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陨石催化的分子间糖基化反应在质子束辐照下产生核苷。

Meteorite-catalyzed intermolecular -glycosylation produces nucleosides under proton beam irradiation.

作者信息

Bizzarri Bruno Mattia, Fanelli Angelica, Kapralov Michail, Krasavin Eugene, Saladino Raffaele

机构信息

Ecological and Biological Sciences Department (DEB), University of Tuscia Via S. Camillo de Lellis snc 01100 Viterbo Italy

Joint Institute for Nuclear Research, JINR's Laboratory of Radiation Biology Dubna Russia.

出版信息

RSC Adv. 2021 May 27;11(31):19258-19264. doi: 10.1039/d1ra02379a. eCollection 2021 May 24.

DOI:10.1039/d1ra02379a
PMID:35478633
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9033569/
Abstract

Di-glycosylated adenines act as glycosyl donors in the intermolecular -glycosylation of pyrimidine nucleobases under proton beam irradiation conditions. Formamide and chondrite meteorite NWA 1465 increased the yield and the selectivity of the reaction. The glycosyl transfer process was highly regioselective in yielding canonical -pyrimidine nucleosides, the natural β-anomers prevailing in the presence of formamide and NWA 1465. These data highlight the possible role of intermolecular -glycosylation in the prebiotic formation of purine and pyrimidine nucleosides, avoiding the occurrence of independent synthetic pathways.

摘要

双糖基化腺嘌呤在质子束辐照条件下作为嘧啶核碱基分子间糖基化反应中的糖基供体。甲酰胺和球粒陨石NWA 1465提高了反应的产率和选择性。糖基转移过程在生成标准β-嘧啶核苷方面具有高度区域选择性，在甲酰胺和NWA 1465存在下主要生成天然β-异头物。这些数据突出了分子间β-糖基化在嘌呤和嘧啶核苷的前生物形成中可能发挥的作用，避免了独立合成途径的出现。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/610a/9033569/b5ec5cb91b5b/d1ra02379a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/610a/9033569/22cfbc3d18e5/d1ra02379a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/610a/9033569/3a658da1a300/d1ra02379a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/610a/9033569/80fe2a93f102/d1ra02379a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/610a/9033569/12827bc96382/d1ra02379a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/610a/9033569/b5ec5cb91b5b/d1ra02379a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/610a/9033569/22cfbc3d18e5/d1ra02379a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/610a/9033569/3a658da1a300/d1ra02379a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/610a/9033569/80fe2a93f102/d1ra02379a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/610a/9033569/12827bc96382/d1ra02379a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/610a/9033569/b5ec5cb91b5b/d1ra02379a-s2.jpg

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Int J Mol Sci. 2021 Jan 18;22(2):917. doi: 10.3390/ijms22020917.
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Transition metal catalyzed glycosylation reactions - an overview.过渡金属催化的糖基化反应——概述。
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High-Energy Proton-Beam-Induced Polymerization/Oxygenation of Hydroxynaphthalenes on Meteorites and Nitrogen Transfer from Urea: Modeling Insoluble Organic Matter?
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Multicomponent Synthesis of Diaminopurine and Guanine PNA's Analogues Active against Influenza A Virus from Prebiotic Compounds.基于益生元化合物多组分合成对甲型流感病毒具有活性的二氨基嘌呤和鸟嘌呤肽核酸类似物
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