Environmental Chemistry Letters

, Volume 3, Issue 2, pp 70–73 | Cite as

Dynamic behaviour of 1-aminopropan-2-one in sewage: a preliminary synthetic and spectroscopic study

  • M. F. Fitzsimons
  • S. T. Belt
Original paper


A preliminary investigation of the solution phase behaviour of the biomarker compound 1-aminopropan-2-one (APR) using NMR spectroscopy was carried out. This was achieved, in part, by synthesis of APR with13C-enrichment in the methylene position. In this paper, we report that this biomarker undergoes H/D exchange with D2O, probably via an enol intermediate. In addition, use of13C-enriched APR enabled its detection by13C NMR spectroscopy at environmentally relevant concentrations.


1-aminopropan-2-one NMR spectroscopy Isotope Ketone Enol Biomarker Synthesis 



We thank the Royal Society of Chemistry for a research grant and Andrew Tonkin (University of Plymouth) for the synthesis of 13C-APR.


  1. Atkinson D, Chechik V (2004) An NMR study of isotope effect on keto-enol tautomerization. J Chem Educ 81:1030–1033CrossRefGoogle Scholar
  2. Belt ST, Allard WG, Massé G, Robert J-M, Rowland SJ (2000) Highly branched isoprenoids (HBIs): identification of the most common and abundant sedimentary isomers. Geochim Cosmochim Acta 64:3839–3851CrossRefGoogle Scholar
  3. Dawit M, Williams ID, Fitzsimons MF (2001). Determination of 1-aminopropan-2-one, a dissolved sewage component, in water samples. Water Res 35:1151–1156CrossRefGoogle Scholar
  4. Deng Y, Yu PH (1999) Simultaneous determination of formaldehyde and methylglyoxal in urine: Involvement of semicarbazide-sensitive amine oxidase-mediated deamination in diabetic complications. J Chromatogr Sci 37:317–322PubMedGoogle Scholar
  5. Fitzsimons MF, Abdul-Rashid MK, Riley JP, Wolff GA (1995) Aminopropanone as a marker for raw sewage in natural waters. Mar Pollut Bull 30:306–312CrossRefGoogle Scholar
  6. Henrichs SM (1995) Sedimentary organic matter preservation: an assessment and speculative synthesis. Mar Chem 49:127–136CrossRefGoogle Scholar
  7. Hepworth JD (1965) Aminacetone semicarbazone hydrochloride (amino-2 propanone, semicarbazone hydrochloride). Org Synth 45:27–29Google Scholar
  8. Mathys KC, Ponnampalam SN, Padival S, Nagaraj RH (2002) Semicarbazide-sensitive amine oxidase in aortic smooth muscle cells mediates synthesis of a methylglyoxal-AGE: implications for vascular complications in diabetes. Biochem Biophys Res Commun 297:863–869CrossRefGoogle Scholar
  9. Turner JM (1967) L-1-aminopropan-2-ol dehydrogenase and l-threonine dehydrogenase in Escherichia coli. Biochem J 104:112–121PubMedGoogle Scholar
  10. Urata G, Granick S (1963) Biosynthesis of α-aminoketones and the metabolism of aminoacetone. J Biol Chem 238:811–820PubMedGoogle Scholar
  11. Williams DH, Fleming I (1995) Spectroscopic methods in organic chemistry, 5th edn. McGraw-Hill, LondonGoogle Scholar

Copyright information

© Springer-Verlag 2005

Authors and Affiliations

  1. 1.Petroleum and Environmental Geochemistry Group, School of Earth, Ocean and Environmental SciencesUniversity of PlymouthPlymouthUK

Personalised recommendations