Preparative singlet oxygenation of linoleate provides doubly allylic dihydroperoxides: putative intermediates in the generation of biologically active aldehydes in vivo.

Preparative singlet oxygenation of linoleate provides doubly allylic dihydroperoxides: putative intermediates in the generation of biologically active aldehydes in vivo. Research Abstract Details 

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Preparative singlet oxygenation of linoleate provides doubly allylic dihydroperoxides: putative intermediates in the generation of biologically active aldehydes in vivo. Abstract Text:

Wujuan Zhang,Mingjiang Sun,Robert G Salomon,

Photoinduced oxygenation generates biologically active, oxidatively truncated lipids in the retina. Previously, doubly allylic dihydroperoxides, 9,12-dihydroperoxyoctadeca-10,13-dienoic acid (9,12-diHPODE) and 10,13-dihydroperoxyoctadeca-8,11-dienoic acid (10,13-diHPODE), were postulated as key intermediates in the free radical-promoted oxidative fragmentation of linoleate that generates aldehydes, such as the cytotoxic gamma-hydroxyalkenal 4-hydroxy-2-nonenal (HNE), in vivo. We now report an efficient preparation of regioisomerically pure 9,12- and 10,13-diHPODE, devised to enable studies of their fragmentation reactions. Free radical-induced oxygenation of linoleate initially generates conjugated monohydroperoxy octadecadienoates (HPODEs) that are then converted into diHPODEs. In contrast, we found that singlet oxygenation of conjugated HPODEs does not produce diHPODEs. Unconjugated HPODEs are unique products of singlet oxygenation of linoleate that are coproduced with conjugated HPODEs. Preparative separation of the mixture of regioisomeric mono and diHPODEs generated by singlet oxygenation of linloeate is impractical. However, a simple tactic circumvented the problem. Thus, selective conversion of the undesired conjugated HPODEs into Diels-Alder adducts could be accomplished under mild conditions by reaction with N-phenyltriazolinedione. These adducts were readily removed, and the two remaining unconjugated HPODEs could then be easily isolated regioisomerically pure. Each of these was subsequently converted into a different, regioisomerically pure, diHPODE through further singlet oxygenation.

Preparative singlet oxygenation of linoleate provides doubly allylic dihydroperoxides: putative intermediates in the generation of biologically active aldehydes in vivo. Publishing Authors By Initials

W Zhang,M Sun,RG Salomon,

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Preparative singlet oxygenation of linoleate provides doubly allylic dihydroperoxides: putative intermediates in the generation of biologically active aldehydes in vivo. Journal Published:

PUBLICATION TYPE: Research Support, N.I.H., Extr

Journal: The Journal of organic chemistry

VOLUME: 71

Page Numbers: 5607-15

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ISSN: 0022-3263

DAY: 21

MONTH: Jul

YEAR: 2006

Preparative singlet oxygenation of linoleate provides doubly allylic dihydroperoxides: putative intermediates in the generation of biologically active aldehydes in vivo. Information

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LANGUAGE: eng

NlmUniqueID: 2985193

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Grant and Affiliation Information for Preparative singlet oxygenation of linoleate provides doubly allylic dihydroperoxides: putative intermediates in the generation of biologically active aldehydes in vivo.

AFFILIATION: Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106-7078, USA.

Country: United States

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MEDLINETA: J Org Chem

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