| Cationic substrates of soybean lipoxygenase-1. | |
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MedLine Citation:
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PMID: 21257189 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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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. |
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Authors:
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Lucas E Chohany; Kathleen A Bishop; Hannah Camic; Stephen J Sup; Peter M Findeis; Charles H Clapp |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2010-12-30 |
Journal Detail:
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Title: Bioorganic chemistry Volume: - ISSN: 1090-2120 ISO Abbreviation: - Publication Date: 2010 Dec |
Date Detail:
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Created Date: 2011-1-24 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 1303703 Medline TA: Bioorg Chem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
Copyright Information:
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Copyright © 2011 Elsevier Inc. All rights reserved. |
Affiliation:
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Department of Chemistry, Bucknell University, Lewisburg, PA 17837, United States. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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