Usami K, Okamoto A
Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656, Japan.
Org Biomol Chem. 2017 Oct 31;15(42):8888-8893. doi: 10.1039/c7ob02051a.
One of the possible synthetic routes to pentoses is the formose reaction pathway from C1 and C2 carbon sources, but preferential ribose generation in a one-pot reaction without any control of conditions has not been reported. We have tested a one-pot pentose formation and analyzed the products and mechanism in the reaction, using H-NMR and mass spectrometry. Hydroxyapatite (HAp), which consists of phosphate and calcium ions, worked continuously for cross-aldol reactions and Lobry de Bruyn-van Ekenstein transformations to yield ribose from formaldehyde and glycolaldehyde. The continuous reaction proceeds in one pot in hot water only in the presence of a HAp catalyst, without any fine pH control or any complicated condition control at each reaction step. Ribose production by HAp may be a reason why a pentose backbone was incorporated into nucleic acids in the prebiotic world.
戊糖的一种可能合成途径是由C1和C2碳源通过甲醛聚糖反应途径，但在没有任何条件控制的一锅反应中优先生成核糖的情况尚未见报道。我们测试了一锅法形成戊糖，并使用氢核磁共振（H-NMR）和质谱分析了反应中的产物和机理。由磷酸根离子和钙离子组成的羟基磷灰石（HAp）持续催化交叉羟醛反应和洛布里·德·布吕恩-范·埃肯斯坦转化反应，从甲醛和乙醇醛生成核糖。该连续反应仅在热水中、有HAp催化剂存在的情况下于一个反应釜中进行，无需对每个反应步骤进行精确的pH控制或任何复杂的条件控制。HAp生成核糖可能是在生命起源之前的世界中戊糖主链被纳入核酸的一个原因。
