Synthesis of a pipecolic acid-based bis-amino acid and its assembly into a spiro ladder oligomer.
[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.
Department of Chemistry, University of Pittsburgh, Pennsylvania 15260, USA.
Sharad
S
Gupta
Bhaskar C
BC
Das
Christian E
CE
Schafmeister
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010875:Pipecolic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D011487:Protein Conformation; D013237:Stereoisomerism
D000596:Amino Acids; D010875:Pipecolic Acids; C031345:pipecolic acid