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MetaCyc Enzyme: long-chain fatty acid ω-hydroxylase

Gene: CYP704B1 Accession Number: AT1G69500 (MetaCyc)

Species: Arabidopsis thaliana col

Summary:
The cDNA of CYP704B1 was expressed in yeast cells. The enzyme activity was demonstrated in an in vitro enzyme assay, where palmitate was transformed to 16-hydroxypalmitate. In addition to palmitate, CYP704B1 also acted on oleate, linoleate, α-linolenate and 9,10-epoxystearate. Laurate was a poor substrate. Phenolics such as cinnamate, p-coumarate, ferulate, sinapate and p-coumaroyl shikimate were not metabolized [Dobritsa09].

CYP704B1 had an anther-specific expression pattern and is highly coexpressed with CYP703A2, an in-chain fatty acid hydroxylase also involved in exine biosynthesis. CYP704B1 mutant plants have impaired pollen walls that lack a normal exine layer [Dobritsa09].

Unification Links: ArrayExpress:Q8GWJ5 , Pride:Q8GWJ5 , Protein Model Portal:Q9C788 , SMR:Q9C788 , String:3702.AT1G69500.1-P , UniProt:Q8GWJ5

Relationship Links: InterPro:IN-FAMILY:IPR001128 , InterPro:IN-FAMILY:IPR002401 , Pfam:IN-FAMILY:PF00067 , Prints:IN-FAMILY:PR00385 , Prints:IN-FAMILY:PR00463

Gene-Reaction Schematic: ?

Gene-Reaction Schematic

Instance reactions of [a long-chain fatty acid + NADPH + oxygen + H+ → an ω-hydroxy long-chain fatty acid + NADP+ + H2O] (1.14.13.cs):
i1: palmitate + NADPH + oxygen + H+ → 16-hydroxypalmitate + NADP+ + H2O (1.14.13.cs)

i2: (9R,10S)-dihydroxystearate + NADPH + oxygen + H+ → 9,10,18-trihydroxystearate + NADP+ + H2O (1.14.13.-)

i3: oleate + NADPH + oxygen + H+ → 18-hydroxyoleate + NADP+ + H2O (1.14.13.cs)

i4: 9,10-epoxystearate + NADPH + oxygen + H+ → 9,10-epoxy-18-hydroxystearate + NADP+ + H2O (1.14.13.-)

i5: stearate + NADPH + oxygen + H+ → 18-hydroxystearate + NADP+ + H2O (1.14.13.cs)

Credits:
Created 24-Feb-2011 by Zhang P , TAIR
Revised 18-Feb-2015 by Caspi R , SRI International


Enzymatic reaction of: oleate ω-hydroxylase (long-chain fatty acid ω-hydroxylase)

EC Number: 1.14.13.cs

oleate + NADPH + oxygen + H+ <=> 18-hydroxyoleate + NADP+ + H2O

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the Enzyme Commission system.

The reaction is favored in the direction shown.

In Pathways: sporopollenin precursors biosynthesis


Enzymatic reaction of: stearate ω-hydroxylase (long-chain fatty acid ω-hydroxylase)

EC Number: 1.14.13.cs

stearate + NADPH + oxygen + H+ <=> 18-hydroxystearate + NADP+ + H2O

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the Enzyme Commission system.

The reaction is favored in the direction shown.

In Pathways: sporopollenin precursors biosynthesis


Enzymatic reaction of: palmitate ω-hydroxylase (long-chain fatty acid ω-hydroxylase)

EC Number: 1.14.13.cs

palmitate + NADPH + oxygen + H+ <=> 16-hydroxypalmitate + NADP+ + H2O

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the Enzyme Commission system.

The reaction is favored in the direction shown.

In Pathways: sporopollenin precursors biosynthesis


Enzymatic reaction of: long-chain fatty acid ω-hydroxylase

EC Number: 1.14.13.cs

a long-chain fatty acid + NADPH + oxygen + H+ <=> an ω-hydroxy long-chain fatty acid + NADP+ + H2O

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the Enzyme Commission system.

The reaction is favored in the direction shown.

In Pathways: sporopollenin precursors biosynthesis


References

Dobritsa09: Dobritsa AA, Shrestha J, Morant M, Pinot F, Matsuno M, Swanson R, Moller BL, Preuss D (2009). "CYP704B1 is a long-chain fatty acid omega-hydroxylase essential for sporopollenin synthesis in pollen of Arabidopsis." Plant Physiol 151(2);574-89. PMID: 19700560


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.0 on Tue Aug 4, 2015, biocyc12.