Alkylglycerol monooxygenase

alkylglycerol monooxygenase
Identifiers
EC number	1.14.16.5
CAS number	37256-82-9
Databases
IntEnz	IntEnz view
BRENDA	BRENDA entry
ExPASy	NiceZyme view
KEGG	KEGG entry
MetaCyc	metabolic pathway
PRIAM	profile
PDB structures	RCSB PDB PDBe PDBsum
Gene Ontology	AmiGO / EGO
Search PMC articles PubMed articles NCBI proteins

Alkylglycerol monooxygenase (AGMO, ) (EC 1.14.16.5) is an enzyme that catalyzes the hydroxylation of alkylglycerols, a specific subclass of ether lipids. This enzyme was first described in 1964 as a pteridine-dependent etherlipid cleaving enzyme.^[1] In 2010 finally, the gene coding for alkylglycerol monooxygenase was discovered as transmembrane protein 195 (TMEM195) on chromosome 7.^[2] In analogy to the enzymes phenylalanine hydroxylase, tyrosine hydroxylase, tryptophan hydroxylase and nitric oxide synthase, alkylglycerol monooxygenase critically depends on the cofactor tetrahydrobiopterin and iron.

The reaction catalyzed by alkylglycerol monooxygenase:

• 1-alkyl-sn-glycerol + tetrahydrobiopterin + O₂ $\rightleftharpoons$ 1-hydroxyalkyl-sn-glycerol + 6,7[8H]-dihydrobiopterin + H₂O

The unstable intermediate product 1-hydroxyalkyl-sn-glycerol rearranges into the fatty aldehyde and the free glycerol derivative. The fatty aldehyde is then further oxidized to the corresponding acid by fatty aldehyde dehydrogenase.

Alkylglycerol monooxygenase is a membrane-bound mixed-function oxidase and harbours a fatty acid hydroxylase motif. The iron is believed to be coordinated by a diiron center composed of eight histidines, which can be found in all enzymes containing this motif.

Nomenclature

The systematic name for this enzyme is 1-alkyl-sn-glycerol,tetrahydrobiopterin:oxygen oxidoreductase. Other names in use are glyceryl-ether monooxygenase, glyceryl-ether cleaving enzyme, glyceryl ether oxygenase, glyceryl etherase, and O-alkylglycerol monooxygenase.

References

1. Tietz, AA; Lindberg, M; Kennedy, EP (December 1964). "A New Pteridine-Requiring Enzyme System For The Oxidation Of Glyceryl Ethers.". The Journal of Biological Chemistry 239: 4081–90. PMID 14247652.
2. Watschinger, K (2010). "Identification of the gene encoding alkylglycerol monooxygenase defines a third class of tetrahydrobiopterin-dependent enzymes". Proc. Natl. Acad. Sci. U.S.A 107 (31): 13672–13677. doi:10.1073/pnas.1002404107. PMC 2922233. PMID 20643956.

Further reading

• Watschinger K, Keller MA, Hermetter A, Golderer G, Werner-Felmayer G, Werner ER (2009). "Glyceryl ether monooxygenase resembles aromatic amino acid hydroxylases in metal ion and tetrahydrobiopterin dependence". Biol. Chem. 390: 3–10. doi:10.1515/BC.2009.010. PMC 2847825. PMID 19007315.
• Werner ER, Hermetter A, Prast H, Golderer G, Werner-Felmayer G (2007). "Widespread occurrence of glyceryl ether monooxygenase activity in rat tissues detected by a novel assay". J. Lipid Res. 48 (6): 1422–1427. doi:10.1194/jlr.D600042-JLR200. PMC 2851153. PMID 17303893.
• Ishibashi T, Imai Y (1983). "Solubilization and partial characterization of alkylglycerol monooxygenase from rat liver microsomes". Eur. J. Biochem. 132 (1): 23–7. doi:10.1111/j.1432-1033.1983.tb07320.x. PMID 6840084.
• Pfleger RC, Piantadosi C, Snyder F (1967). "The biocleavage of isomeric glyceryl ethers by soluble liver enzymes in a variety of species". Biochim. Biophys. Acta 144 (3): 633–48. doi:10.1016/0005-2760(67)90052-5. PMID 4383918.
• Snyder F, Malone B, Piantadosi C (1973). "Tetrahydropteridine-dependent cleavage enzyme for O-alkyl lipids: substrate specificity". Biochim. Biophys. Acta 316 (2): 259–65. doi:10.1016/0005-2760(73)90018-0. PMID 4355017.
• Soodsma JF, Piantadosi C, Snyder F (1972). "Partial characterization of the alkylglycerol cleavage enzyme system of rat liver". J. Biol. Chem. 247 (12): 3923–9. PMID 4402391.