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Information on EC 3.1.1.49 - sinapine esterase and Organism(s) Brassica napus and UniProt Accession Q3ZFI4

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EC Tree
     3 Hydrolases
         3.1 Acting on ester bonds
             3.1.1 Carboxylic-ester hydrolases
                3.1.1.49 sinapine esterase
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This record set is specific for:
Brassica napus
UNIPROT: Q3ZFI4 not found.
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The taxonomic range for the selected organisms is: Brassica napus
The enzyme appears in selected viruses and cellular organisms
Synonyms
bnlip2, sinapine esterase, bnsce3, bnsce3/bnlip2, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
BnSCE3/BnLIP2
-
aromatic choline esterase
-
-
-
-
BnSCE3
-
-
esterase, sinapine
-
-
-
-
sinapine esterase
-
-
sinapoylcholine(sinapine) esterase
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hydrolysis of carboxylic ester
-
-
-
-
SYSTEMATIC NAME
IUBMB Comments
sinapoylcholine sinapohydrolase
-
CAS REGISTRY NUMBER
COMMENTARY hide
72506-67-3
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
3-phenylpropionylcholine + H2O
3-phenylpropionate + choline
show the reaction diagram
-
-
-
?
4-coumaroylcholine + H2O
coumaric acid + choline
show the reaction diagram
20% of activity with sinapoylcholine
-
-
?
benzoylcholine + H2O
benzoate + choline
show the reaction diagram
18% of activity with sinapoylcholine
-
-
?
caffeoylcholine
caffeic acid + choline
show the reaction diagram
25% of activity with sinapoylcholine
-
-
?
cinnamoylcholine + H2O
cinnamic acid + choline
show the reaction diagram
51% of activity with sinapoylcholine
-
-
?
feruloylcholine + H2O
ferulic acid + choline
show the reaction diagram
37% of activity with sinapoylcholine
-
-
?
sinapoylcholine + H2O
sinapic acid + choline
show the reaction diagram
isoferuloylcholine + H2O
isoferulic acid + choline
show the reaction diagram
-
-
-
-
?
O-sinapoylcholine + H2O
choline + sinapate
show the reaction diagram
-
i.e. sinapine
-
-
?
p-coumaroylcholine
p-coumaric acid + choline
show the reaction diagram
-
-
-
-
?
sinapoylcholine + H2O
sinapic acid + choline
show the reaction diagram
-
-
-
-
?
additional information
?
-
-
BnSCE3 reveals a broad substrate specificity toward phenolic choline esters, even accepting phosphatidylcholine, pointing to a phospholipase A-like activity
-
-
?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
sinapoylcholine + H2O
sinapic acid + choline
show the reaction diagram
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
-
-
?
O-sinapoylcholine + H2O
choline + sinapate
show the reaction diagram
-
i.e. sinapine
-
-
?
additional information
?
-
-
BnSCE3 reveals a broad substrate specificity toward phenolic choline esters, even accepting phosphatidylcholine, pointing to a phospholipase A-like activity
-
-
?
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Phenylmethylsulfonylfluoride
50% inhibition at about 8 mM PMSF
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.101
3-phenylpropionylcholine
30°C, pH 8.5
0.011
Cinnamoylcholine
30°C, pH 8.5
0.0026
Sinapoylcholine
30°C, pH 8.5
0.0039
isoferuloylcholine
-
cv. Gulliver
0.0037 - 0.0039
p-Coumaroylcholine
0.0104 - 0.0115
Sinapoylcholine
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
SwissProt
Manually annotated by BRENDA team
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
-
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
physiological function
additional information
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
SCE3_BRANA
389
0
43319
Swiss-Prot
Secretory Pathway (Reliability: 1)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
44000
1 * 44000, SDS-PAGE
47000
gel filtration
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
1 * 44000, SDS-PAGE
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
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
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Nicotiana benthamiana leaves
expression of BnSCE3 under the control of a seed-specific promoter in seeds
-
functional expression of Brassica napus BnSCE3 in Arabidopsis thaliana developing seeds resulting in a dramatic decrease in the sinapine content
-
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Larsen, L.M.; Nielsen, T.H.; Plger, A.; Sorensen, H.
Rapid and efficient method for the isolation and characterization of plant aromatic choline esterases
J. Chromatogr.
450
121-131
1988
Barbarea intermedia, Brassica napus, Brassica nigra, Brassica rapa subsp. oleifera, Sinapis alba
-
Manually annotated by BRENDA team
Clauss, K.; Baumert, A.; Nimtz, M.; Milkowski, C.; Strack, D.
Role of a GDSL lipase-like protein as sinapine esterase in Brassicaceae
Plant J.
53
802-813
2008
Brassica napus (Q3ZFI4), Brassica napus
Manually annotated by BRENDA team
Clauss, K.; von Roepenack-Lahaye, E.; Boettcher, C.; Roth, M.R.; Welti, R.; Erban, A.; Kopka, J.; Scheel, D.; Milkowski, C.; Strack, D.
Overexpression of sinapine esterase BnSCE3 in oilseed rape seeds triggers global changes in seed metabolism
Plant Physiol.
155
1127-1145
2011
Brassica napus
Manually annotated by BRENDA team
Milkowski, C.; Strack, D.
Sinapate esters in brassicaceous plants: biochemistry, molecular biology, evolution and metabolic engineering
Planta
232
19-35
2010
Arabidopsis thaliana (P0C8Z7), Arabidopsis thaliana (Q38894), Arabidopsis thaliana (Q3E7I6), Arabidopsis thaliana (Q9FPE4), Brassica napus
Manually annotated by BRENDA team