ORGN 594 |
| Oligo-N-substituted glycine (peptoid) scaffolds were used as substrates for azide-alkyne [3+2]-cycloaddition reactions and then elaborated through additional rounds of oligomerization and cycloaddition. We demonstrate that the 1,2,3-triazole linkages of these Click Chemistry reactions are fully compatible with standard peptoid “submonomer” synthesis protocols on solid-phase support. Up to four complete cycles of “sequential click chemistry” were conducted in high yield, generating dodecamers functionalized with four distinct side-chain conjugates. This technique will allow for the generation of complex peptidomimetic products in which multiple heterogeneous pendant groups are site-specifically positioned along the oligomer scaffold.
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Asymmetric Reactions, Heterocycles, Aromatics, Combinatorial, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 31 August 2005 Washington DC Convention Center -- Hall A, Poster
Division of Organic Chemistry |
