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1,2-di-O-sinapoyl-beta-D-glucose + choline
2-O-sinapoyl-beta-D-glucose + sinapoylcholine
1-feruloyl-beta-D-glucose + choline
D-glucose + feruloylcholine
1-O-caffeoyl-beta-D-glucose + choline
beta-D-glucose + caffeoylcholine
-
-
-
-
?
1-O-feruloyl-beta-D-glucose + choline
beta-D-glucose + feruloylcholine
-
-
-
-
?
1-O-sinapoyl-beta-D-glucose + 2-methylaminoethanol
beta-D-glucose + sinapoyl-2-methylaminoethanol
-
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
beta-D-glucose + sinapoylcholine
-
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
1-O-sinapoyl-beta-D-glucose + N,N-dimethylethanolamine
beta-D-glucose + sinapoyl-N,N-dimethylethanolamine
-
-
-
-
?
1-O-sinapoyl-beta-D-glucose + neopentyl alcohol
beta-D-glucose + neopentylsinapate
-
-
-
-
?
1-O-sinapoyl-beta-D-glucose + Tris
?
-
-
-
-
?
1-p-coumaroyl-beta-D-glucose + choline
D-glucose + p-coumaroylcholine
caffeoyl-beta-D-glucose + choline
D-glucose + caffeoylcholine
-
poor substrate
-
-
?
p-coumaroyl-beta-D-glucose + choline
beta-D-glucose + coumaroylcholine
-
-
-
-
?
1,2-di-O-sinapoyl-beta-D-glucose + choline
2-O-sinapoyl-beta-D-glucose + sinapoylcholine
-
best donor substrate
-
-
?
1,2-di-O-sinapoyl-beta-D-glucose + choline
2-O-sinapoyl-beta-D-glucose + sinapoylcholine
-
best donor substrate
-
-
?
1-feruloyl-beta-D-glucose + choline
D-glucose + feruloylcholine
-
40% as active as 1-sinapoylglucose
-
-
?
1-feruloyl-beta-D-glucose + choline
D-glucose + feruloylcholine
-
-
-
-
?
1-feruloyl-beta-D-glucose + choline
D-glucose + feruloylcholine
-
40% as active as 1-sinapoylglucose
-
-
?
1-feruloyl-beta-D-glucose + choline
D-glucose + feruloylcholine
-
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
enzyme functions in sinapate ester synthesis
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
i.e. sinapine
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
i.e. sinapine
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
i.e. sinapine
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
no acceptors are betaine or CDP-choline
i.e. sinapine
ir
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
specific for 1-O-sinapoyl-beta-glucose
i.e. sinapine
ir
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
i.e. sinapine
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
Camelina sp.
-
-
i.e. sinapine
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
i.e. sinapine
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
Cheiranthus sp.
-
-
i.e. sinapine
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
i.e. sinapine
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
i.e. sinapine
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
i.e. sinapine
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
Lepidium sp.
-
-
i.e. sinapine
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
Malcomia africana
-
-
i.e. sinapine
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
i.e. sinapine
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
i.e. sinapine
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
i.e. sinapine
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
i.e. sinapine
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
no donors are 1-benzoylglucose, 1-galloylglucose, 6-sinapoylglucose, 3-sinapoylfructose
i.e. sinapine
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
absolute acceptor specificity towards choline
i.e. sinapine
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
absolute acceptor specificity towards choline
i.e. sinapine
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
ethanolamine, myo-inositol, citric, L-malic, L-tartaric, quinic or shikimic acid are no acceptors
i.e. sinapine
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
involved in sinapine biosynthesis
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
i.e. sinapine
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
Rorippa sp.
-
-
i.e. sinapine
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
i.e. sinapine
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
no donors are 1-benzoylglucose, 1-galloylglucose, 6-sinapoylglucose, 3-sinapoylfructose
i.e. sinapine
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
absolute acceptor specificity towards choline
i.e. sinapine
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
involved in sinapine biosynthesis
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
i.e. sinapine
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
Sisymbrium sp.
