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Issue 42, 2017
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Hydroxyapatite: catalyst for a one-pot pentose formation

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Abstract

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 1H-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.

Graphical abstract: Hydroxyapatite: catalyst for a one-pot pentose formation

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Publication details

The article was received on 17 Aug 2017, accepted on 20 Sep 2017 and first published on 27 Sep 2017


Article type: Paper
DOI: 10.1039/C7OB02051A
Citation: Org. Biomol. Chem., 2017,15, 8888-8893
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    Hydroxyapatite: catalyst for a one-pot pentose formation

    K. Usami and A. Okamoto, Org. Biomol. Chem., 2017, 15, 8888
    DOI: 10.1039/C7OB02051A

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