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Title of article :
Cationic substrates of soybean lipoxygenase-1
Author/Authors :
Chohany، نويسنده , , Lucas E. and Bishop، نويسنده , , Kathleen A. and Camic، نويسنده , , Hannah and Sup، نويسنده , , Stephen J. and Findeis، نويسنده , , Peter M. and Clapp، نويسنده , , Charles H.، نويسنده ,
Issue Information :
روزنامه با شماره پیاپی سال 2011
Pages :
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Abstract :
Soybean lipoxygenase-1 (SBLO-1) catalyzes the oxygenation of 1,4-dienes to produce conjugated diene hydroperoxides. The best substrates are anions of fatty acids; for example, linoleate is converted to 13(S)-hydroperoxy-9(Z),11(E)-octadecadienoate. The manner in which SBLO-1 binds substrates is uncertain. In the present work, it was found that SBLO-1 will oxygenate linoleyltrimethylammonium ion (LTMA) to give primarily13(S)-hydroperoxy-9(Z),11(E)-octadecadienyltrimethylammonium ion. The rate of this process is about the same at pH 7 and pH 9 and is about 30% of the rate observed with linoleate at pH 9. At pH 7, SBLO-1 oxygenates linoleyldimethylamine (LDMA) to give primarily 13(S)-hydroperoxy-9(Z),11(E)-octadecadienyldimethylamine. The oxygenation of LDMA occurs at about the same rate as LTMA at pH 7, but more slowly at pH 9. The results demonstrate that SBLO-1 will readily oxygenate substrates in which the carboxylate of linoleate is replaced with a cationic group, and the products of these reactions have the same stereo- and regiochemistry as the products obtained from fatty acid substrates.
Keywords :
substrate binding , Stereochemistry , Linoleyldimethylamine , Linoleyltrimethylammonium ion , lipoxygenase , Specificity
Journal title :
Bioorganic Chemistry: an International Journal
Journal title :
Bioorganic Chemistry: an International Journal
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