Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 45, Pages 13268-13272Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201506208
Keywords
circular dichroism; methanoproline; natural bond orbitals; polyproline
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Funding
- NSERC
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The synthesis, structural properties, and folding patterns of a series of L-proline methanologues represented by cis- and trans-4,5-methano-L-proline amides and their oligomers are reported as revealed by X-ray crystallography, circular dichroism measurements, and DFT calculations. We disclose the first example of a crystalline tetrameric proline congener to exhibit a polyprolineII helical conformation. Experimental evidence of PPII-type helical arrangement (both in solution and in the solid state) of cis-4,5-methano-L-proline oligomers is supported by theoretical calculations reflecting the extent of n* stabilization of the trans-amide conformation.
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