Abstract
Stereospecificity of oxygen addition distinguishes lipoxygenase initiated lipid peroxidation from nonenzymatic autoxidation that produces a racemic mixture. Similarly, the positional and stereoconfiguration of lipoxygenase metabolites of un saturated fatty acids determine their precise physiological bioactivity. Teleost fish gills produce predominantly the 12 hydroxy derivative of arachidonic and eicosapentaenoic acids. Following reaction of arachidonic acid with fish gill lipoxygenase, 12‐hydroxyeicosatetraenoic acid (12‐HETE) was isolated using column chromatography and HPLC. Chiral phase HPLC revealed that the single 12(S) HETE isomer was produced by the enzyme. Proton NMR further confirmed the structure as identical to the 12(S) HETE produced in mammalian platelets and lungs.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 437-448 |
| Number of pages | 12 |
| Journal | Journal of Food Biochemistry |
| Volume | 15 |
| Issue number | 6 |
| DOIs | |
| State | Published - 1991 |
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ASJC Scopus subject areas
- Food Science
- Biophysics
- Pharmacology
- Cell Biology
Cite this
STEREOCHEMICAL SPECIFICITY OF THE N‐9 LIPOXYGENASE OF FISH GILL. / WINKLER, M.; PILHOFER, G.; GERMAN, J. B.
In: Journal of Food Biochemistry, Vol. 15, No. 6, 1991, p. 437-448.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - STEREOCHEMICAL SPECIFICITY OF THE N‐9 LIPOXYGENASE OF FISH GILL
AU - WINKLER, M.
AU - PILHOFER, G.
AU - GERMAN, J. B.
PY - 1991
Y1 - 1991
N2 - Stereospecificity of oxygen addition distinguishes lipoxygenase initiated lipid peroxidation from nonenzymatic autoxidation that produces a racemic mixture. Similarly, the positional and stereoconfiguration of lipoxygenase metabolites of un saturated fatty acids determine their precise physiological bioactivity. Teleost fish gills produce predominantly the 12 hydroxy derivative of arachidonic and eicosapentaenoic acids. Following reaction of arachidonic acid with fish gill lipoxygenase, 12‐hydroxyeicosatetraenoic acid (12‐HETE) was isolated using column chromatography and HPLC. Chiral phase HPLC revealed that the single 12(S) HETE isomer was produced by the enzyme. Proton NMR further confirmed the structure as identical to the 12(S) HETE produced in mammalian platelets and lungs.
AB - Stereospecificity of oxygen addition distinguishes lipoxygenase initiated lipid peroxidation from nonenzymatic autoxidation that produces a racemic mixture. Similarly, the positional and stereoconfiguration of lipoxygenase metabolites of un saturated fatty acids determine their precise physiological bioactivity. Teleost fish gills produce predominantly the 12 hydroxy derivative of arachidonic and eicosapentaenoic acids. Following reaction of arachidonic acid with fish gill lipoxygenase, 12‐hydroxyeicosatetraenoic acid (12‐HETE) was isolated using column chromatography and HPLC. Chiral phase HPLC revealed that the single 12(S) HETE isomer was produced by the enzyme. Proton NMR further confirmed the structure as identical to the 12(S) HETE produced in mammalian platelets and lungs.
UR - http://www.scopus.com/inward/record.url?scp=84986513641&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84986513641&partnerID=8YFLogxK
U2 - 10.1111/j.1745-4514.1991.tb00427.x
DO - 10.1111/j.1745-4514.1991.tb00427.x
M3 - Article
AN - SCOPUS:84986513641
VL - 15
SP - 437
EP - 448
JO - Journal of Food Biochemistry
JF - Journal of Food Biochemistry
SN - 0145-8884
IS - 6
ER -