title: Dehydrophenylalanine zippers: strong helix-helix clamping through a network of weak interactions.
abstract: A decapeptide Boc-L-Ala-(Delta Delta Phe)(4)-L-Ala-(Delta Delta Phe)3-Gly-OMe (Peptide I) was synthesized to study the preferred screw sense of consecutive alpha,beta-dehydrophenylalanine (Delta Delta Phe) residues. Crystallographic and CD studies suggest that, despite the presence of two L-Ala residues in the sequence, the decapeptide does not have a preferred screw sense. The peptide crystallizes with two conformers per asymmetric unit, one of them a slightly distorted right-handed 3(10)-helix (X) and the other a left-handed 3(10)-helix (Y) with X and Y being antiparallel to each other. An unanticipated and interesting observation is that in the solid state, the two shape-complement molecules self-assemble and interact with an extensive network of C-H...O hydrogen bonds and pi-pi interactions, directed laterally to the helix axis with amazing regularity. Here, we present an atomic resolution picture of the weak interaction mediated mutual recognition of two secondary structural elements and its possible implication in understanding the specific folding of the hydrophobic core of globular proteins and exploitation in future work on de novo design.
authors: Department of Physics and Bioinformatics Center, Indian Institute of Science, Bangalore-560012, India.
authors: Udupi A
authors: UA
authors: Ramagopal
authors: Suryanarayanarao
authors: S
authors: Ramakumar
authors: Puniti
authors: P
authors: Mathur
authors: Ratanmani
authors: R
authors: Joshi
authors: Virander S
authors: VS
authors: Chauhan
mesh_terms: D002942:Circular Dichroism; D003460:Crystallization; D018257:Helix-Loop-Helix Motifs; D006860:Hydrogen Bonding; D008958:Models, Molecular; D010446:Peptide Fragments / Q000737:chemistry* / Q000378:metabolism; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry*; D017433:Protein Structure, Secondary; D012996:Solutions; D012997:Solvents; D013237:Stereoisomerism; D014961:X-Ray Diffraction
chemical_list: D010446:Peptide Fragments; D012996:Solutions; D012997:Solvents; D010649:Phenylalanine; C018632:phenyldehydroalanine