Clay S. Bennett

Clay S. Bennett

Professor
617-627-0621
Pearson Chemical Laboratory
62 Talbot Avenue, Medford, MA

Education

  • Ruth L. Kirschstein NRSA Postdoc Fellow, Scripps Research Institute, San Diego, CA, 2005-08,
  • PhD, University of Pennsylvania, Philadelphia, PA, 2005
  • BA, Connecticut College, New London, CT, 1999

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 Publications and Presentations

"Reagent Controlled α-Selective Dehydrative Glycosylations of 2,6-Dideoxy- and 2,3,6-Trideoxy-Sugars” Nogueira, J. N.; Bylsma, M.; Bright, D. K.; Bennett, C. S., Angew. Chem. Int. Ed. 2016, 55, 10088-10092.

"A Convenient Synthesis of di-O¬Acetyl-D-Rhanmal (di-O-Acetyl-6-Deoxy-Glucose)", Spradlin, J. N. Lloyd, D.; Bennett, C. S. Carbohydrate Chemistry: Proven Synthetic Methods, vol. 4 Accepted manuscript.

"Aryl(trifluoroethyl)iodonium Triflimide and Nitrile Solvent Systems: A Combination for the Stereoselective Synthesis of Armed 1,2-trans--Glycosides at Noncryogenic Temperatures", Chu, A.-H. A.; Minciunescu, A.; Bennett, C. S. Org. Lett. 2015, 16, 6262-6265.

“A Gram-Scale Synthesis of an Armed Colitose Donor”, Lloyd, D., Bennett, C. S. J. Org. Chem. 2014, 79, 9826-9829.

“Matched/Mismatched Interactions in Chiral Brønsted Acid Catalyzed Glycosylation Reactions with 2-Deoxy-Sugar Trichloroacetimidate Donors”, Liu, D.; Sarrafpour, S.; Guo, W.; Goulart, B.; Bennett, C. S. J. Carbohydr. Chem. 2014, 33, 423-434.

“A Reagent Controlled SN2-Glycosylation for the Direct Synthesis of β-Linked 2-Deoxy-Sugars”, Issa, J. P.; Bennett, C. S. J. Am. Chem. Soc. 2014, 136, 5740-5744.

“An Air- and Water-Stable Iodonium Salt Promoter for Facile Thioglycoside Activation”, Chu, A.-H. A.; Minciunescu, A.; Montanari, V.; Kumar, K.; Bennett, C. S. Org. Lett. 2014, 16, 1780-1782.

“Principles of Modern Solid-Phase Oligosaccharide Synthesis”, Bennett, C. S. Org. Biol. Mol. Chem. 2014, 12, 1686-1698. (Invited Review)

“Reagent Controlled b-Specific Dehydrative Glycosylation Reactions with 2-Deoxy-Sugars”, Issa, J. P.; Lloyd, D.; Steliotes, E.; Bennett, C. S. Org. Lett. 2013, 15, 4170-4173.

“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. 2013, 15, 2566-2569.

“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.