Maximizing the stereochemical diversity of spiro-ladder oligomers.
[reaction: see text] We introduce all stereoisomers of a bis-amino acid building block derived from trans-4-hydroxy-L-proline. This small library of monomers allows arbitrary stereochemical configuration at any chiral center within our spiro-ladder oligomers. Three tetramer oligomers containing several combinations of the monomers 1-4 were synthesized; we explored the effect of monomer sequence on scaffold conformation by NMR.
Levins
Christopher G
CG
Department of Chemistry, University of Pittsburgh, Pennsylvania 15260, USA.
Brown
Zachary Z
ZZ
Schafmeister
Christian E
CE
D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011108:Polymers / Q000138:chemical synthesis*; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
D011108:Polymers; D011758:Pyrroles; D013141:Spiro Compounds; D011392:Proline