Synthesis of cyclic peptidomimetics inspired by γ-turns and applications to library design

ORGN 819

Erik Fenster, efenster@ku.edu, The Center for Chemical Methodology and Library Development at the University of Kansas, University of Kansas, 1501 Wakarusa Drive, Lawrence, KS 66047 and Jeffrey Aubé, jaube@ku.edu, Department of Medicinal Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Room 4070, Malott Hall, Lawrence, KS 66045-7582.
A series of peptidomimetics based on a γ-turn motif were prepared, in which N-substituted piperidones were reacted with a selection of 2-hydroxyalkyl azides derived from common L-amino acids. A variety of nucleophiles were found to add at the distal ether carbon in the initially formed iminium ethers rather than the more electrophilic oxazolinium carbon. This consequence was exploited such that a series of diversely substituted 1,4-diazepinones were prepared. The applicability of this chemistry to the construction of 1,4-diazepinone libraries has also been investigated.

 

Combinatorial, Parallel and Process Chemistry, Heterocycles, Aromatics, New Reactions and Methodology
8:00 PM-10:00 PM, Wednesday, August 22, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007