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

ABSTRACT: 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.

SUBMITTER: Krow GR 

PROVIDER: S-EPMC2993784 | biostudies-literature | 2010 Dec

REPOSITORIES: biostudies-literature