Recognition-encoded melamine oligomers (REMO) are synthetic polymers with an alternating 1,3,5-triazine-piperazine backbone and side chains equipped with either a phenol or phosphine oxide recognition unit. Here, we describe an automated method for highly efficient solid-phase synthesis (SPS) of REMO of any specified length and sequence. These SPS protocols are amongst the most robust reported to date, as demonstrated by the synthesis of a mixed-sequence 42-mer, which was obtained in excellent crude purity on a 100 mg scale. Starting from loaded Wang resin and dichlorotriazine monomer building blocks, the SPS methods were automated and optimised on a commercial peptide synthesiser. Major side products were identified using LCMS, and the undesired side reactions were suppressed by the choice of resin, solvent and coupling conditions. REMO have been shown to form high-fidelity length- and sequence-selective H-bonded duplexes, analogous to nucleic acids, and automated synthesis will facilitate exploration of related functional properties, such as molecular replication and programmable self-assembly.

中文翻译：

---

识别编码三聚氰胺低聚物的高效自动化固相合成

识别编码三聚氰胺低聚物 (REMO) 是一种合成聚合物，具有交替的 1,3,5-三嗪-哌嗪主链和配备有苯酚或氧化膦识别单元的侧链。在这里，我们描述了一种高效固相合成（SPS）任何指定长度和序列的 REMO 的自动化方法。这些 SPS 方案是迄今为止报道的最可靠的方案之一，混合序列 42 聚体的合成证明了这一点，该方案以 100 毫克规模获得了极佳的粗纯度。从加载的 Wang 树脂和二氯三嗪单体构建模块开始，SPS 方法在商用肽合成仪上进行自动化和优化。使用 LCMS 鉴定了主要副产物，并通过选择树脂、溶剂和偶联条件抑制了不需要的副反应。 REMO 已被证明可以形成高保真长度和序列选择性的氢键双链体，类似于核酸，自动合成将有助于探索相关的功能特性，例如分子复制和可编程自组装。