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. 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

Grant R Krow  1 , 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
Affiliations

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

Grant R Krow et al. Org Lett. .

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.

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Figures

Figure 1
Figure 1
CD spectra for (A) 100 μM of NBOC-(MPCA)n-OMe in methanol (25 °C). (B) 100 μM of octamer 16a in water, nPrOH, and mixtures of water/nPrOH (25 °C). Data are normalized for β-peptide concentration and number of amides.
Figure 2
Figure 2
(Top) ORTEP drawing of tetramer 14a. (Bottom) Spartan MMFF minimized (T4)n conformer of tetramer 14a.
See this image and copyright information in PMC

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