Prebiotic phosphate ester syntheses in a deep eutectic solvent

J Mol Evol. 2014 Feb;78(2):109-17. doi: 10.1007/s00239-013-9605-9. Epub 2013 Dec 25.

Abstract

We report a route to synthesize a wide range of organophosphates of biological significance in a deep eutectic solvent (2:1 urea and choline chloride), utilizing various orthophosphate sources. Heating an organic alcohol in the solvent along with a soluble phosphorus source yields phosphorus esters of choline as well as that of the added organic in yields between 15 to 99 %. In addition, phosphite analogs of biological phosphates and peptides were also formed by the simple mixing of reagents and heating at 60-70 °C in the deep eutectic solvent. The presented dehydration reactions are relevant to prebiotic and green chemistry in alternative solvents.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Choline / chemistry
  • Esters
  • Organophosphates / chemical synthesis*
  • Prebiotics*
  • Solvents / chemistry*
  • Urea / chemistry

Substances

  • Esters
  • Organophosphates
  • Prebiotics
  • Solvents
  • Urea
  • Choline