NDLI: Engineering a β-Helical d,l-Peptide for Folding in Polar Media

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Engineering a β-Helical d,l-Peptide for Folding in Polar Media

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Engineering a β-Helical d,l-Peptide for Folding in Polar Media

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Kulp, John L. Clark, Thomas D.
Description	Author Affiliation: Kulp JL ( Division of Chemistry, Naval Research Laboratory, Washington, DC 20375-5342, USA.)
Abstract	β Helices—helices formed by alternating d,l-peptides and stabilized by β-sheet hydrogen bonding—are found naturally in only a handful of highly hydrophobic peptides. This paper explores the scope of β-helical structure by presenting the first design and biophysical characterization of a hydrophilic d,l-peptide, 1, that forms a β helix in methanol. The design of 1 is based on the β-hairpin/β helix—a new supersecondary that had been characterized previously only for hydrophobic peptides in nonpolar solvents. Incorporating polar residues in 1 provided solubility in methanol, in which the peptide adopts the expected β-hairpin/β-helical structure, as evidenced by CD, analytical ultracentrifugation (AUC), NMR spectroscopy, and NMR-based structure calculations. Upon titration with water (at constant peptide concentration), the structure in methanol (1 m) transitions cooperatively to an extended conformation (1 w) resembling a cyclic β-hairpin; observation of an isodichroic point in the solvent-dependent CD spectra indicates that this transition is a two-state process. In contrast, neither 1 m nor 1 w show cooperative thermal melting; instead, their structures appear intact at temperatures as high as 65 °C; this observation suggests that steric constraint is dominant in stabilizing these structures. Finally, the $^{1}H NMR$ CαH spectroscopic resonances of 1 m are downfield-shifted with respect to random-coil values, a hitherto unreported property for β helices that appears to be a general feature of these structures. These results show for the first time that an appropriately designed β-helical peptide can fold stably in a polar solvent; furthermore, the structural and spectroscopic data reported should prove useful in the future design and characterization of water-soluble β helices.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	44
Volume Number	15
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2009-11-09
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Drug Design Peptides Chemistry Protein Folding Amino Acid Sequence Circular Dichroism Hydrophobic And Hydrophilic Interactions Magnetic Resonance Spectroscopy Models, Molecular Protein Structure, Secondary Solvents Temperature Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, Non-P.H.S.
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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