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Org Lett. 2005 Jul 7;7(14):2861-4.

Synthesis of a pipecolic acid-based bis-amino acid and its assembly into a spiro ladder oligomer.

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  • 1Department of Chemistry, University of Pittsburgh, Pennsylvania 15260, USA.


[reaction: see text] The synthesis of a new pipecolic acid-based bis-amino acid building block 1 (and 2) is presented. Assembly of this monomer into a spiro ladder oligomer 3 utilizing solid-phase synthesis followed by in situ activation by dicyclohexylcarbodiimide and N-hydroxysuccinimide has been demonstrated. The structure of oligomer 3, determined in aqueous solution using two-dimensional NMR, reveals that the oligomer forms a left-handed helix and that each monomer unit adopts a chair conformation.

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