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Specificity of oxidation of linoleic acid homologs by plant lipoxygenases

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Abstract

The lipoxygenase-catalyzed oxidation of linoleic acid homologs was studied. While the linoleic acid oxidation by maize 9-lipoxygenase (9-LO) specifically produced (9S)-hydroperoxide, the dioxygenation of (11Z,14Z)-eicosadienoic (20:2) and (13Z,16Z)-docosadienoic (22:2) acids by the same enzyme lacked regio- and stereospecificity. The oxidation of 20:2 and 22:2 by 9-LO afforded low yields of racemic 11-, 12-, 14-, and 15-hydroperoxides or 13- and 17-hydroperoxides, respectively. Soybean 13-lipoxygenase-1 (13-LO) specifically oxidized 20:2, 22:2, and linoleate into (ω6S)-hydroperoxides. Dioxygenation of (9Z,12Z)-hexadecadienoic acid (16:2) by both 9-LO and 13-LO occurred specifically, affording (9S)- and (13S)-hydroperoxides, respectively. The data are consistent with the “pocket theory of lipoxygenase catalysis” (i.e. with the penetration of a substrate into the active center with the methyl end first). Our findings also demonstrate that the distance between carboxyl group and double bonds substantially determines the positioning of substrates within the active site.

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Abbreviations

GC-MS:

gas chromatography-mass spectrometry

HPLC:

high performance liquid chromatography

9-LO:

maize 9-lipoxygenase CSSAP 92

13-LO:

soybean lipoxygenase-1

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Authors and Affiliations

  1. Kazan Institute of Biochemistry and Biophysics, Kazan Scientific Center, Russian Academy of Sciences, ul. Lobachevskogo 2/31, 420111, Kazan, Russia

    I. R. Chechetkin, E. V. Osipova, N. B. Tarasova, F. K. Mukhitova, Y. V. Gogolev & A. N. Grechkin

  2. Department of Medical Biochemistry and Biophysics, Division of Physiological Chemistry II, Karolinska Institutet, SE-171 77, Stockholm, Sweden

    M. Hamberg

Authors
  1. I. R. Chechetkin
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  2. E. V. Osipova
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  3. N. B. Tarasova
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  4. F. K. Mukhitova
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  5. M. Hamberg
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  6. Y. V. Gogolev
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  7. A. N. Grechkin
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Correspondence to I. R. Chechetkin.

Additional information

Original Russian Text © I. R. Chechetkin, E. V. Osipova, N. B. Tarasova, F. K. Mukhitova, M. Hamberg, Y. V. Gogolev, A. N. Grechkin, 2009, published in Biokhimiya, 2009, Vol. 74, No. 8, pp. 1052–1059.

Originally published in Biochemistry (Moscow) On-Line Papers in Press, as Manuscript BM09-020, June 21, 2009.

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Chechetkin, I.R., Osipova, E.V., Tarasova, N.B. et al. Specificity of oxidation of linoleic acid homologs by plant lipoxygenases. Biochemistry Moscow 74, 855–861 (2009). https://doi.org/10.1134/S0006297909080069

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  • DOI: https://doi.org/10.1134/S0006297909080069

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