Prebiotic Synthesis of Glycolaldehyde and Glyceraldehyde from Formaldehyde: A Computational Study on the Initial Steps of the Formose Reaction

Author:

Venturini Alessandro1ORCID,González Javier2ORCID

Affiliation:

1. Institute of Organic Synthesis and Photoreactivity (ISOF) National Research Council of Italy Via P. Gobetti 101 40129 -Bologna Italy

2. Departamento de Química Orgánica e Inorgánica Universidad de Oviedo c/ Julián Clavería 8 33006- Oviedo Spain

Abstract

AbstractIn this work, the initial steps of the mechanism of the Formose reaction (FR) is computationally studied using DFT methods. The FR has been considered to be a relevant process in the prebiotic evolution leading to several types of sugars or carbohydrates. These molecules are some of the basic building blocks of the life. The dimerization of formaldehyde was found to take place via an intramolecular deprotonation reaction, leading to the formation of an intermediate which, after an isomerization, forms a Ca‐complex of the cis‐enediol tautomer of glycolaldehyde. The aldol reaction of this complex with additional formaldehyde gave glyceraldehyde, the simplest aldotriose. The catalyst Ca(OH)2 plays a dual role in the reaction, acting as a base (in the intramolecular deprotonation) and as Lewis acid (activating the carbonyl group) in the aldol addition.

Publisher

Wiley

Subject

General Chemistry

Reference41 articles.

1. Historical Development of Origins Research

2. Introduction: Chemical Evolution and the Origins of Life

3. Prebiotic Systems Chemistry: New Perspectives for the Origins of Life

4. TheHadean Eon(International Commision on Stratigraphy www.stratigraphy.org) is the period betwen −4600 and −4000 millions of years.

5. The molecules essential for life seems to have originated in a very early period of the history of the Earth (usually calledPrebiotic Evolution). Even though that the hypothesis and proposals about this process have changed it seems appropriate to mention the pioneer experiments by Miller:

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