequences are capped with a fluorous tag.

Separation of diverse chemical structures using a single method

Once the synthesis is complete the undesired fluorous tagged deletions are easily separated from the complete oligosaccharide sequence by fluorous solid phase extraction (FSPE). Conversely, a fluorous terminal tagging strategy can also be employed where all the truncated sequences are capped with a non-fluorous capping agent and the desired full sequence is fluorous tagged as the final step. FSPE can then be used to separate all the undesired sequences from the fluorous tagged oligosacchride.

Solution Phase Advantages

In solution phase syntheses, a fluorous tag is used in place of the solid support. This provides several advantages over solid phase approaches such as reaction monitoring, solution phase kinetics, and less equivalents of reagents and saccharide monomers being used. Each of the reaction products can be separated from the reagents and excess monomer by FSPE or FLLE. In addition, fluorous supported oligosaccharide synthesis can be automated. Since fluorous supported chemistry is solution phase chemistry it also means that scale-up is easy and predictable making re-synthesis a snap.

Easily form Oligosaccharide Microarrays for Glycomics

Carbohydrates synthesized with fluorous tags can be directly immobilized onto fluorous-modified glass slides. If you already have carbohydrate content, it can be readily fluorous tagged, so you can take advantage of the unique features of fluorous microarrays. Read more about this easy way to create microarrays on our microarraying page.

Oligosaccharide synthesis and microarraying for glycomics.

Get Started Today

Fluorous Technologies Inc. can provide you with all the reagents, separation media, and guidance you need to produce oligosacchrides for your research. View our product line by visiting the links under the Related Products section to the left. Join the discussion around fluorous carbohydrate synthesis at F-Blog.

Selected References

  • Palmacci, E. R.; Hewitt, M. C.; Seeberger, P. H. Angewandte Chemie, International Edition 2001, 40, 4433-4437.
  • Carrel, F. R.; Seeberger, P. H. J. Org. Chem. Journal of Organic Chemistry 2008, 73, 2058-2065.
  • Ko, K.-S.; Jaipuri, F. A.; Pohl, N. L. Journal of the American Chemical Society 2005, 127, 13162-13163.
  • Mizuno, M.; Kitazawa, S.; Goto, K. J. Fluorine Chem. 2008, 129, 955-960.
  • Pohl, N. L. ACS Symp. Ser. ACS Symposium Series 2008, 990, 272-287.
  • Chen, G. S.; Pohl, N. L., Org. Lett. 2008, 785