Transcript Automated Carbohydrate Synthesis

Department of Chemistry
Seminar Announcement
Date/Time/Venue
Title/Speaker
10 Feb (Thu)
11am – 12nn
Automated Carbohydrate Synthesis
@ S8 Level 3
Executive
Classroom
Professor Peter H Seeberger
Max-Planck Institute for Colloids and Surfaces &
Free University of Berlin, Germany
Host : Assoc Prof Tan Choon Hong
About the Speaker
Professor Peter H. Seeberger received his Vordiplom in 1989 from the
Universität Erlangen-Nürnberg. In 1995 he earned his Ph.D. from the
University of Colorado. After a postdoctoral fellowship at the SloanKettering Institute for Cancer Research in New York, he became
Assistant Professor at the Massachusetts Institute of Technology in
January 1998 and was promoted to Firmenich Associate Professor of
Chemistry in 2002. From June 2003 until January 2009, he held the
position of Professor for Organic Chemistry at the Swiss Federal
Institute of Technology (ETH) in Zurich. In 2009, he assumed position
as Director at the Max-Planck Institute for Colloids and Surfaces in
Potsdam and Professor at the Free University of Berlin. He serves as an Affiliate Professor
at the Sanford-Burnham Institute in La Jolla, CA. Prof Seeberger was awarded the
Tetrahedron Young Investigator Award 2010 for Bioorganic and Medicinal Chemistry.
Abstract
Carbohydrates on the surface of cells are involved in a host of fundamental biological processes.1
While peptides and oligonucleotides are now readily accessible using automated solid phase
synthesis, access to complex carbohydrates has been very difficult and time consuming. Described is
the development of a fully integrated platform based on automated oligosacharide synthesis2,3,4 and
carbohydrate arrays to address biological problems. Particular emphasis will be placed on the latest
verison of the automated synthesis platform that is currently being made available to laboratories
around the world.
Bioinformatics studies have revealed that a relatively small number of building blocks is required to
synthesize a large portion of the occupied glycospace.5,6 Automated oligosaccharide synthesis relies
on access to usable quantities of monosaccharide building blocks. In order to shorten synthetic
routes, we have designed de novo methods using purely chemical4 as well as enzymatic means. 7
The synthesis of glycosaminoglycans, a highly complex class of carbohydrates that includes heparin,
is even more complex as it requires the sulfation at particular positions. For that purpose a new
strategy and a new instrument had to be designed that now yields glycosaminoglycan
oligosaccharides in days rather than months.8
1. Seeberger, P.H.; Nature 2005, 437, 1239.
2. Plante, O.J.; Palmacci, E.R.; Seeberger, P.H.; Science 2001, 291, 1523.
3. Seeberger, P.H.; Werz, D.B.; Nature 2007, 446, 1046
4. Seeberger, P.H.; Kröck, L.; Esposito, D.; Wang, C.-C.; Bindschädler, P.; Castagner, B.; submitted.
5. Werz, D.B.; Ranzinger, R.; Herget, S.; Adibekian, A.; von der Lieth, C.-W.; Seeberger, P.H.; ACS Chem. Biol., 2007, 2,
685
6. Adibekian, A.; Stallforth, P.; Hecht, L.-M.; Werz, D.B.; Gagneux, P.; Seeberger, P.H.; Chem. Sci., 2010, 1, in press.
7. Timmer, M.S.M.; Adibekian, A.; Seeberger, P.H. Angew. Chem.Int. Ed. 2005, 44, 7605.
6. Gillingham, D.G.; Stallforth, P.; Adibekian, A.; Seeberger, P.H.; Hilvert, D.; Nature Chemistry, 2010, 2, 102.
8. Eller, S.; Jin, Y.; Hahm; Collot, M.; Klein, J.C. in preparation
All are Welcome