ORGN 324 |
| Oligomers of N-substituted glycine, or peptoids, are known to be capable of adopting stable secondary structures. We have established two strategies for macrocyclization of peptoid sequences that provide enhanced conformational ordering of the products. One strategy involves solid phase Cu(I)-catalyzed [3+2] cycloaddition reactions between azide and alkyne sidechains pre-organized on the face of a peptoid helix. We also demonstrate the head-to-tail cyclization of peptoid C-terminal acids by amide bond formation. These macrocyclization reactions proceed with remarkable efficiency for a variety of sequences and chain lengths. X-ray crystallography of the cyclic peptoids allows an evaluation of the structural consequences upon establishing the covalent constraints.
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Molecular Recognition and Self-Assembly
1:00 PM-5:00 PM, Monday, 11 September 2006 Moscone Center -- Room 132, Oral
Division of Organic Chemistry |
