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

Grant R Krow; Nian Liu; Matthew Sender; Guoliang Lin; Ryan Centafont; Philip E Sonnet; Charles DeBrosse; Charles W Ross 3rd; Patrick J Carroll; Matthew D Shoulders; Ronald T Raines

doi:10.1021/ol1022917

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.

Authors

Grant R Krow¹, Nian Liu, Matthew Sender, Guoliang Lin, Ryan Centafont, Philip E Sonnet, Charles DeBrosse, Charles W Ross 3rd, Patrick J Carroll, Matthew D Shoulders, Ronald T Raines

Affiliation

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.

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*

Substances

Amino Acids
Pyrrolidines

Abstract

Publication types

MeSH terms

Substances

Grants and funding