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具有前体生物学意义的化学反应中C-C、C-O、C=O和C-N键的形成与演化。

Formation and evolution of C-C, C-O, C[double bond, length as m-dash]O and C-N bonds in chemical reactions of prebiotic interest.

作者信息

Arias Alejandro, Gómez Sara, Rojas-Valencia Natalia, Núñez-Zarur Francisco, Cappelli Chiara, Murillo-López Juliana A, Restrepo Albeiro

机构信息

Instituto de Química, Universidad de Antioquia UdeA Calle 70 No. 52-21 Medellín Colombia

Scuola Normale Superiore, Classe di Scienze Piazza dei Cavalieri 7 Pisa 56126 Italy

出版信息

RSC Adv. 2022 Oct 10;12(44):28804-28817. doi: 10.1039/d2ra06000k. eCollection 2022 Oct 4.

DOI:10.1039/d2ra06000k
PMID:36320504
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9549586/
Abstract

A series of prebiotic chemical reactions yielding the precursor building blocks of amino acids, proteins and carbohydrates, starting solely from HCN and water is studied here. We closely follow the formation and evolution of the pivotal C-C, C-O, C[double bond, length as m-dash]O, and C-N bonds, which dictate the chemistry of the molecules of life. In many cases, formation of these bonds is set in motion by proton transfers in which individual water molecules act as catalysts so that water atoms end up in the products. Our results indicate that the prebiotic formation of carbon dioxide, formaldehyde, formic acid, formaldimine, glycolaldehyde, glycine, glycolonitrile, and oxazole derivatives, among others, are best described as highly nonsynchronous concerted single step processes. Nonetheless, for all reactions involving double proton transfer, the formation and breaking of O-H bonds around a particular O atom occur in a synchronous fashion, apparently independently from other primitive processes. For the most part, the first process to initiate seems to be the double proton transfer in the reactions where they are present, then bond breaking/formation around the reactive carbon in the carbonyl group and finally rupture of the C-N bonds in the appropriate cases, which are the most reluctant to break. Remarkably, within the limitations of our non-dynamical computational model, the wide ranges of temperature and pressure in which these reactions occur, downplay the problematic determination of the exact constraints on the early Earth.

摘要

本文研究了一系列仅从HCN和水开始的益生元化学反应,这些反应产生了氨基酸、蛋白质和碳水化合物的前体构建单元。我们密切关注关键的C-C、C-O、C=O和C-N键的形成和演化,这些键决定了生命分子的化学性质。在许多情况下,这些键的形成是由质子转移引发的,其中单个水分子充当催化剂,使得水原子最终出现在产物中。我们的结果表明,二氧化碳、甲醛、甲酸、甲亚胺、乙醇醛、甘氨酸、乙醇腈和恶唑衍生物等的益生元形成,最好被描述为高度非同步的协同单步过程。尽管如此,对于所有涉及双质子转移的反应,特定O原子周围O-H键的形成和断裂以同步方式发生,显然独立于其他原始过程。在大多数情况下,首先启动的过程似乎是存在双质子转移的反应中的双质子转移,然后是羰基中反应性碳周围的键断裂/形成,最后在适当情况下是最不易断裂的C-N键的断裂。值得注意的是,在我们的非动态计算模型的限制范围内,这些反应发生的广泛温度和压力范围,淡化了对早期地球确切限制的问题确定。

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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0de3/9549586/373f732491c4/d2ra06000k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0de3/9549586/1ae5e4a921b9/d2ra06000k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0de3/9549586/f7d97fd3d6ca/d2ra06000k-f1.jpg
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