The Enzyme Database

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EC 1.14.19.74     
Accepted name: (+)-piperitol/(+)-sesamin synthase
Reaction: (1) (+)-pinoresinol + [reduced NADPH-hemoprotein reductase] + O2 = (+)-piperitol + [oxidized NADPH-hemoprotein reductase] + 2 H2O
(2) (+)-piperitol + [reduced NADPH-hemoprotein reductase] + O2 = (+)-sesamin + [oxidized NADPH-hemoprotein reductase] + 2 H2O
For diagram of sesamin biosynthesis, click here
Other name(s): CYP81Q1; CYP81Q2; PS; PSS; SS; piperitol synthase; sesamin synthase
Systematic name: (+)-pinoresinol,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (cyclizing)
Comments: A cytochrome P-450 (heme-thiolate) protein. Isolated from Sesamum indicum (sesame) and S. radiatum (black sesame).
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Ono, E., Nakai, M., Fukui, Y., Tomimori, N., Fukuchi-Mizutani, M., Saito, M., Satake, H., Tanaka, T., Katsuta, M., Umezawa, T. and Tanaka, Y. Formation of two methylenedioxy bridges by a Sesamum CYP81Q protein yielding a furofuran lignan, (+)-sesamin. Proc. Natl. Acad. Sci. USA 103 (2006) 10116–10121. [PMID: 16785429]
[EC 1.14.19.74 created 2018]
 
 
EC 2.1.5.1     
Accepted name: sesamin methylene transferase
Reaction: (1) (+)-sesamin + tetrahydrofolate = (+)-demethylpiperitol + 5,10-methylenetetrahydrofolate
(2) (+)-demethylpiperitol + tetrahydrofolate = (+)-didemethylpinoresinol + 5,10-methylenetetrahydrofolate
For diagram of sesamin catabolism, click here
Glossary: (+)-sesamin = 5,5′-[(1S,3aR,4S,6aR)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis(1,3-benzodioxole)
(+)-demethylpiperitol = 4-[(1S,3aR,4S,6aR)-4-(1,3-benzodioxol-5-yl)tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]benzene-1,2-diol
(+)-didemethylpinoresinol = 4-[(1S,3aR,4S,6aR)-4-(3,4-dihydroxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]benzene-1,2-diol
Other name(s): sesA (gene name)
Systematic name: (+)-sesamin:tetrahydrofolate N-methylenetransferase
Comments: This enzyme was characterized from the bacterium Sinomonas sp. No.22. It catalyses a cleavage of a methylene bridge, followed by the transfer of the methylene group to tetrahydrofolate. The enzyme is also active with (+)-episesamin, (–)-asarinin, (+)-sesaminol, (+)-sesamolin, and piperine.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Kumano, T., Fujiki, E., Hashimoto, Y. and Kobayashi, M. Discovery of a sesamin-metabolizing microorganism and a new enzyme. Proc. Natl. Acad. Sci. USA 113 (2016) 9087–9092. [DOI] [PMID: 27444012]
[EC 2.1.5.1 created 2018]
 
 


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