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Prebiotic Phosphate Ester Syntheses in a Deep Eutectic Solvent

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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.

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Acknowledgments

This work was jointly supported by NSF and the NASA Astrobiology Program, under the NSF Center for Chemical Evolution, CHE-1004570 (MG, MZ, FF), and by the NASA Exobiology and Evolutionary Biology Program, NNX10AT30G (MAP). We thank Edwin Rivera from the USF NMR facility for research assistance. The authors thank Nicholas V. Hud, Ram Krishnamurthy, and Terry Kee for useful discussions. Maheen Gull also thanks Virginia Pasek and Danny Lindsay for their support and to her mother and sisters for their love and patience as well as her beloved father who passed away while the research work of this manuscript was going on.

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Authors and Affiliations

  1. School of Geosciences, University of South Florida, NES 107, 4202 East Fowler Ave, Tampa, FL, 33620, USA

    Maheen Gull & Matthew A. Pasek

  2. School of Chemistry and Biochemistry, Georgia Institute of Technology, 901 Atlantic Drive, Atlanta, GA, 30332, USA

    Manshui Zhou & Facundo M. Fernández

Authors
  1. Maheen Gull
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  2. Manshui Zhou
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  3. Facundo M. Fernández
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  4. Matthew A. Pasek
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Correspondence to Matthew A. Pasek.

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Gull, M., Zhou, M., Fernández, F.M. et al. Prebiotic Phosphate Ester Syntheses in a Deep Eutectic Solvent. J Mol Evol 78, 109–117 (2014). https://doi.org/10.1007/s00239-013-9605-9

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  • DOI: https://doi.org/10.1007/s00239-013-9605-9

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