UCL Discovery
UCL home » Library Services » Electronic resources » UCL Discovery

Prebiotic selection and assembly of proteinogenic amino acids and natural nucleotides from complex mixtures

Islam, S; Bucar, DK; Powner, MW; (2017) Prebiotic selection and assembly of proteinogenic amino acids and natural nucleotides from complex mixtures. Nature Chemistry , 9 pp. 584-589. 10.1038/nchem.2703. Green open access

[thumbnail of Accepted Manuscript for Prebiotic selection and assembly of proteinogenic amino acids and natural nucleotides from complex mixtures pdf.pdf]
Preview
Text
Accepted Manuscript for Prebiotic selection and assembly of proteinogenic amino acids and natural nucleotides from complex mixtures pdf.pdf - Accepted Version

Download (2MB) | Preview

Abstract

A central problem for the prebiotic synthesis of biological amino acids and nucleotides is to avoid the concomitant synthesis of undesired or irrelevant by-products. Additionally, multistep pathways require mechanisms that enable the sequential addition of reactants and purification of intermediates that are consistent with reasonable geochemical scenarios. Here, we show that 2-aminothiazole reacts selectively with two- and three-carbon sugars (glycolaldehyde and glyceraldehyde, respectively), which results in their accumulation and purification as stable crystalline aminals. This permits ribonucleotide synthesis, even from complex sugar mixtures. Remarkably, aminal formation also overcomes the thermodynamically favoured isomerization of glyceraldehyde into dihydroxyacetone because only the aminal of glyceraldehyde separates from the equilibrating mixture. Finally, we show that aminal formation provides a novel pathway to amino acids that avoids the synthesis of the non-proteinogenic α,α-disubstituted analogues. The common physicochemical mechanism that controls the proteinogenic amino acid and ribonucleotide assembly from prebiotic mixtures suggests that these essential classes of metabolite had a unified chemical origin.

Type: Article
Title: Prebiotic selection and assembly of proteinogenic amino acids and natural nucleotides from complex mixtures
Open access status: An open access version is available from UCL Discovery
DOI: 10.1038/nchem.2703
Publisher version: http://doi.org/10.1038/nchem.2703
Language: English
Additional information: This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions.
Keywords: Organic chemistry, chemical origin of life
UCL classification: UCL
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/1535381
Downloads since deposit
457Downloads
Download activity - last month
Download activity - last 12 months
Downloads by country - last 12 months

Archive Staff Only

View Item View Item