Selective prebiotic synthesis of phosphoroaminonitriles and aminothioamides in neutral water
Abstrak
The central and conserved role of peptides in extant biology suggests that they played an important role during the origins of life. Strecker amino acid synthesis appears to be prebiotic, but the high pKaH of ammonia (pKaH = 9.2) necessitates high pH reaction conditions to realise efficient synthesis, which places difficult environmental constraints on prebiotic amino acid synthesis. Here we demonstrate that diamidophosphate reacts efficiently with simple aldehydes and hydrogen cyanide in water at neutral pH to afford N-phosphoro-aminonitriles. N-Phosphoro-aminonitrile synthesis is highly selective for aldehydes; ketones give poor conversion. N-Phosphoro-aminonitriles react with hydrogen sulfide at neutral pH to furnish aminothioamides. 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.The Strecker reaction is thought to offer a prebiotically plausible synthesis of amino acids, but is reversible at the high or low pH ranges needed to promote reactivity. Here the reaction of hydrogen cyanide and diamidophosphate is shown to provide stable phosphorylated amino acid precursors at neutral pH, which can be hydrolysed to amino acids or thiolysed to thioamides.
Penulis (6)
Kathryn Ashe
C. Fernández-García
Merina K. Corpinot
Adam J. Coggins
Dejan-Krešimir Bučar
M. Powner
Akses Cepat
- Tahun Terbit
- 2019
- Bahasa
- en
- Total Sitasi
- 17×
- Sumber Database
- Semantic Scholar
- DOI
- 10.1038/s42004-019-0124-5
- Akses
- Open Access ✓