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

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

Author information

1
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. grkrow@temple.edu

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.

PMID:
21043445
PMCID:
PMC2993784
DOI:
10.1021/ol1022917
[Indexed for MEDLINE]
Free PMC Article

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