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Information on EC 1.2.1.44 - cinnamoyl-CoA reductase
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EC Tree
1.2.1.44 cinnamoyl-CoA reductaseIUBMB Comments
Acts also on a number of substituted cinnamoyl esters of coenzyme A.
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Word Map
- 1.2.1.44
- lignin
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cinnamyl
- monolignols
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phenylpropanoids
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lignification
- xylem
- caffeoyl-coa
- p-coumaroyl-coa
- leucocephala
- ccoaomt
- leucaena
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4-coumarate:coa
- gunnii
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sinapoyl
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guaiacyl
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syringyl
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cinnamyl-alcohol
- coniferaldehyde
- sinapoyl-coa
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lignin-specific
- sinapaldehyde
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non-condensed
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thioacidolysis
- biotechnology
- synthesis
- industry
- agriculture
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
cinnamoyl-coa reductase, cinnamoyl coa reductase, ll-ccrh1, bpccr1, cinnamoyl-coa reductase 1, ta-ccr2, sbccr1, atccr1, osccr1, sbccr2-2, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
CCR
CCR1
CCR2
CCRH1
cinnamoyl CoA reductase
cinnamoyl CoA reductase 1
cinnamoyl-CoA reductase
cinnamoyl-CoA reductase 1
cinnamoyl-CoA reductase1
cinnamoyl-CoA:NADPH reductase
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cinnamoyl-coenzyme A reductase
feruloyl coenzyme A reductase
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feruloyl-CoA reductase
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ferulyl-CoA reductase
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HcCCR1
p-hydroxycinnamoyl coenzyme A reductase
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reductase, cinnamoyl coenzyme A
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cinnamoyl-coenzyme A reductase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cinnamaldehyde + CoA + NADP+ = cinnamoyl-CoA + NADPH + H+
also acts on a number of substituted cinnamoyl esters of coenzyme A
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-
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cinnamaldehyde + CoA + NADP+ = cinnamoyl-CoA + NADPH + H+
although SbCCR1 displays higher affinity for caffeoyl-CoA or 4-coumaroyl-CoA than for feruloyl-CoA, the enzyme shows significantly higher activity for the latter substrate. In the first catalytic step, pro-R hydride transfer occurs from the C4 atom of NADPH to the reactive thioester carbonyl. The resulting oxyanion is temporarily stabilized by the oxyanion hole established from the side chain hydroxyl groups of Ser149 and Tyr183. Collapse of the tetrahedral intermediate is then followed by C-S bond cleavage and protonation of the CoA thiolate, in the presence of NADP+, there is very low affinity for the CoA ester compounds, which precludes the formation of a nonproductive complex, catalytic mechanism and substrate specificity, overview
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
redox reaction
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reduction
oxidation
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reduction
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PATHWAY SOURCE
PATHWAYS
BRENDA
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SYSTEMATIC NAME
IUBMB Comments
cinnamaldehyde:NADP+ oxidoreductase (CoA-cinnamoylating)
Acts also on a number of substituted cinnamoyl esters of coenzyme A.
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CAS REGISTRY NUMBER
COMMENTARY
59929-39-4
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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
4-coumaroyl-CoA + NADPH + H+
4-coumaric aldehyde + CoA + NADP+
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?
coumaroyl-CoA + NADPH + H+
coumaraldehyde + CoA + NADP+
activity assay
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-
?
4-coumaroyl-CoA + NADPH + H+
4-coumaraldehyde + CoA + NADP+
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-
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r
4-coumaroyl-CoA + NADPH + H+
4-coumaraldehyde + CoA + NADP+
low activity
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r
4-coumaroyl-CoA + NADPH + H+
4-coumaraldehyde + CoA + NADP+
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-
-
?
4-coumaroyl-CoA + NADPH + H+
4-coumaraldehyde + CoA + NADP+
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-
-
r
4-coumaroyl-CoA + NADPH + H+
4-coumaraldehyde + CoA + NADP+
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-
-
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?
4-coumaroyl-CoA + NADPH + H+
4-coumaraldehyde + CoA + NADP+
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-
-
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?
4-coumaroyl-CoA + NADPH + H+
4-coumaraldehyde + CoA + NADP+
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-
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r
4-coumaroyl-CoA + NADPH + H+
4-coumaraldehyde + CoA + NADP+
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-
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?
4-coumaroyl-CoA + NADPH + H+
4-coumaraldehyde + CoA + NADP+
chimeric 4CL1-CCR fusion enzyme
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?
4-coumaroyl-CoA + NADPH + H+
4-coumaraldehyde + CoA + NADP+
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?
