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Cyanamide as a prebiotic phosphate activating agent – catalysis by simple 2-oxoacid salts

Cyanamide is a prebiotically plausible compound that has previously been invoked as a phosphate activating agent. However, its reactions with phosphate monoesters are very slow and tend to be low yielding. We now report a fast and efficient phosphate activation reaction using cyanamide in the presen...

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Detalles Bibliográficos
Autores principales: Tsanakopoulou, Maria, Sutherland, John D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5708344/
https://www.ncbi.nlm.nih.gov/pubmed/29043309
http://dx.doi.org/10.1039/c7cc07517k
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author Tsanakopoulou, Maria
Sutherland, John D.
author_facet Tsanakopoulou, Maria
Sutherland, John D.
author_sort Tsanakopoulou, Maria
collection PubMed
description Cyanamide is a prebiotically plausible compound that has previously been invoked as a phosphate activating agent. However, its reactions with phosphate monoesters are very slow and tend to be low yielding. We now report a fast and efficient phosphate activation reaction using cyanamide in the presence of glyoxylate or pyruvate. These simple 2-oxoacid salts are shown to function as catalysts and in an optimised system, adenosine-3′-phosphate was converted to adenosine-2′,3′-cyclic phosphate in 95% yield.
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spelling pubmed-57083442018-01-05 Cyanamide as a prebiotic phosphate activating agent – catalysis by simple 2-oxoacid salts Tsanakopoulou, Maria Sutherland, John D. Chem Commun (Camb) Chemistry Cyanamide is a prebiotically plausible compound that has previously been invoked as a phosphate activating agent. However, its reactions with phosphate monoesters are very slow and tend to be low yielding. We now report a fast and efficient phosphate activation reaction using cyanamide in the presence of glyoxylate or pyruvate. These simple 2-oxoacid salts are shown to function as catalysts and in an optimised system, adenosine-3′-phosphate was converted to adenosine-2′,3′-cyclic phosphate in 95% yield. Royal Society of Chemistry 2017-11-11 2017-10-18 /pmc/articles/PMC5708344/ /pubmed/29043309 http://dx.doi.org/10.1039/c7cc07517k Text en This journal is © The Royal Society of Chemistry 2017 https://creativecommons.org/licenses/by/3.0/This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Tsanakopoulou, Maria
Sutherland, John D.
Cyanamide as a prebiotic phosphate activating agent – catalysis by simple 2-oxoacid salts
title Cyanamide as a prebiotic phosphate activating agent – catalysis by simple 2-oxoacid salts
title_full Cyanamide as a prebiotic phosphate activating agent – catalysis by simple 2-oxoacid salts
title_fullStr Cyanamide as a prebiotic phosphate activating agent – catalysis by simple 2-oxoacid salts
title_full_unstemmed Cyanamide as a prebiotic phosphate activating agent – catalysis by simple 2-oxoacid salts
title_short Cyanamide as a prebiotic phosphate activating agent – catalysis by simple 2-oxoacid salts
title_sort cyanamide as a prebiotic phosphate activating agent – catalysis by simple 2-oxoacid salts
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5708344/
https://www.ncbi.nlm.nih.gov/pubmed/29043309
http://dx.doi.org/10.1039/c7cc07517k
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