1.14.16.5: alkylglycerol monooxygenase
This is an abbreviated version!
For detailed information about alkylglycerol monooxygenase, go to the full flat file.
Word Map on EC 1.14.16.5
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1.14.16.5
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alkylglycerols
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tetrahydrobiopterin
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hydroxylases
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bh4
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tetrahydrobiopterin-dependent
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biopterin
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pterins
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tetrahydropterins
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dihydropteridine
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phenylketonuria
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sepiapterin
- 1.14.16.5
- alkylglycerols
- tetrahydrobiopterin
- hydroxylases
- bh4
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tetrahydrobiopterin-dependent
- biopterin
- pterins
- tetrahydropterins
- dihydropteridine
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phenylketonuria
- sepiapterin
Reaction
Synonyms
AGMO, alkylglycerol mono-oxygenase, alkylglycerol monooxygenase, EC 1.14.99.17, glyceryl ether hydroxylase, glyceryl ether monooxygenase, glyceryl ether oxidase, glyceryl ether oxygenase, glyceryl ether-cleaving enzyme, glyceryl etherase, glyceryl-ether cleaving enzyme, O-alkylglycerol monooxygenase, oxygenase, glyceryl ether mono-, PRUB680
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Reaction
Reaction on EC 1.14.16.5 - alkylglycerol monooxygenase
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1-O-alkyl-sn-glycerol + a 5,6,7,8-tetrahydropteridine + O2 = 1-O-(1-hydroxyalkyl)-sn-glycerol + a 4a-hydroxy-5,6,7,8-tetrahydropteridine
1-O-alkyl-sn-glycerol + a 5,6,7,8-tetrahydropteridine + O2 = 1-O-(1-hydroxyalkyl)-sn-glycerol + a 4a-hydroxy-5,6,7,8-tetrahydropteridine
mechanism
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1-O-alkyl-sn-glycerol + a 5,6,7,8-tetrahydropteridine + O2 = 1-O-(1-hydroxyalkyl)-sn-glycerol + a 4a-hydroxy-5,6,7,8-tetrahydropteridine
The glyceryl ether substrate is first hydroxylated in a pteridine-dependent monooxygenase reaction to yield the unstable semiacetal product. The enzyme accepts a range of chain lengths from n = 11 to n = 20. The tetrahydrobiopterin cofactor is first converted to a 4alpha-hydroxy derivative and leaves the reaction after dehydration as 6,7[8H]-dihydrobiopterin, which is recycled to tetrahydrobiopterin by dihydropteridine reductase with NADH or NADPH. The semiacetal rearranges to the corresponding aldehyde and glycerol. In the presence of oxygen, the aldehyde is readily oxidized to the corresponding acid
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