4-coumaroyl-CoA + NADPH + H+
4-coumaroylaldehyde + CoA + NADP+
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-
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r
4-coumaroyl-CoA + NADPH + H+
4-coumaroylaldehyde + CoA + NADP+
preferenced substrate
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r
5-hydroxyferuloyl-CoA + NADPH + H+
5-hydroxyconiferaldehyde + CoA + NADP+
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-
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?
5-hydroxyferuloyl-CoA + NADPH + H+
5-hydroxyconiferaldehyde + CoA + NADP+
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-
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?
5-hydroxyferuloyl-CoA + NADPH + H+
5-hydroxyconiferaldehyde + CoA + NADP+
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-
-
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?
5-hydroxyferuloyl-CoA + NADPH + H+
5-hydroxyconiferaldehyde + CoA + NADP+
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?
5-hydroxyferuloyl-CoA + NADPH + H+
5-hydroxyconiferaldehyde + CoA + NADP+
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?
5-hydroxyferuloyl-CoA + NADPH + H+
5-hydroxyferulic aldehyde + CoA + NADP+
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low activity
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?
5-hydroxyferuloyl-CoA + NADPH + H+
5-hydroxyferulic aldehyde + CoA + NADP+
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i.e. 4,5-dihydroxy-3-methoxycinnamoyl-CoA
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?
5-hydroxyferuloyl-CoA + NADPH + H+
5-hydroxyferulic aldehyde + CoA + NADP+
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i.e. 4,5-dihydroxy-3-methoxycinnamoyl-CoA
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?
5-hydroxyferuloyl-CoA + NADPH + H+
5-hydroxyferulic aldehyde + CoA + NADP+
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r
5-hydroxyferuloyl-CoA + NADPH + H+
5-hydroxyferulic aldehyde + CoA + NADP+
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?
caffeoyl-CoA + NADPH
caffeic aldehyde + CoA + NADP+
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poor substrate
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?
caffeoyl-CoA + NADPH + H+
caffealdehyde + CoA + NADP+
low activity
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r
caffeoyl-CoA + NADPH + H+
caffealdehyde + CoA + NADP+
low activity
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r
caffeoyl-CoA + NADPH + H+
caffealdehyde + CoA + NADP+
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preferred substrate for isoform CCR2
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r
caffeoyl-CoA + NADPH + H+
caffealdehyde + CoA + NADP+
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?
caffeoyl-CoA + NADPH + H+
caffealdehyde + CoA + NADP+
chimeric 4CL1-CCR fusion enzyme
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?
caffeoyl-CoA + NADPH + H+
caffealdehyde + CoA + NADP+
activity assay
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?
caffeoyl-CoA + NADPH + H+
caffeolylaldehyde + CoA + NADP+
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r
caffeoyl-CoA + NADPH + H+
caffeolylaldehyde + CoA + NADP+
preferenced substrate
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r
caffeoyl-CoA + NADPH + H+
caffeylaldehyde + NADP+
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?
cinnamaldehyde + CoA + NADP+
cinnamoyl-CoA + NADPH + H+
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?
cinnamaldehyde + CoA + NADP+
cinnamoyl-CoA + NADPH + H+
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?
cinnamoyl-CoA + NADPH
cinnamaldehyde + CoA + NADP+
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?
cinnamoyl-CoA + NADPH
cinnamaldehyde + CoA + NADP+
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low activity
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?
cinnamoyl-CoA + NADPH
cinnamaldehyde + CoA + NADP+
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catalyzes preferentially the formation of cinnamaldehyde
catalyzes preferentially the formation of cinnamaldehyde
?
cinnamoyl-CoA + NADPH + H+
cinnamaldehyde + CoA + NADP+
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?
coumaroyl-CoA + NADPH + H+
coumaric aldehyde + CoA + NADP+
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preferred substrate for isoform CCR2
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?
feruloyl-CoA + NADPH + H+
coniferaldehyde + CoA + NADP+
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best substrate
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r
feruloyl-CoA + NADPH + H+
coniferaldehyde + CoA + NADP+
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best substrate
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r
feruloyl-CoA + NADPH + H+
coniferaldehyde + CoA + NADP+
highly preferred substrate
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r
feruloyl-CoA + NADPH + H+
coniferaldehyde + CoA + NADP+
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?
feruloyl-CoA + NADPH + H+
coniferaldehyde + CoA + NADP+
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best substrate
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r
feruloyl-CoA + NADPH + H+
coniferaldehyde + CoA + NADP+
best substrate
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?
feruloyl-CoA + NADPH + H+
coniferaldehyde + CoA + NADP+
best substrate
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r
feruloyl-CoA + NADPH + H+
coniferaldehyde + CoA + NADP+
most favoured substrate