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Enzyme Nomenclature
Information on EC 3.1.1.49 - sinapine esterase
for references in articles please use BRENDA:EC3.1.1.49
Word Map on EC 3.1.1.49
- 3.1.1.49
- seedlings
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brassica
- napus
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lipases
- sinapate
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antinutritive
- brassicaceae
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sinapoylmalate
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
3.1.1.49
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RECOMMENDED NAME
GeneOntology No.
sinapine esterase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
sinapoylcholine + H2O = sinapate + choline
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hydrolysis of carboxylic ester
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
sinapoylcholine sinapohydrolase
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CAS REGISTRY NUMBER
COMMENTARY
72506-67-3
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
metabolism
physiological function
additional information
evolution
sinapine esterase is classifed as a member of the SGNH hydrolase subfamily of GDSL-lipases which cleave ester bonds in a wide array of lipids; sinapine esterase is classifed as a member of the SGNH hydrolase subfamily of GDSL-lipases which cleave ester bonds in a wide array of lipids; sinapine esterase is classifed as a member of the SGNH hydrolase subfamily of GDSL-lipases which cleave ester bonds in a wide array of lipids; sinapine esterase is classifed as a member of the SGNH hydrolase subfamily of GDSL-lipases which cleave ester bonds in a wide array of lipids
evolution
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BnSCE3 is classifed as a member of the SGNH hydrolase subfamily of GDSL-lipases which cleave ester bonds in a wide array of lipids. Sinapine esterase BnSCE3 kept the catalytic mechanism of the hydrolytic ancestor but experienced a change in substrate specificity
metabolism
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a portion of choline enters the phospholipid metabolism, and sinapate is routed via 1-O-sinapoyl-beta-D-glucose into sinapoylmalate
metabolism
1-O-sinapoylglucose, produced by UDP-glucose:sinapate glucosyltransferase during seed development, is converted to sinapine by sinapoylglucose:choline sinapoyltransferase and hydrolyzed by sinapoylcholine (sinapine) esterase in germinating seeds. The released sinapate feeds via sinapoylglucose into the biosynthesis of sinapoylmalate in the seedlings catalyzed by sinapoylglucose:L-malate sinapoyltransferase. Pathway of sinapate ester biosynthesis, overview; 1-O-sinapoylglucose, produced by UDP-glucose:sinapate glucosyltransferase during seed development, is converted to sinapine by sinapoylglucose:choline sinapoyltransferase and hydrolyzed by sinapoylcholine (sinapine) esterase in germinating seeds. The released sinapate feeds via sinapoylglucose into the biosynthesis of sinapoylmalate in the seedlings catalyzed by sinapoylglucose:L-malate sinapoyltransferase. Pathway of sinapate ester biosynthesis, overview; 1-O-sinapoylglucose, produced by UDP-glucose:sinapate glucosyltransferase during seed development, is converted to sinapine by sinapoylglucose:choline sinapoyltransferase and hydrolyzed by sinapoylcholine (sinapine) esterase in germinating seeds. The released sinapate feeds via sinapoylglucose into the biosynthesis of sinapoylmalate in the seedlings catalyzed by sinapoylglucose:L-malate sinapoyltransferase. Pathway of sinapate ester biosynthesis, overview; 1-O-sinapoylglucose, produced by UDP-glucose:sinapate glucosyltransferase during seed development, is converted to sinapine by sinapoylglucose:choline sinapoyltransferase and hydrolyzed by sinapoylcholine (sinapine) esterase in germinating seeds. The released sinapate feeds via sinapoylglucose into the biosynthesis of sinapoylmalate in the seedlings catalyzed by sinapoylglucose:L-malate sinapoyltransferase. Pathway of sinapate ester biosynthesis, overview
metabolism
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1-O-sinapoylglucose, produced by UDP-glucose:sinapate glucosyltransferase during seed development, is converted to sinapine by sinapoylglucose:choline sinapoyltransferase and hydrolyzed by sinapoylcholine (sinapine) esterase in germinating seeds. The released sinapate feeds via sinapoylglucose into the biosynthesis of sinapoylmalate in the seedlings catalyzed by sinapoylglucose:L-malate sinapoyltransferase. Pathway of sinapate ester biosynthesis, overview
physiological function
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during early stages of seedling development, a sinapine esterase BnSCE3 hydrolyzes sinapine, releasing choline and sinapate, metabolic changes in developing seedlings of wild-type and enzyme overexpressing plants, overview
physiological function
