Origins of the high 14-helix propensity of cyclohexyl-rigidified residues in β-peptides

Myung Ryul Lee, Tami L. Raguse, Marina Schinnerl, William C. Pomerantz, Xiaodong Wang, Peter Wipf, Samuel H. Gellman

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

β-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 conformationpromoting effect, and that polar groups may be attached to the cyclohexyl ring without diminishing the effect.

Original languageEnglish (US)
Pages (from-to)1801-1804
Number of pages4
JournalOrganic Letters
Volume9
Issue number9
DOIs
StatePublished - Apr 26 2007

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Hydrophobic and Hydrophilic Interactions
helices
peptides
Peptides
rings
Population
aqueous solutions
acids
interactions
2-aminocyclohexanecarboxylic acid

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Lee, M. R., Raguse, T. L., Schinnerl, M., Pomerantz, W. C., Wang, X., Wipf, P., & Gellman, S. H. (2007). Origins of the high 14-helix propensity of cyclohexyl-rigidified residues in β-peptides. Organic Letters, 9(9), 1801-1804. https://doi.org/10.1021/ol070511r

Origins of the high 14-helix propensity of cyclohexyl-rigidified residues in β-peptides. / Lee, Myung Ryul; Raguse, Tami L.; Schinnerl, Marina; Pomerantz, William C.; Wang, Xiaodong; Wipf, Peter; Gellman, Samuel H.

In: Organic Letters, Vol. 9, No. 9, 26.04.2007, p. 1801-1804.

Research output: Contribution to journalArticle

Lee, MR, Raguse, TL, Schinnerl, M, Pomerantz, WC, Wang, X, Wipf, P & Gellman, SH 2007, 'Origins of the high 14-helix propensity of cyclohexyl-rigidified residues in β-peptides', Organic Letters, vol. 9, no. 9, pp. 1801-1804. https://doi.org/10.1021/ol070511r
Lee, Myung Ryul ; Raguse, Tami L. ; Schinnerl, Marina ; Pomerantz, William C. ; Wang, Xiaodong ; Wipf, Peter ; Gellman, Samuel H. / Origins of the high 14-helix propensity of cyclohexyl-rigidified residues in β-peptides. In: Organic Letters. 2007 ; Vol. 9, No. 9. pp. 1801-1804.
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