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Convenient syntheses of phosphinic analogues of γ-aminobutyric- and glutamic acids

Abstract

Three-steps, one-pot synthesis of 2-amino-4-(hydroxyphosphinyl)butyric acid from dibutyl ester of vinylphosphinic acid was carried out with an overall yield of 66%. 3-Aminopropylphosphinic acid was prepared from allylamine in three steps with an overall yield of 56%. These improved protocols allowed to obtain these commercially unavailable phosphinic analogues of glutamic acid and GABA for testing on potential molecular targets.

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Abbreviations

GABA:

4-aminobutyric acid

GABA-P H :

3-aminopropylphosphinic acid

Glu-γ-P H :

2-amino-4-(hydroxyphosphinyl) butyric acid

AIBN:

α,α',-azoisobutyronitrile

PT:

phosphinotricin, 2-amino-4-(hydroxymethylphosphinyl)butyric acid

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Correspondence to D. De Biase or A. R. Khomutov.

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Original Russian Text © M.A. Khomutov, A.A. Formanovsky, I.V. Mikhura, J. Vepsalainen, S.N. Kochetkov, D. De Biase, A.R. Khomutov, 2016, published in Bioorganicheskaya Khimiya, 2016, Vol. 42, No. 6, pp. 741–745.

The article was translated by the authors.

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Khomutov, M.A., Formanovsky, A.A., Mikhura, I.V. et al. Convenient syntheses of phosphinic analogues of γ-aminobutyric- and glutamic acids. Russ J Bioorg Chem 42, 672–676 (2016). https://doi.org/10.1134/S1068162016060042

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  • DOI: https://doi.org/10.1134/S1068162016060042

Keywords

  • amino acids
  • phosphorus analogues
  • glutamic acid
  • γ-aminobutyric acid (GABA)