Synthesis and biological evaluation of hydrogen-bond surrogate based artificial alpha-helices

ORGN 411

Deyun Wang, dw522@nyu.edu, Gianluca Dimartino, gd31@nyu.edu, and Paramjit S. Arora, arora@nyu.edu. Department of Chemistry, New York University, 100 Washington Square East, New York, NY 10003
We recently described a new approach for the stabilization of artificial alpha-helices that involves replacement of one of the main chain hydrogen bonds with a carbon-carbon bond derived from a ring-closing metathesis reaction. The salient feature of this hydrogen-bond surrogate (HBS) approach is that it affords constrained alpha-helices without restricting access to the molecular recognition surfaces or altering the side chain functionalities. We have found that these HBS alpha-helices can target chosen protein receptor with high affinity. This poster will discuss the relationship between macrocycle structure and helicity, and regulation of apoptosis by these artificial helices.

 

New Reactions and Methodology, Bioorganic Chemistry, Molecular Recognition and Self Assembly
8:00 PM-10:00 PM, Tuesday, 28 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- Ex. Hall B4, Sci-Mix

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006