Glycosylation of a model proto-RNA nucleobase with non-ribose sugars: implications for the prebiotic synthesis of nucleosides†,Organic & Biomolecular Chemistry

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Glycosylation of a model proto-RNA nucleobase with non-ribose sugars: implications for the prebiotic synthesis of nucleosides†
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2017-12-20 00:00:00 , DOI: 10.1039/c7ob03017g
David M. Fialho _{1,

2,

3,

4,

5} , Kimberly C. Clarke _{1,

2,

3,

4,

5} , Megan K. Moore _{1,

2,

3,

4,

5} , Gary B. Schuster _{1,

2,

3,

4,

5} , Ramanarayanan Krishnamurthy _{3,

4,

5,

6,

7} , Nicholas V. Hud _{1,

2,

3,

4,

5}

Affiliation

The emergence of nucleosides is an important, but poorly understood, element of the origins of life. We show that 2,4,6-triaminopyrimidine (TAP), a possible ancestral nucleobase of RNA, is glycosylated in water by non-ribose sugars in yields comparable to those previously reported for its reaction with ribose. The various sugars surveyed include ketoses and aldoses; tetroses, pentoses, and hexoses and are neutral, anionic, or cationic. Though they vary greatly in structure and properties, the data show that all sugars tested form glycosides with TAP. The structures of the eight TAP glycosides formed with glucose and two of its derivatives, glucose-6-phosphate and N-acetylglucosamine, were found to be β-pyranosides with the glycosylation site on TAP varying with sugar identity. Our results suggest that prebiotic nucleoside formation would not have been restricted to ribose if ancestral RNA (or proto-RNA) utilized TAP and/or other proto-nucleobases with similar reactivities, and that the ability to form higher-order structures may have influenced proto-RNA monomer selection.

中文翻译：

使用非核糖糖的模型原始RNA核苷的糖基化：对核苷的益生元合成的意义†

核苷的出现是生命起源的重要但鲜为人知的元素。我们显示2,4,6-三氨基嘧啶（TAP），一种可能的祖先RNA核苷，在水中被非核糖糖基糖基化，其产量与先前报道的与核糖反应的可比性相当。调查的各种糖包括酮糖和醛糖；四糖，戊糖和己糖，是中性，阴离子或阳离子的。尽管它们的结构和性质差异很大，但数据显示所有测试的糖都与TAP形成糖苷。八个TAP糖苷的结构由葡萄糖及其两个衍生物（6-磷酸葡萄糖和N发现-乙酰基葡糖胺是β-吡喃糖苷，其TAP上的糖基化位点随糖的同一性而变化。我们的结果表明，如果祖先RNA（或原RNA）利用TAP和/或其他具有类似反应性的原核碱基，则益生元核苷的形成将不会仅限于核糖，并且形成高级结构的能力可能会影响原核糖原。 -RNA单体选择。

更新日期：2017-12-20

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