title: Synthesis of water-soluble scaffolds for peptide cyclization, labeling, and ligation.
abstract: The synthesis and applications of water-soluble scaffolds that conformationally constrain side chain unprotected linear peptides containing two cysteines are described. These scaffolds contain a functionality with orthogonal reactivity to be used for labeling and ligation. This is illustrated by the chemical ligation of two dissimilar constrained peptides via oxime ligation or strain-promoted azide-alkyne cycloaddition in aqueous media.
authors.affiliation: Van't Hoff Institute for Molecular Sciences, University of Amsterdam, Science Park 904, 1098 XH Amsterdam, The Netherlands.
authors.forename: Linde E J
authors.initials: LE
authors.lastname: Smeenk
authors.forename: Nicolas
authors.initials: N
authors.lastname: Dailly
authors.forename: Henk
authors.initials: H
authors.lastname: Hiemstra
authors.forename: Jan H
authors.initials: JH
authors.lastname: van Maarseveen
authors.forename: Peter
authors.initials: P
authors.lastname: Timmerman
mesh_terms: D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D003500:Cyclization; D007700:Kinetics; D015394:Molecular Structure; D010091:Oximes / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis*; D012995:Solubility; D014867:Water / Q000737:chemistry*
chemical_list: D000480:Alkynes; D001386:Azides; D010091:Oximes; D010456:Peptides, Cyclic; D014867:Water