title: Shortcut access to peptidosteroid conjugates: building blocks for solid-phase bile acid scaffold decoration by convergent ligation.
abstract: We present three versatile solid-supported scaffold building blocks based on the (deoxy)cholic acid framework and decorated with handles for further derivatization by modern ligation techniques such as click chemistry, Staudinger ligation or native chemical ligation. Straightforward procedures are presented for the synthesis and analysis of the steroid constructs. These building blocks offer a new, facile and shorter access route to bile acid-peptide conjugates on solid-phase with emphasis on heterodipodal conjugates with defined spatial arrangements. As such, we provide versatile new synthons to the toolbox for bile acid decoration.
authors.affiliation: Laboratory for Organic and Biomimetic Chemistry, Department of Organic Chemistry, Faculty of Sciences, Ghent University, B-9000 Ghent, Belgium.
authors.forename: Dieter
authors.initials: D
authors.lastname: Verzele
authors.forename: Sara
authors.initials: S
authors.lastname: Figaroli
authors.forename: Annemieke
authors.initials: A
authors.lastname: Madder
mesh_terms: D000595:Amino Acid Sequence; D001647:Bile Acids and Salts / Q000138:chemical synthesis* / Q000737:chemistry; D057930:Click Chemistry / Q000379:methods*; D003545:Cysteine / Q000378:metabolism; D052244:Endocrine Disruptors / Q000378:metabolism; D046911:Macromolecular Substances / Q000737:chemistry; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D011956:Receptors, Cell Surface / Q000378:metabolism; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000378:metabolism
chemical_list: D001647:Bile Acids and Salts; D052244:Endocrine Disruptors; D046911:Macromolecular Substances; D010455:Peptides; D011956:Receptors, Cell Surface; D013256:Steroids; D013438:Sulfhydryl Compounds; D003545:Cysteine