title: Solid-phase synthesis of asymmetrically branched sequence-defined poly/oligo(amidoamines).
abstract: We present for the first time the synthesis of asymmetrically branched sequence-defined poly/oligo(amidoamines) (PAAs) using solid-phase synthesis with the capability of introducing diversity at the side chains. We introduce two new versatile (diethylenetriamine) building blocks for solid-phase synthesis bearing Fmoc/Boc and Fmoc/Alloc protecting groups expanding recently used Fmoc/Boc protecting group strategy for linear PAAs to an Fmoc/Alloc/Boc strategy. This allows for orthogonal on-resin cleavage of Fmoc and Alloc protecting groups during solid-phase synthesis of PAAs with backbones differing in chain length and sequence. With these structures we then demonstrate the potential for generating asymmetrical branching by automated multiple on-resin cleavage of Alloc protecting groups as well as the introduction of side chains varying in length and number. Such systems have high potential as nonviral vectors for gene delivery and will allow for more detailed studies on the correlation between the degree of branching of PAAs and their resulting biological properties.
authors.affiliation: Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany.
authors.forename: Felix
authors.initials: F
authors.lastname: Wojcik
authors.forename: Simone
authors.initials: S
authors.lastname: Mosca
authors.forename: Laura
authors.initials: L
authors.lastname: Hartmann
mesh_terms: D003959:Diamines / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D011073:Polyamines / Q000737:chemistry*; D060327:Solid-Phase Synthesis Techniques; D013237:Stereoisomerism
chemical_list: D003959:Diamines; C575052:N1-(2-aminoethyl)-N2-tritylethane-1,2-diamine; D011073:Polyamines; C005391:diethylenetriamine