Faculty


Bennett

Clay S. Bennett

Department of Chemistry
Pearson Chemistry Laboratory
62 Talbot Avenue
Tufts University 
Medford, MA 02155 

Office: P-305A

Tel: 617-627-0621  Fax: 617-627-3443

E-mail:clay.bennett@tufts.edu 

Research Homepage


Current Appointment

 

Assistant Professor of Chemistry, Department of Chemistry

 

Education

 

Ruth L. Kirschstein NRSA Postdoc Fellow, 2005-08, Scripps Research Institute, San Diego, CA

Ph.D., 2005, University of Pennsylvania, Philadelphia, PA

B.A., 1999, Connecticut College, New London, CT

 

Research Interests


Chemistry and Chemical Biology of Carbohydrates.  Complex carbohydrates play critical roles in a number of biological processes including, protein folding, cellular adhesion and signaling. Despite their importance, very little is understood about the molecular basis of their activity. This is largely due to the fact that the only source of pure oligosaccharides is tedious multi-step synthesis, which can take months or even years to compete. Our research is focused on developing methodologies, based on asymmetric catalysis, to streamline complex oligosaccharide synthesis. Ultimately such methods will aid in the rapid and routine preparation of oligosaccharides for biophysical studies and drug discovery.

 

Selected Recent Publications


“Selective Synthesis of 1,2-cis-Glycosides Without Directing Groups. Application to Iterative Oligosaccharide Synthesis”, Chu, A.-H. A.; Nguyen, S. H.; Sisel, J. R.; Minciunescu, A.; Bennett, C. S. Org. Lett. DOI: 10.1021/ol401095k

 

“Halide Effects on Cyclopropenium Cation Promoted Dehydrative Glycosylation with Deoxy-Sugars: Highly alpha-Selective Glycosylations using a 3,3-Dibromo-1,2-diphenylcyclopropene Promoter”, Nogueira, J. M.; Issa, J. P.; Chu, A.-H.; Sisel, J. R.; Schum, R. S.; Bennett, C. S. Eur. J. Org. Chem. 2012, 4927-4930.

 

“3,3-dichloro-1,2-diphenylcyclopropene, CAS No: 2570-00-5 (2012)”, Bennett, C. S. Encyclopedia of Reagents for Organic Synthesis [Online], John Wiley & Sons Ltd., DOI: 10.1002/047084289X.r01514.

 

“Direct O-Glycosidation of Resin Bound Thioglycosides”, Nguyen, S. H.; Trotta, A.; Cao. J.; Straub, T. J.; Bennett, C. S. Org. Biomol. Chem. 2012, 10, 2373-2375.

 

“Cyclopropenium Cation-Promoted Dehydrative GLycosylations Using 2-Deoxy and 2,6-Dideoxy-Sugars” Nogueira, J. M.; Nguyem, S. N. Bennett, C. S. Org. Lett. 2011, 13, 2814-2817

 

“Design, Synthesis, and Biological Evaluation of EF- and ABEF- Analoques of (+)-Spongistatin 1” Smith, A. B., III; Risatti, C. A.; Atasoylu, O.; Bennett, C. S.; TenDyke, K.; Xu, Q. Org. Lett. 2010, 12, 1792-1795.

 

"Chemoenzymatic Elaboration of Monosaccharides Using Engineered Cytochrome P450BM3 Demethylases", J. C. Lewis, S. Bastian, C. S. Bennett, Y. Fu, Y. Mitsuda, M. M. Chen,
W. A. Greenberg, C. H. Wong, and F. H. Arnold, Proc. Natl. Acad. Sci. USA, 2009, 106, 16550-55.

 

"Spongipyran Synthetic Studies. Evolution of a Scalable Total Synthesis of (+)-Spongistatin 1",
A. B. Smith, C. Sfouggatakis, C. A. Risatti, J. B. Sperry, W. Zhu, V. A. Doughty, T. Tomioka, D. B. Gotchev, C. S. Bennett, S. Sakamoto, O. Atasoylu, S. Shirakami, D. Bauer, M. Takeuchi, J.  Koyanagi, Y. Sakamoto, Tetrahedron, 2009, 65, 6489-6509

 

"Sugar-Assisted Glycopeptide Ligation with Complex Oligosaccharides: Scope and Limitations",
C. S. Bennett, S. M. Dean, R. J. Payne, S. Ficht, A. Brik and C-H. Wong,  J. Am. Chem. Soc. 2008, 130, 11945-52.

 

"Chemoenzymatic Approaches to Glycoprotein Synthesis", C. S. Bennett and C-H. Wong, Chem. Soc. Rev. 2007, 36, 1227-1238.

 

"Sugar-Assisted Ligation (SAL) of N-Linked Glycopeptides with Broad Sequence Tolerance at the Ligation Junction", A. Brik, S. Ficht, Y-Y. Yang, C. S. Bennett and C-H. Wong, J. Am. Chem. Soc. 2006, 128, 15026-15033.

 

"Advances in Glycoprotein Synthesis", L. Lui, C. S. Bennett and C-H. Wong, Chem. Commun.
2006
, 21-33.