title: Synthesis of the TACO scaffold as a new selectively deprotectable conformationally restricted triazacyclophane based scaffold.
abstract: The synthesis of a new triazacyclophane scaffold (TACO scaffold) containing three selectively deprotectable amines is described. The TACO scaffold is conformationally more constrained than our frequently used TAC scaffold, due to introduction of a substituent on the para position of the benzoic acid hinge, which prevents ring flipping and makes it more attractive than the TAC scaffold for preparation of artificial receptor molecules or for mimicking discontinuous epitopes toward protein mimics when more preorganization is required.
authors.affiliation: Medicinal Chemistry and Chemical Biology, Utrecht Institute for Pharmaceutical Sciences, Faculty of Science, Utrecht University , P.O. Box 80082, 3508 TB Utrecht, The Netherlands.
authors.forename: Arwin J
authors.initials: AJ
authors.lastname: Brouwer
authors.forename: Helmus
authors.initials: H
authors.lastname: van de Langemheen
authors.forename: Adriano
authors.initials: A
authors.lastname: Ciaffoni
authors.forename: Kitty E
authors.initials: KE
authors.lastname: Schilder
authors.forename: Rob M J
authors.initials: RM
authors.lastname: Liskamp
mesh_terms: D000588:Amines / Q000737:chemistry*; D000595:Amino Acid Sequence; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000737:chemistry*; D011506:Proteins / Q000737:chemistry*; D018000:Receptors, Peptide / Q000737:chemistry*
chemical_list: D000588:Amines; D001372:Aza Compounds; D006574:Heterocyclic Compounds, 2-Ring; D010456:Peptides, Cyclic; D011506:Proteins; D018000:Receptors, Peptide; C539946:triazacyclophane