March 2009 Technical Newsletter
March 2009 Fluorous Technical Newsletter
CEOverture…
Dear Reader,
Later this month over 10,000 people are expected to convene in Salt Lake City for the semi-annual meeting of America’s largest scientific society- the American Chemical Society. These meetings are a great opportunity for exchange and our VP of Technology, Dr. Marvin Yu, will be attending and presenting. If you would like to meet with Marvin to discuss any aspect of fluorous technology while at the meeting, just drop us a line and we’ll make the arrangements. As anyone who has ever known Marvin will tell you, the conversation is guaranteed to be interesting regardless of the topic. Lots more details about the presence of fluorous technology at the ACS meeting below, so be sure to check out the rest of this month’s newsletter.
Cheers,
Phil
Fluorous Chemistry at the Spring American Chemical Society Meeting in Salt Lake City
This year, the Spring ACS Meeting will be held in Salt Lake City, Utah, March 22-26. The full technical program has been published and is available online. A search of the program yielded about a dozen presentations and posters which highlight fluorous chemistry. We have posted a list of those presentations here.
Of course, this does not include those presentations and posters where fluorous techniques are employed, but not mentioned in either the title of the abstract. If you are using fluorous techniques in your research and presenting at the ACS meeting, please contact us and we will be happy to add your presentation to our list.
Among the presentations to be made in Salt Lake City are the four below.
Fluorous Liquid-Liquid Extraction
Solvent tuning in fluorous extractions: Increasing separation efficiency while lowering fluorine content (BGHT)
Session:ACS Award in Industrial Chemistry: Symposium in Honor of George G. I. Moore
Time: 1:25 PM-4:35 PM, Monday, March 23, 2009
Authors: Marvin S. Yu1, Tadamichi Nagashima1, Qianli Chu2, and Dennis Curran2. (1) Fluorous Technologies Inc. (2) Dept. of Chemistry, University of Pittsburgh
Abstract: Fluorous liquid-liquid extraction has been dubbed a “heavy” fluorous technique due to the high fluorine content necessary to obtain efficient separation. This has limited the use of fluorous separations and biphasic catalysis in industrial applications due to higher cost and environmental concerns. Our research was aimed to developing new fluorous extraction methods which would reduce cost and potential environmental impact. This work has led to a solvent tuning approach based on a qualitative model designed to guide solvent selection. Examples of dramatic increases in fluorous partitioning will be provided along with an application to small molecule synthesis using fluorous biphasic catalysis in solvent tuning principles.
Fluorous Surfactants in Chemical Biology
Synthesis of hybrid fluorous surfactants and their application as additives for protein renaturation (BIOL 222)
Session:Frontiers in Chemical Biology
Time:1:30 PM-4:50 PM, Wednesday, March 25, 2009
Authors: Rajni Singh and Robert A. Flowers II, Department of Chemistry, Lehigh University, 6 E. Packer Avenue, Bethlehem, PA 18015
Abstract: During the course of our studies with fluorous surfactants, it was discovered that fluorous hybrid detergents show promise as refolding reagents for denatured proteins. To begin to understand this phenomenon, preliminary refolding studies were performed on chemically and thermally denatured bovine carbonic anhydrase (CAB) using a series of hemifluorinated surfactants containing a sulfonate head group. Preliminary data shows that these surfactants provide good refolding yields at low as well as high concentrations of CAB compared to their hydrocarbon analogs. In contrast to traditional surfactants, we discovered that hybrid fluorous surfactants are most efficient at concentrations well below their critical micelle concentrations. This talk will present the synthesis and characterization of various hybrid fluorous surfactants and their utility in the renaturation of various structurally different proteins. The relationship between surfactant structure and efficiency in renaturation will also be discussed.
Fluorous Carbohydrate Synthesis
Automated solution-phase synthesis of beta-mannosides (CARB 109)
Session:General Papers
Time:1:20 PM-4:40 PM, Thursday, March 26, 2009
Authors: Shu-Lun Tang and Nicola L. Pohl, Department of Chemistry, Iowa State University, 2606 Gilman Hall, Ames, IA 50010
Abstract: An automated solution-phase oligosaccharide synthesis that relies on a reducing end C8F17 tail for FSPE (Fluorous Solid Phase Extraction) purification provides a more economical method to make complex carbohydrates compared to automated solid-phase protocols. The stereocontrol of the anomeric center is particularly difficult in the formation of beta-mannose linkages in which both neighboring group participation and thermodynamic control favor the alpha-linkage. Herein we present two different strategies for the automated solution-phase synthesis of beta-linked mannose polymers. First, we have developed the first automated protocol to form the beta-linkage through glycosylation of glucose followed by an oxidation/reduction strategy to invert the 2-OH to the mannose configuration. Second, a completely new strategy relies on stereocontrol of the glycosylation of mannuronic acid building blocks, followed by a final global reduction of the esters. These two strategies will be compared and contrasted in the context of the synthesis of fungal- and bacterial-associated oligosaccharides.
Fluorous Labeling of Proteins
Development of a labeling probe for the discovery and identification of saccharide-binding proteins (ORGN 340)
Session:Physical Organic Chemistry, Molecular Recognition, Self-Assembly and Biomolecules
Time: 8:00 PM-10:00 PM, Tuesday, March 24, 2009
Authors: Arun Babu Kumar, Jordan M. Anderson, and Roman Manetsch, Department of Chemistry, University of South Florida, 4202 E Fowler Ave, CHE 205, Tampa, FL 33620
Abstract: Proteins that interact with carbohydrates in a non-covalent fashion occur widely in nature. Such proteins, which have come into the forefront of biological research in recent years, belong to the class of lectins. Herein we introduce a novel class of multifunctional photoaffinity probes, which guarantee the highest possible affinity combined with a straight forward purification procedure by a fluorous tag. We discuss the design, the synthesis and the development of a versatile chemical probe for the selective labeling of carbohydrate-binding proteins. We speculate that our proposed labeling and enrichment protocol has potential to accelerate the discovery and identification of unknown saccharide binding proteins.
ISoFT’09 Call for Papers
If you did not get your paper describing fluorous research submitted in time for the Spring ACS Meeting, you can still submit one for the International Symposium on Fluorous Technologies (ISoFT’09) to be held in beautiful Jackson Hole, Wyoming, Aug 23-28, 2009. Abstract submission is open until April 30th, 2009. Don’t miss your chance to present at a truly exciting conference in a spectacular venue