Sequencing of Sequence-Defined Oligourethanes via Controlled Self-Immolation
Sequence-defined polymers show promise for biomimetics, self-assembly, catalysis, and information storage, wherein the primary structure begets complex chemical processes. Here we report the solution-phase and the high-yielding solid-phase syntheses of discrete oligourethanes and methods for their s...
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| Veröffentlicht in: | Journal of the American Chemical Society 2020-02, Vol.142 (6), p.2744-2749 |
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| container_title | Journal of the American Chemical Society |
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| creator | Dahlhauser, Samuel D Escamilla, P. Rogelio VandeWalle, Abigail N York, Jordan T Rapagnani, Rachel M Shei, Jasper S Glass, Samuel A Coronado, Jaime N Moor, Sarah R Saunders, Douglas P Anslyn, Eric V |
| description | Sequence-defined polymers show promise for biomimetics, self-assembly, catalysis, and information storage, wherein the primary structure begets complex chemical processes. Here we report the solution-phase and the high-yielding solid-phase syntheses of discrete oligourethanes and methods for their self-immolative sequencing, resulting in rapid and robust characterization of this class of oligomers and polymers, without the use of MS/MS. Crucial to the sequencing is the inherent reactivity of the terminal alcohol to “unzip” the oligomers, in a controlled and iterative fashion, releasing each monomer as a 2-oxazolidinone. By monitoring the self-immolation reaction via LC/MS, an applied algorithm rapidly produces the sequence of the oligourethane. Not only does this process provide characterization of structurally complex molecules, it works as a reader of molecular information. |
| doi_str_mv | 10.1021/jacs.9b12818 |
| format | Article |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Algorithms Chromatography, Liquid - methods Molecular Structure Polymers - chemistry Tandem Mass Spectrometry - methods Urethane - chemistry |
| title | Sequencing of Sequence-Defined Oligourethanes via Controlled Self-Immolation |
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