Ashe, K;
Fernandez Garcia, C;
Coggins, A;
Corpinot, M;
Bucar, D-K;
Powner, M;
(2019)
Selective prebiotic synthesis ofphosphoroaminonitriles and aminothioamides inneutral water.
Nature Communications Chemistry
, 2
(23)
pp. 1-7.
10.1038/s42004-019-0124-5.
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Abstract
The central and conserved role of peptides in extant biology suggests that they played animportant role during the origins of life. Strecker amino acid synthesis appears to be prebiotic,but the high pKaHof ammonia (pKaH=9.2) necessitates high pH reaction conditions torealise efficient synthesis, which places difficult environmental constraints on prebiotic aminoacid synthesis. Here we demonstrate that diamidophosphate reacts efficiently with simplealdehydes and hydrogen cyanide in water at neutral pH to affordN-phosphoro-aminonitriles.N-Phosphoro-aminonitrile synthesis is highly selective for aldehydes; ketones give poorconversion.N-Phosphoro-aminonitriles react with hydrogen sulfide at neutral pH to furnishaminothioamides. The high yield (73%–Quant.) of N-phosphoro-aminonitriles at neutral pH, and their selective transformations, may provide new insights into prebiotic amino acid synthesis and activation.
| Type: | Article |
|---|---|
| Title: | Selective prebiotic synthesis ofphosphoroaminonitriles and aminothioamides inneutral water |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1038/s42004-019-0124-5 |
| Publisher version: | https://doi.org/10.1038/s42004-019-0124-5 |
| Language: | English |
| Additional information: | Open Access: This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/. |
| 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/10069104 |
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