NADPH-DEPENDENT BETA-OXIDATION OF UNSATURATED FATTY-ACIDS WITH DOUBLE-BONDS EXTENDING FROM ODD-NUMBERED CARBON-ATOMS

被引:83
作者
SMELAND, TE [1 ]
NADA, M [1 ]
CUEBAS, D [1 ]
SCHULZ, H [1 ]
机构
[1] MANHATTAN COLL COLL MT ST VINCENT,JOINED DEPT CHEM,RIVERDALE,NY 10471
关键词
5-ENOYL-COA; DELTA-3; DELTA-2-ENOYL-COA ISOMERASE; DELTA-3,5,DELTA-2,4-DIENOYL-COA ISOMERASE; 2,4-DIENOYL-COA REDUCTASE;
D O I
10.1073/pnas.89.15.6673
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
The mitochondrial metabolism of 5-enoyl-CoAs, which are formed during the beta-oxidation of unsaturated fatty acids with double bonds extending from odd-numbered carbon atoms, was studied with mitochondrial extracts and purified enzymes of beta-oxidation. Metabolites were identified spectrophotometrically and by high performance liquid chromatography. 5-cis-Octenoyl-CoA, a putative metabolite of linolenic acid, was efficiently dehydrogenated by medium-chain acyl-CoA dehydrogenase (EC 1.3.99.3) to 2-trans-5-cis-octadienoyl-CoA, which was isomerized to 3,5-octadienoyl-CoA either by mitochondrial DELTA-3,DELTA-2-enoyl-CoA isomerase (EC 5.3.3.8) or by peroxisomal trifunctional enzyme. Further isomerization of 3,5-octadienoyl-CoA to 2-trans-4-trans-octadienoyl-CoA in the presence of soluble extracts of either rat liver or rat heart mitochondria was observed and attributed to a DELTA-3,5,DELTA-2,4-dienoyl-CoA isomerase. Qualitatively similar results were obtained with 2-trans-5-trans-octadienoyl-CoA formed by dehydrogenation of 5-trans-octenoyl-CoA. 2-trans-4-trans-Octadienoyl-CoA was a substrate for NADPH-dependent 2,4-dienoyl-CoA reductase (EC 1.3.1.34). A soluble extract of rat liver mitochondria catalyzed the isomerization of 2-trans-5-cis-octadienoyl-CoA to 2-trans-4-trans-octadienoyl-CoA, which upon addition of NADPH, NAD+, and CoA was chain-shortened to hexanoyl-CoA, butyryl-CoA, and acetyl-CoA. Thus we conclude that odd-numbered double bonds, like even-numbered double bonds, can be reductively removed during the beta-oxidation of polyunsaturated fatty acids.
引用
收藏
页码:6673 / 6677
页数:5
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