Photocontrolled Synthesis of Abiotic Sequence‐Defined Oligo(Phosphodiester)s,Macromolecular Rapid Communications

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Photocontrolled Synthesis of Abiotic Sequence‐Defined Oligo(Phosphodiester)s
Macromolecular Rapid Communications ( IF 4.2 ) Pub Date : 2017-11-16 , DOI: 10.1002/marc.201700651
Niklas Felix König ₁ , Sofia Telitel ₁ , Salomé Poyer ₂ , Laurence Charles ₂ , Jean-François Lutz ₁

Affiliation

A photoregulated phosphoramidite iterative process is studied for the synthesis of non‐natural, digitally encoded oligo(phosphodiester)s. The oligomers are prepared using two reactive phosphoramidite monomers containing a 2‐(2‐nitrophenyl)propoxycarbonyl (NPPOC) protected OH group. The stepwise synthesis is performed on an OH‐functional soluble polystyrene support, which allows recycling by precipitation in a nonsolvent. Repeating cycles involving phosphoramidite coupling, oxidation of phosphite to phosphate, and NPPOC deprotection by light irradiation at λ = 365 nm are performed in order to prepare oligomers with different lengths and sequences. Synthesis is conducted on a micromolar scale and good recycling yields are obtained in all cases. The use of a soluble polymer support allows an in‐depth characterization of the NPPOC photo‐deprotection step by ¹H NMR, UV spectroscopy, and size exclusion chromatography, and thus identification of optimal synthesis conditions. After cleavage from the support, the oligo(phosphodiester)s are characterized by tandem mass spectrometry, which confirms preparation of uniform sequence‐coded oligomers.

中文翻译：

非生物序列定义的寡聚（磷酸二酯）的光控合成

研究了光调节的亚磷酰胺的迭代过程，用于合成非天然的，数字编码的低聚（磷酸二酯）。该低聚物是使用两种含有2-（2-硝基苯基）丙氧羰基（NPPOC）保护的OH基的反应性亚磷酰胺单体制备的。逐步合成是在具有OH功能的可溶性聚苯乙烯载体上进行的，该载体允许通过在非溶剂中沉淀进行再循环。为了制备具有不同长度和序列的低聚物，进行了包括亚磷酰胺偶联，亚磷酸盐氧化成磷酸盐以及通过在λ= 365 nm处的光照射进行的NPPOC脱保护的重复循环。合成以微摩尔规模进行，并且在所有情况下均获得良好的回收率。¹ H NMR，UV光谱和尺寸排阻色谱法，从而确定最佳合成条件。从支持物上裂解后，通过串联质谱对低聚（磷酸二酯）进行表征，这证实了均一序列编码低聚物的制备。

更新日期：2017-11-16

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