sinapoylmalate is involved in protecting the leaves against the deleterious effects of UV-B radiation. Sinapine might function as storage vehicle for ready supply of choline for phosphatidylcholine biosynthesis in young seedlings; sinapoylmalate is involved in protecting the leaves against the deleterious effects of UV-B radiation. Sinapine might function as storage vehicle for ready supply of choline for phosphatidylcholine biosynthesis in young seedlings; sinapoylmalate is involved in protecting the leaves against the deleterious effects of UV-B radiation. Sinapine might function as storage vehicle for ready supply of choline for phosphatidylcholine biosynthesis in young seedlings; sinapoylmalate is involved in protecting the leaves against the deleterious effects of UV-B radiation. Sinapine might function as storage vehicle for ready supply of choline for phosphatidylcholine biosynthesis in young seedlings
physiological function
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sinapoylmalate is involved in protecting the leaves against the deleterious effects of UV-B radiation. Sinapine might function as storage vehicle for ready supply of choline for phosphatidylcholine biosynthesis in young seedlings. Antinutritive character of sinapine and related sinapate esters
additional information
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profiling of secondary metabolites and comparison in wild-type and transgenic seeds, overview
additional information
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SCE activity in seedlings of Brassica napus is mediated by a GDSL lipase-like enzyme designated as BnSCE3, one of three detected SCE isoforms
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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-coumaroylcholine + H2O
coumaric acid + choline
20% of activity with sinapoylcholine
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?
benzoylcholine + H2O
benzoate + choline
18% of activity with sinapoylcholine
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?
additional information
?
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BnSCE3 reveals a broad substrate specificity toward phenolic choline esters, even accepting phosphatidylcholine, pointing to a phospholipase A-like activity
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caffeoylcholine
caffeic acid + choline
25% of activity with sinapoylcholine
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?
cinnamoylcholine + H2O
cinnamic acid + choline
51% of activity with sinapoylcholine
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?
feruloylcholine + H2O
ferulic acid + choline
37% of activity with sinapoylcholine
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?
O-sinapoylcholine + H2O
choline + sinapate
i.e. sinapine
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?
sinapoylcholine + H2O
sinapic acid + choline
role for the GDSL lipase-like BnSCE3/BnLIP2 as a sinapine esterase, catalyzing hydrolysis of sinapine during seed germination, leading, via 1-O-sinapoyl-beta-glucose, to sinapoyl-L-malate in the seedlings
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?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
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
sinapoylcholine + H2O
sinapic acid + choline
Q3ZFI4
role for the GDSL lipase-like BnSCE3/BnLIP2 as a sinapine esterase, catalyzing hydrolysis of sinapine during seed germination, leading, via 1-O-sinapoyl-beta-glucose, to sinapoyl-L-malate in the seedlings
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?
additional information
?
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BnSCE3 reveals a broad substrate specificity toward phenolic choline esters, even accepting phosphatidylcholine, pointing to a phospholipase A-like activity
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O-sinapoylcholine + H2O
choline + sinapate
P0C8Z7, Q38894, Q3E7I6, Q9FPE4
i.e. sinapine
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?
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
germinating; germinating; germinating; germinating
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
functional expression of Brassica napus BnSCE3 in Arabidopsis thaliana developing seeds resulting in a dramatic decrease in the sinapine content
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gene At1g28640, the BnSCE3 homologue is tagged on chromosome I; gene At1g28650, the BnSCE3 homologue is tagged on chromosome I; gene At1g28660, the BnSCE3 homologue is tagged on chromosome I; gene At1g28670, the BnSCE3 homologue is tagged on chromosome I
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
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sinapine levels of transgenic seeds are less than 5% of wild-type levels, whereas choline levels are increased. Weight, size, and water content of transgenic seeds are significantly higher than those of wild-type seeds, phenotype, overveiw
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LINKS TO OTHER DATABASES (specific for EC-Number 3.1.1.49)
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