Secondary structural preferences of 2,2-disubstituted pyrrolidine-4-carboxylic acid oligomers: beta-peptide foldamers that cannot form internal hydrogen bonds

Journal of the American Chemical Society
Bayard R HuckS H Gellman

Abstract

We examine a new class of beta-peptides, 2,2-disubstituted pyrrolidine-4-carboxylic acid oligomers, and show that they manifest discrete conformational preferences despite the impossibility of internal hydrogen bonding. Numerous beta-peptide families have been described that display specific secondary structural preferences, but all of the conformations characterized in detail so far have contained internal hydrogen bonds. Internal hydrogen bonding is observed within the most common secondary structures of conventional peptides as well. Identifying foldamers in which shape control is independent of hydrogen bonding is significant in two ways. At a fundamental level, foldamers in this small but growing class are interesting because their shapes are controlled by distinctive networks of noncovalent forces. At a practical level, non-hydrogen bonded foldamers may be useful in biomedical applications because the low intrinsic polarity of their backbones may promote bioavailability.

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Citations

Oct 27, 2004·Proteins·Haizhen Zhong, Heather A Carlson
Nov 4, 2010·Organic Letters·Grant R KrowRonald T Raines
Mar 1, 2006·International Journal of Peptide Research and Therapeutics·Peter M Fischer
Feb 23, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Céline MothesPhilippe Karoyan
Aug 18, 2004·Current Opinion in Structural Biology·Richard P Cheng
Jul 29, 2004·Organic & Biomolecular Chemistry·Gianluigi LuppiClaudia Tomasini
Aug 2, 2012·Chemical Communications : Chem Comm·Gowri PriyaGangadhar J Sanjayan
Dec 25, 2010·Biopolymers·Christian A Olsen
Jun 3, 2015·Chemistry, an Asian Journal·Yu HaoDan Yang
Apr 3, 2020·Chirality·Yuko OtaniTomohiko Ohwada
May 9, 2014·The Journal of Organic Chemistry·Juliette FremauxGilles Guichard
Jan 16, 2018·The Journal of Organic Chemistry·Hina P A Khan, Tushar Kanti Chakraborty
Dec 18, 2003·Journal of the American Chemical Society·Leah M Sandvoss, Heather A Carlson
Feb 16, 2006·Journal of the American Chemical Society·Claudia TomasiniMagda Monari

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