Oligomers of a 5-carboxy-methanopyrrolidine β-amino acid. A search for order

Org Lett. 2010 Dec 3;12(23):5438-41. doi: 10.1021/ol1022917. Epub 2010 Nov 2.


CD spectra for homooligomers (n = 4, 6, 8) of (1S,4R,5R)-5-syn-carboxy-2-azabicyclo[2.1.1]hexane (MPCA), a methano-bridged pyrrolidine β-carboxylic acid, suggest an ordered secondary structure. Even in the absence of internal hydrogen bonding, solution NMR, X-ray, and in silico analyses of the tetramer are indicative of conformations with trans-amides and C(5)-amide-carbonyls oriented toward the C(4) bridgehead. This highly constrained β-amino acid could prove useful in the ongoing development of well-defined foldamers.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amino Acids / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Pyrrolidines / chemistry*


  • Amino Acids
  • Pyrrolidines