Structural Properties and Stereochemically Distinct Folding Preferences of 4,5-cis and trans-Methano-L-Proline Oligomers: The Shortest Crystalline PPII-Type Helical Proline-Derived Tetramer

Angewandte Chemie
Gilles BergerStephen Hanessian

Abstract

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 polyproline II 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→π* stabilization of the trans-amide conformation.

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Citations

Dec 14, 2016·Organic & Biomolecular Chemistry·Vladimir Kubyshkin, Nediljko Budisa
Oct 25, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Lorenzo BiancalanaGuido Pampaloni
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Jun 25, 2016·Beilstein Journal of Organic Chemistry·Vladimir Kubyshkin, Nediljko Budisa
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Feb 27, 2020·The Journal of Organic Chemistry·Yassin M ElbatrawiJuan R Del Valle
Sep 9, 2017·Accounts of Chemical Research·Stefanie DobitzHelma Wennemers

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