-
-
i.e. sinapine
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
i.e. sinapine
?
1-p-coumaroyl-beta-D-glucose + choline
D-glucose + p-coumaroylcholine
-
25%
-
-
?
1-p-coumaroyl-beta-D-glucose + choline
D-glucose + p-coumaroylcholine
-
poor substrate
-
-
?
1-p-coumaroyl-beta-D-glucose + choline
D-glucose + p-coumaroylcholine
-
13%
-
-
?
1-p-coumaroyl-beta-D-glucose + choline
D-glucose + p-coumaroylcholine
-
-
-
-
?
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1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
enzyme functions in sinapate ester synthesis
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
Camelina sp.
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
Cheiranthus sp.
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
Lepidium sp.
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
Malcomia africana
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
involved in sinapine biosynthesis
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
Rorippa sp.
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
involved in sinapine biosynthesis
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
Sisymbrium sp.
-
-
-
?
1-O-sinapoyl-beta-D-glucose + choline
D-glucose + sinapoylcholine
-
-
-
?
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evolution
evolutionary ancestry of the sinapoyltransferases sinapoylglucose:L-malate sinapoyltransferase and sinapoylglucose:choline sinapoyltransferase with serine carboxypeptidases, molecular mechanisms, overview
evolution
-
evolutionary ancestry of the sinapoyltransferases sinapoylglucose:L-malate sinapoyltransferase and sinapoylglucose:choline sinapoyltransferase with serine carboxypeptidases, molecular mechanisms, overview. Phylogenetic clustering of the sinapoyltransferases SMT and SCT and of sinapine esterase BnSCE3
malfunction
a T-DNA insertion mutant lacking SCT activity reveals increased betaine levels in seeds due to increased endogenous choline supply as a consequence of blocked sinapine synthesis
malfunction
-
down-regulation of BnSCT is accompanied by an increase in the level of free choline that is not channelled into sinapine
metabolism
1-O-sinapoylglucose, produced by UDP-glucose:sinapate glucosyltransferase, SGT EC 2.4.1.120, during seed development, is converted to sinapine by sinapoylglucose:choline sinapoyltransferase, SCT, and hydrolyzed by sinapoylcholine (sinapine) esterase, SCE, in germinating seeds. The released sinapate feeds via sinapoylglucose into the biosynthesis of sinapoylmalate in the seedlings catalyzed by sinapoylglucose:L-malate sinapoyltransferase, SMT, pathway of sinapate ester biosynthesis, overview. The metabolic pool size of sinapoylglucose in brassicaceous plants is dependent on its turnover rate, developmentally regulated via differential expression of enzymes involved
metabolism
-
1-O-sinapoylglucose, produced by UDP-glucose:sinapate glucosyltransferase, SGT, during seed development, is converted to sinapine by sinapoylglucose:choline sinapoyltransferase , SCT, and hydrolyzed by sinapoylcholine (sinapine) esterase, SCE, in germinating seeds. The released sinapate feeds via sinapoylglucose into the biosynthesis of sinapoylmalate in the seedlings catalyzed by sinapoylglucose:L-malate sinapoyltransferase, SMT, pathway of sinapate ester biosynthesis, overview. The metabolic pool size of sinapoylglucose in brassicaceous plants is dependent on its turnover rate, developmentally regulated via differential expression of enzymes involved
physiological function
-
in brassicaceous plants like Arabidpsis thaliana and Brassica napus sinapate is channelled via 1-O-sinapoyl-beta-glucose to various sinapate esters of which 2-O-sinapoyl-L-malate, a proven UV-shielding component, partially accumulates in vacuoles of the leaf epidermis
physiological function
in brassicaceous plants like Arabidpsis thaliana and Brassica napus sinapate is channelled via 1-O-sinapoyl-beta-glucose to various sinapate esters of which 2-O-sinapoyl-L-malate, a proven UV-shielding component, partially accumulates in vacuoles of the leaf epidermis
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Grwe, W.; Strack, D.
