title: Synthesis of molecularly encoded oligomers using a chemoselective "AB + CD" iterative approach.
abstract: A library of eight sequence-defined model oligomers, whose sequence is based on a (0,1) binary code, is prepared through chemoselective repeating cycles of amidification and copper-assisted alkyne-azide cycloaddition reactions from a non-modified Wang resin. This library is constructed from two AB (A = acid, B = alkyne) building blocks, i.e., 4-pentynoic acid and 2-methyl-4-pentynoic acid acting, respectively, as non-coding (0) and coding (1) monomer, and 1-amino-11-azido-3,6,9-trioxaundecane as complementary CD (C = amine, D = azide) spacer building block. In particular, encoded triads are synthesized by consecutive covalent attachment of five building blocks (i.e., three coding/non-coding monomers and two spacers). In this communication, optimal protocols for the synthesis of the targeted oligomers are reported along with their full characterization by (1) H NMR, MALDI-TOF mass spectrometry, and size-exclusion chromatography. It is found that all possible encoded triads (i.e., eight possibilities) could be synthesized using this approach. Indeed, monodisperse sequence-defined oligomers are prepared and characterized in all cases.
authors: Precision Macromolecular Chemistry Group, Institut Charles Sadron, CNRS-UPR 22, 23 rue du Loess, 67034, Strasbourg Cedex 2, France.
authors: Thanh Tam
authors: TT
authors: Trinh
authors: Precision Macromolecular Chemistry Group, Institut Charles Sadron, CNRS-UPR 22, 23 rue du Loess, 67034, Strasbourg Cedex 2, France.
authors: Laurence
authors: L
authors: Oswald
authors: Precision Macromolecular Chemistry Group, Institut Charles Sadron, CNRS-UPR 22, 23 rue du Loess, 67034, Strasbourg Cedex 2, France.
authors: Delphine
authors: D
authors: Chan-Seng
authors: Precision Macromolecular Chemistry Group, Institut Charles Sadron, CNRS-UPR 22, 23 rue du Loess, 67034, Strasbourg Cedex 2, France.
authors: Jean-François
authors: JF
authors: Lutz
mesh_terms: D002850:Chromatography, Gel; D009682:Magnetic Resonance Spectroscopy; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
chemical_list: D011108:Polymers
keywords: amidification; copper-assisted alkyne-azide cycloaddition; sequence-controlled oligomers