title: Sulfono-γ-AApeptides as a new class of nonnatural helical foldamer.
abstract: Foldamers offer an attractive opportunity for the design of novel molecules that mimic the structures and functions of proteins and enzymes including biocatalysis and biomolecular recognition. Herein we report a new class of nonnatural helical sulfono-γ-AApeptide foldamers of varying lengths. The crystal structure of the sulfono-γ-AApeptide monomer S6 illustrates the intrinsic folding propensity of sulfono-γ-AApeptides, which likely originates from the bulkiness of tertiary sulfonamide moiety. The two-dimensional solution NMR spectroscopy data for the longest sequence S1 demonstrates a 10/16 right-handed helical structure. Optical analysis using circular dichroism further supports well- defined helical conformation of sulfono-γ-AApeptides in solution containing as few as five building blocks. Future development of sulfono-γ-AApeptides may lead to new foldamers with discrete functions, enabling expanded application in chemical biology and biomedical sciences.
authors.affiliation: Department of Chemistry, University of South Florida, 4202 E. Fowler Ave, Tampa, FL 33620 (USA).
authors.forename: Haifan
authors.initials: H
authors.lastname: Wu
authors.forename: Qiao
authors.initials: Q
authors.lastname: Qiao
authors.forename: Yaogang
authors.initials: Y
authors.lastname: Hu
authors.forename: Peng
authors.initials: P
authors.lastname: Teng
authors.forename: Wenyang
authors.initials: W
authors.lastname: Gao
authors.forename: Xiaobing
authors.initials: X
authors.lastname: Zuo
authors.forename: Lukasz
authors.initials: L
authors.lastname: Wojtas
authors.forename: Randy W
authors.initials: RW
authors.lastname: Larsen
authors.forename: Shengqian
authors.initials: S
authors.lastname: Ma
authors.forename: Jianfeng
authors.initials: J
authors.lastname: Cai
mesh_terms: D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D057786:Peptidomimetics; D017433:Protein Structure, Secondary; D017434:Protein Structure, Tertiary; D013450:Sulfones / Q000737:chemistry*
chemical_list: D010455:Peptides; D057786:Peptidomimetics; D013450:Sulfones
keywords: 2D NMR spectroscopy; X-ray crystal structure; helical foldamer; peptidomimetics; sulfono-γ-AApeptides