Fluorous Chemistry Recognized at the 2010 Fall ACS Meeting
July 2010 Fluorous Technical Newsletter
CEOverture
The fall installment of the semi-annual national meeting of the American Chemical Society takes place in Boston next month, and this issue of our technical newsletter is devoted to previewing the conference from a fluorous perspective. As we perused the abstracts, we were struck by the number of ACS award winners, both past and present, that are active in the fluorous research community. For instance, at this meeting Prof. Nicola Pohl and Prof. Robert Linhardt will each receive research achievement awards from the Carbohydrate Division of the ACS, and both plan to describe how fluorous technology enables their work. Looking back, the historical records for these and other prestigious awards from the ACS contain numerous examples of researchers who deployed fluorous techniques as a part of their research. We are, of course, proud of that fact, but credit mostly goes to those who do the work! Congrats to those that have achieved recognition, and to those who haven’t- maybe fluorous can get you there?
Cheers,
Philip E. Yeske
President & CEO
Fluorous Technologies Inc.
Fluorous Small Molecule Chemistry
Fluorous Tags in Novel Heterocyclic Library Synthesis
Five presentations and posters being presented at the ACS Meeting use fluorous techniques in small molecule chemistry. Three from Prof. Wei Zhang and co-workers describe their use of fluorous tagging strategies in the construction of heterocyclic libraries. The Zhang group is also developing fluorous organocatalysts for asymmetric transformations and will present a fourth poster reporting their efforts in that area. Each presentation will contain some previously unpublished work.
Fluorous Mixture Synthesis in Natural Product Research
The fifth fluorous small molecule presentation describes the Curran group’s use of fluorous mixture synthesis (FMS) in the synthesis of phytophthora mating hormone a1. This natural product contains four non-contiguous stereocenters making stereochemical assignment a challenge. By utilizing FMS the researchers are able to quickly prepare all possible stereoisomers to unambiguously assign the stereochemistry of the natural product. This is a strategy that the Curran group has used extensively for natural product structure confirmation and total synthesis. Fluorous mixture synthesis not only reduces the total number of synthetic steps necessary to make all possible stereoisomers, but also strategically encodes isomeric configuration information. With fluorous tags, the solutions to the problems of separation and identification are designed into the synthesis.
For background information and examples, explore our small molecule synthesis web pages. Then visit with the scientists themselves at the ACS Meeting to learn more.
Carbohydrate Synthesis Using Fluorous Methods
Fluorous Supports Award Winning Research
One of the best applications of fluorous synthesis and purification methods has been in carbohydrate chemistry. This could not be illustrated better than at this year’s Fall ACS National Meeting. The Carbohydrate Division annually bestows three awards at the Fall ACS Meeting; The Wolfrom Award for outstanding service to the Carbohyrate Division and to the field of carbohydrate chemistry, the Isbell Award for excellence in carbohydrate research for researchers under the age of 41, and the New Investigator Award for outstanding contribution from researchers in their first independent faculty position. This year’s awardees include Prof. Robert Linhardt (Rennselear Polytechnic Institute), Prof. Nicola Pohl (Iowa State University), and Prof. Peter Andreana (Wayne State University). Profs. Linhardt and Pohl will each present research using fluorous chemistry.
Fluorous Disaccharides in Enzymatic Synthesis
Prof. Linhardt’s award address will describe his research efforts in heparin analysis and synthesis, including efforts directed toward large-scale enzymatic synthesis. A poster from one of his students reports the use of fluorous tagged disaccharides for the enzymatic synthesis of heparin oligosaccharides. As noted in the abstract the purification of heparin is laborious and time-consuming. Just the kind of problem fluorous can solve. This poster can be viewed either at Sci-Mix on Sunday night or at the general poster session on Wednesday evening.
Automated Carbohydrate Synthesis and Oligosaccharide Microarraying for Glycomics
Prof. Pohl’s award address will detail her group’s accomplishments in using fluorous methods for the preparation and arraying of oligosaccharides using fluorous tags. Prof. Pohl has pioneered the use of fluorous tags for automated oligosaccharide synthesis and their immobilization on fluorous modified surfaces. Her research vision is to enable automated synthesis of carbohydrates in order to accelerate glycomics research. Initial efforts using solid phase proved fruitless and she turned to fluorous supported chemistry. Since that time her group has made giant strides in realizing their goal with fluorous chemistry playing a significant role. In addition, a poster will be presented by one of her students reporting recent results using multiple fluorous tags with multiple fluorous domains.
Fluorous Technologies Inc. congratulates each of these individuals for their awards and is proud to see them use fluorous techniques as a part of their award-winning research.
Fluorous Domains in Materials Research
Due to their unique physical and chemical properties, fluorous chains have found use in a variety of material applications. The hydrophobic and lipophobic nature of fluorous domains leads to unique physical properties while the electron withdrawing effects of fluorous chains can lead to interesting chemical properties.
Fluorous Surfaces in Microfluidics
Results to be reported by Prof. Hugh Horton (Queen’s University) show that fluorous modification of oxidized polydimethylsiloxane (PDMS) provides a fluorous surface capable of selectively adsorbing fluorous tagged peptides and proteins. The fluorous PDMS also maintains a significant zeta potential over a wide pH range and is resistant to aging effects which degrade other modified PDMS surfaces. These results indicate fluorous PDMS could be a promising material for microfluidics applications, particularly those using electro-osmotic flow.
Fluorous Materials in Semiconductors
Meanwhile, Prof. Haoran Sun of the University of South Dakota will present some of his group’s latest results on the incorporation of fluorous domains in organic semiconductors. Items mentioned in the abstract include the manipulation of HOMO and LUMO levels and the tuning of optical and electrical properties using perfluoroalkyl substitution on arenes.
For complete list and details, including location and time, for each of the presentations above please see the Fall 2010 ACS Meeting post in F-Blog.
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.
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