Studies on the biosynthesis of 2-hydroxy-1,4-benzoxazin-3-one (HBOA) from 3-hydroxyindolin-2-one in Zea mays.
The ring expansion of 3-hydroxyindolin-2-one to 2-hydroxy-1,4-benzoxazin-3-one (HBOA) was investigated by labelling experiments. Action of the cytochrome P450 enzyme BX4 from maize on 3-hydroxyindolin-2-one under an 18O2 atmosphere induced production of 2-hydroxy-1,4-benzoxazin-3-one in which the ring oxygen--but not the 2-hydroxy group of HBOA--is labelled. A mechanism for this transformation is proposed.
Spiteller
P
P
Department Chemie der Ludwig-Maximilians-Universität, Aachen, Germany.
Glawischnig
E
E
Gierl
A
A
Steglich
W
W
D048588:Benzoxazines; D001711:Biotransformation; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism*; D007211:Indoles / Q000378:metabolism*; D013058:Mass Spectrometry; D008968:Molecular Conformation; D015394:Molecular Structure; D010078:Oxazines / Q000378:metabolism*; D010103:Oxygen Isotopes; D003313:Zea mays / Q000378:metabolism*
C436752:2-hydroxy-1,4-benzoxazin-3-one; C436753:3-hydroxyindolin-2-one; D048588:Benzoxazines; D007211:Indoles; D010078:Oxazines; D010103:Oxygen Isotopes; D003577:Cytochrome P-450 Enzyme System