Youssef Itab, Samokhvalova Svetlana, Sergent Isaure, Charles Laurence, Lutz Jean-François
Université de Strasbourg, CNRS, ISIS, 8 allée Gaspard Monge, 67000 Strasbourg, France.
Université de Strasbourg, CNRS, Institut Charles Sadron UPR22, 23 rue du Loess, 67034 Cedex 2 Strasbourg, France.
Precis Chem. 2023 Oct 8;1(8):480-484. doi: 10.1021/prechem.3c00077. eCollection 2023 Oct 23.
Sequence-defined oligocarbamates were synthesized by orthogonal iterative chemistry on a modified Wang solid support. In this approach, amino alcohol building blocks, containing either primary or secondary amines, were used in order to obtain on-demand either a classical urethane motif -NH-CO-O- or a N-substituted urethane linkage -NR-CO-O-. Hence, aperiodic carbamate sequences could be easily prepared in this work. Polymers with different monomer sequences and chain-length were synthesized. Characterization by NMR, SEC and ESI-MS indicated formation of near-monodisperse polymers. Furthermore, these informational oligocarbamates were sequenced by MS/MS. Very interestingly, it was found that a fully orthogonal fragmentation of -NH-CO-O- urethane motifs occurs in these macromolecules.
通过在修饰的Wang固相载体上进行正交迭代化学合成了序列定义的低聚氨基甲酸酯。在这种方法中，使用含有伯胺或仲胺的氨基醇结构单元，以便按需获得经典的氨基甲酸酯基序-NH-CO-O-或N-取代的氨基甲酸酯键-NR-CO-O-。因此，在这项工作中可以轻松制备非周期性的氨基甲酸酯序列。合成了具有不同单体序列和链长的聚合物。通过NMR、SEC和ESI-MS表征表明形成了近单分散聚合物。此外，这些信息性低聚氨基甲酸酯通过MS/MS进行测序。非常有趣的是，发现在这些大分子中发生了-NH-CO-O-氨基甲酸酯基序的完全正交断裂。
