TY - JOUR
T1 - Substrate stereochemistry of 2-methyl-branched-chain acyl-CoA dehydrogenase
T2 - elimination of one hydrogen each from pro-2S)-methyl and α-methine of isobutyryl-CoA
AU - Tanaka, Kay
AU - O'Shea, John J.
AU - Finocchiaro, Gaetano
AU - Ikeda, Yasuyuki
AU - Aberhart, D. John
AU - Ghoshal, Pallab K.
PY - 1986/9/26
Y1 - 1986/9/26
N2 - Dehydrogenation of (2S)-[3-13C]isobutyryl-CoA was carried out in vitro using 2-methyl-branched-chain acyl-CoA dehydrogenase purified from rat liver mitochondria. The product was subsequently hydrated by the addition of bovine crotonase. The resulting 3-hydroxyisobutyric acid was predominantly enriched with 13C at the β-hydroxy position as determined as a methyl ester using electron ionization-gas chromatography-mass spectroscopy. This finding indicates that isobutyryl-CoA is dehydrogenated stereospecifically at the (pro-2S)-methyl and α-methine groups to form methacrylyl-CoA, which is later hydrated with the addition of hydrogen on the same side of the molecule from which it was subtracted to produce 3-hydroxyisobutyryl-CoA.
AB - Dehydrogenation of (2S)-[3-13C]isobutyryl-CoA was carried out in vitro using 2-methyl-branched-chain acyl-CoA dehydrogenase purified from rat liver mitochondria. The product was subsequently hydrated by the addition of bovine crotonase. The resulting 3-hydroxyisobutyric acid was predominantly enriched with 13C at the β-hydroxy position as determined as a methyl ester using electron ionization-gas chromatography-mass spectroscopy. This finding indicates that isobutyryl-CoA is dehydrogenated stereospecifically at the (pro-2S)-methyl and α-methine groups to form methacrylyl-CoA, which is later hydrated with the addition of hydrogen on the same side of the molecule from which it was subtracted to produce 3-hydroxyisobutyryl-CoA.
KW - 2-methyl-branched-chain acyl-CoA
KW - Acyl-CoA dehydrogenase
KW - Substrate stereochemistry
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U2 - 10.1016/0167-4838(86)90059-2
DO - 10.1016/0167-4838(86)90059-2
M3 - Article
C2 - 3756180
AN - SCOPUS:0022551553
VL - 873
SP - 308
EP - 311
JO - Biochimica et Biophysica Acta - Protein Structure and Molecular Enzymology
JF - Biochimica et Biophysica Acta - Protein Structure and Molecular Enzymology
SN - 0167-4838
IS - 2
ER -