1.1.1.331: secoisolariciresinol dehydrogenase
This is an abbreviated version!
For detailed information about secoisolariciresinol dehydrogenase, go to the full flat file.
Word Map on EC 1.1.1.331
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1.1.1.331
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lignans
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podophyllotoxin
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forsythia
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podophyllum
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intermedia
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enterolactone
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plr
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hexandrum
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etoposide
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teniposide
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single-shot
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peltatum
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enantiospecific
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phase-shifting
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holography
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hologram
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pinoresinol-lariciresinol
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enterodiol
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koreana
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semi-synthetic
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pixel
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linum
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phytoestrogens
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+-pinoresinol
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versipellis
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cancer-preventative
- 1.1.1.331
-
lignans
- podophyllotoxin
- forsythia
- podophyllum
- intermedia
- enterolactone
- plr
- hexandrum
- etoposide
- teniposide
-
single-shot
- peltatum
-
enantiospecific
-
phase-shifting
-
holography
-
hologram
-
pinoresinol-lariciresinol
- enterodiol
- koreana
-
semi-synthetic
-
pixel
- linum
-
phytoestrogens
-
+-pinoresinol
- versipellis
-
cancer-preventative
Reaction
Synonyms
FkSIRD, matairesinol biosynthetic enzyme, PhSDH, PpSD, PpSDH, SDH, sdh-PpH, SDH_Pp7, secoisolariciresinol dehydrogenase, SirD, SSDH
ECTree
1.1.1.331 secoisolariciresinol dehydrogenaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 1.1.1.331 - secoisolariciresinol dehydrogenase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(-)-secoisolariciresinol + 2 NAD+
(-)-matairesinol + 2 NADH + 2 H+
-
-
product is optically pure, more than 99% enantiomeric excess. (-)-Matairesinol is formed preferentially in the in vitro reactions with enzyme preparations. The opposite (+)-enantiomer is isolated from Daphne genkwa shoot
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?
(-)-secoisolariciresinol + 2 NAD+
(-)-matairesinol + 2 NADH + 2 H+
-
-
product is optically pure, more than 99% enantiomeric excess. (-)-Matairesinol is formed preferentially in the in vitro reactions with enzyme preparations. The opposite (+)-enantiomer is isolated from Daphne odora callus
-
?
(-)-secoisolariciresinol + 2 NAD+
(-)-matairesinol + 2 NADH + 2 H+
-
-
-
?
(-)-secoisolariciresinol + 2 NAD+
(-)-matairesinol + 2 NADH + 2 H+
-
-
-
?
(-)-secoisolariciresinol + 2 NAD+
(-)-matairesinol + 2 NADH + 2 H+
the enantiomeric purity of formed (-)-matairesinol is over 99.9% in the reaction with the recombinant enzyme when tested with racemic secoisolariciresinol, high enantioselectivity, LC/MS and chiral HPLC analysis
-
-
?
(-)-secoisolariciresinol + 2 NAD+
(-)-matairesinol + 2 NADH + 2 H+
-
-
-
?
(-)-secoisolariciresinol + 2 NAD+
(-)-matairesinol + 2 NADH + 2 H+
-
-
-
-
?
(-)-secoisolariciresinol + 2 NAD+
(-)-matairesinol + 2 NADH + 2 H+
-
-
-
?
(-)-secoisolariciresinol + 2 NAD+
(-)-matairesinol + 2 NADH + 2 H+
conversion is enantiospecific, reaction proceeds via the corresponding lactol intermediate
-
-
?
(-)-secoisolariciresinol + 2 NAD+
(-)-matairesinol + 2 NADH + 2 H+
Phialocephala podophylli
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-
-
?
(-)-secoisolariciresinol + 2 NAD+
(-)-matairesinol + 2 NADH + 2 H+
Phialocephala podophylli PPE7
-
-
-
?
(-)-secoisolariciresinol + 2 NAD+
(-)-matairesinol + 2 NADH + 2 H+
-
-
-
?
(-)-secoisolariciresinol + 2 NAD+
(-)-matairesinol + 2 NADH + 2 H+
conversion is enantiospecific, reaction proceeds via the corresponding lactol intermediate
-
-
?
(-)-secoisolariciresinol + 2 NAD+
(-)-matairesinol + 2 NADH + 2 H+
NAD+ binds first followed by the substrate (-)-secoisolariciresinol. For hydride transfer, the incoming hydride abstracted from the substrate takes up the pro-S position in the NADH formed
-
-
?
(-)-secoisolariciresinol + 2 NAD+
(-)-matairesinol + 2 NADH + 2 H+
nicotinamide and the substrate are in the proper orientation for the well established B-face-specific hydride transfer to C-4 from the corresponding substrate reaction center, crystallization data. The Lys171 residue lowers the pKa of the phenolic hydroxyl group of the Tyr167 in the catalytic triad together with the positively charged NAD+. The Ser153 residue then shares its proton with the phenolic anionic group of Tyr167, and in this way, the latter can serve as a general base in substrate deprotonation during catalysis. Concomitant deprotonation of the (-)-secoisolariciresinol is then presumed to occur via the phenolic anion of Tyr167 with hydride transfer to NAD+, followed by nucleophilic attack to form the (-)-lactol intermediate from (-)-secoisolariciresinol. Subsequent dehydrogenation of the (-)-lactol can then occur by the same process involving Tyr167 as before and a newly bound NAD+ molecule to afford the dibenzyl furanone, (-)-matairesinol
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-
?
(-)-secoisolariciresinol + 2 NAD+
(-)-matairesinol + 2 NADH + 2 H+
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-
-
?