Partial purification and some properties of 1-sinapoylglucose: choline sinapoyltransferase (sinapine synthase) from seeds of Raphanus sativus L. and Sinapis alba L.
Z. Naturforsch. C
41
28-33
1986
Raphanus sativus, Sinapis alba
-
brenda
Strack, D.; Knogge, W.; Dahlbender, B.
Enzymatic synthesis of sinapine from 1-O-sinapoyl-beta-D-glucose and choline by a cell-free system from developing seeds of red radish (Raphanus sativus L. var. sativus)
Z. Naturforsch. C
38
21-27
1982
Raphanus sativus
-
brenda
Vogt, T.; Aebershold, R.; Ellis, B.
Purification and characterization of sinapine synthase from seeds of Brassica napus
Arch. Biochem. Biophys.
300
622-628
1993
Brassica napus
brenda
Regenbrecht, J.; Strack, D.
Distribution of 1-sinapoylglucose:choline sinapoyltransferase activity in the Brassicaceae
Phytochemistry
24
407-410
1985
Berteroa incana, Biscutella lyrata, Brassica napus, Brassica sp., Camelina sp., Capsella bursa-pastoris, Cheiranthus sp., Descurainia sophia, Eruca vesicaria subsp. sativa, Isatis tinctoria, Lepidium sp., Malcomia africana, Matthiola incana, Neslia paniculata, Raphanus sativus, Raphanus raphanistrum, Rapistrum rugosum, Rorippa sp., Sinapis alba, Sinapis arvensis, Sisymbrium sp., Turritis glabra
-
brenda
Shirley, A.M.; Chapple, C.
Biochemical characterization of sinapoylglucose:choline sinapoyltransferase, a serine carboxypeptidase-like protein that functions as an acyltransferase in plant secondary metabolism
J. Biol. Chem.
278
19870-19877
2003
Arabidopsis sp.
brenda
Milkowski, C.; Baumert, A.; Schmidt, D.; Nehlin, L.; Strack, D.
Molecular regulation of sinapate ester metabolism in Brassica napus: expression of genes, properties of the encoded proteins and correlation of enzyme activities with metabolite accumulation
Plant J.
38
80-92
2004
Brassica napus
brenda
Stehle, F.; Brandt, W.; Milkowski, C.; Strack, D.
Structure determinants and substrate recognition of serine carboxypeptidase-like acyltransferases from plant secondary metabolism
FEBS Lett.
580
6366-6374
2006
Brassica napus (Q6TXD6), Arabidopsis thaliana (Q8VZU3)
brenda
Fraser, C.M.; Rider, L.W.; Chapple, C.
An expression and bioinformatics analysis of the Arabidopsis serine carboxypeptidase-like gene family
Plant Physiol.
138
1136-1148
2005
Arabidopsis thaliana (Q8VZU3)
brenda
Weier, D.; Mittasch, J.; Strack, D.; Milkowski, C.
The genes BnSCT1 and BnSCT2 from Brassica napus encoding the final enzyme of sinapine biosynthesis: molecular characterization and suppression
Planta
227
375-385
2008
Brassica napus (A4VB84), Brassica napus (A4VB85), Brassica napus
brenda
Huang, J.; Rozwadowski, K.; Bhinu, V.S.; Schaefer, U.; Hannoufa, A.
Manipulation of sinapine, choline and betaine accumulation in Arabidopsis seed: Towards improving the nutritional value of the meal and enhancing the seedling performance under environmental stresses in oilseed crops
Plant Physiol. Biochem.
46
647-654
2008
Arabidopsis thaliana (Q8VZU3)
brenda
Milkowski, C.; Strack, D.
Sinapate esters in brassicaceous plants: biochemistry, molecular biology, evolution and metabolic engineering
Planta
232
19-35
2010
Brassica napus, Arabidopsis thaliana (Q8VZU3), Arabidopsis thaliana
brenda