title: Diaminodiacid-based solid-phase synthesis of all-hydrocarbon stapled α-helical peptides.
abstract: An alternative stapling strategy is described herein using Fmoc-solid phase peptide synthesis (SPPS) that employed pre-prepared diaminodiacid building blocks to introduce all-hydrocarbon staples into peptides by on-resin cyclization. Compared to unstapled native peptides, diaminodiacid-based stapled peptides exhibited an increased α-helicity ratio and stability toward protease. Moreover, the linkage length was found to affect the bioactivity of the peptides and their ability to inhibit the Wnt pathway. Therefore, the new stapling method provides an alternative way to obtain stapled peptides with tunable linkers of diaminodiacids.
authors.affiliation: Department of Chemistry, University of Science and Technology of China, Hefei 230026, China. shijing@ustc.edu.cn.
authors.forename: Feng-Liang
authors.initials: FL
authors.lastname: Wang
authors.forename: Ye
authors.initials: Y
authors.lastname: Guo
authors.forename: Si-Jian
authors.initials: SJ
authors.lastname: Li
authors.forename: Qing-Xiang
authors.initials: QX
authors.lastname: Guo
authors.forename: Jing
authors.initials: J
authors.lastname: Shi
authors.forename: Yi-Ming
authors.initials: YM
authors.lastname: Li
mesh_terms: D000599:Amino Acids, Diamino / Q000737:chemistry*; D008968:Molecular Conformation; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000599:Amino Acids, Diamino; D010455:Peptides