Org. Lett., 9 (9), 1801 -1804, 2007. 10.1021/ol070511r S1523-7060(07)00511-1
Web Release Date: March 30, 2007

Copyright © 2007 American Chemical Society

Origins of the High 14-Helix Propensity of Cyclohexyl-Rigidified Residues in -Peptides

Myung-ryul Lee, Tami L. Raguse, Marina Schinnerl, William C. Pomerantz, Xiaodong Wang, Peter Wipf,* and Samuel H. Gellman*

Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, and Department of Chemistry and Center for Chemical Methodologies and Library Development, University of Pittsburgh, Pittsburgh, Pennsylvania 15260

gellman@chem.wisc.edu; pwipf+@pitt.edu

Received February 28, 2007

Abstract:

-Peptides containing residues derived from trans-2-aminocyclohexanecarboxylic acid (ACHC) display high population of 14-helical secondary structure in aqueous solution. We show that hydrophobic interactions between cyclohexyl rings are not responsible for this conformation-promoting effect, and that polar groups may be attached to the cyclohexyl ring without diminishing the effect.


Download the full text: PDF | HTML