Information on EC 3.2.1.105 - 3alpha(S)-strictosidine beta-glucosidase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
3.2.1.105
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RECOMMENDED NAME
GeneOntology No.
3alpha(S)-strictosidine beta-glucosidase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
strictosidine + H2O = D-glucose + strictosidine aglycone
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hydrolysis of O-glycosyl bond
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
ajmaline and sarpagine biosynthesis
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Biosynthesis of secondary metabolites
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Indole alkaloid biosynthesis
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Metabolic pathways
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SYSTEMATIC NAME
IUBMB Comments
strictosidine beta-D-glucohydrolase
Does not act on a number of closely related glycosides. Strictosidine is a precursor of indole alkaloids.
CAS REGISTRY NUMBER
COMMENTARY hide
73379-57-4
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
weak activity
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-
Manually annotated by BRENDA team
Amsonia salicifolia
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-
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Manually annotated by BRENDA team
Catharanthus pusillus
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-
-
Manually annotated by BRENDA team
weak activity
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-
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
weak activity
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-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
18,19-dihydrostrictosidine + H2O
D-glucose + 18,19-dihydrostrictosidine aglycone
show the reaction diagram
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-
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?
5-methylstrictosidine + H2O
D-glucose + 5-methylstrictosidine aglycone
show the reaction diagram
-
-
-
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?
5alpha-carboxystrictosidine + H2O
D-glucose + 5alpha-carboxystrictosidine aglycone
show the reaction diagram
-
-
-
?
6-fluorostrictosidine + H2O
D-glucose + 6-fluorostrictosidine aglycone
show the reaction diagram
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-
-
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?
6-methoxystrictosidine + H2O
D-glucose + 6-methoxystrictosidine aglycone
show the reaction diagram
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-
-
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?
6-methylstrictosidine + H2O
D-glucose + 6-methylstrictosidine aglycone
show the reaction diagram
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-
-
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?
7-fluorostrictosidine + H2O
D-glucose + 7-fluorostrictosidine aglycone
show the reaction diagram
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-
-
-
?
7-methoxystrictosidine + H2O
D-glucose + 7-methoxystrictosidine aglycone
show the reaction diagram
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-
-
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?
7-methylstrictosidine + H2O
D-glucose + 7-methylstrictosidine aglycone
show the reaction diagram
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-
-
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?
8-methylstrictosidine + H2O
D-glucose + 8-methylstrictosidine aglycone
show the reaction diagram
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-
-
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?
dolichantoside + H2O
?
show the reaction diagram
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-
-
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dolichantoside + H2O
D-glucose + dolichantoside aglycone
show the reaction diagram
Nbeta-acetylstrictosidine + H2O
D-glucose + Nbeta-acetylstrictosidine aglycone
show the reaction diagram
weak substrate
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?
Nbeta-methylstrictosidine + H2O
D-glucose + Nbeta-methylstrictosidine aglycone
show the reaction diagram
weak substrate
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?
palicoside + H2O
?
show the reaction diagram
palicoside + H2O
D-glucose + palicoside aglycone
show the reaction diagram
strictosidine
?
show the reaction diagram
strictosidine + H2O
cathenamine
show the reaction diagram
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-
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?
strictosidine + H2O
D-glucose + strictosidine aglycone
show the reaction diagram
vincoside + H2O
?
show the reaction diagram
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hydrolyzed at less than 10% of strictosidine
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vincoside + H2O
D-glucose + vincoside aglycone
show the reaction diagram
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-
-
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?
vincoside pent-4-yn-1-yl ester + H2O
D-glucose + vincoside pent-4-yn-1-yl ester aglycone
show the reaction diagram
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-
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?
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
strictosidine
?
show the reaction diagram
strictosidine + H2O
D-glucose + strictosidine aglycone
show the reaction diagram
additional information
?
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involved In the indole alkaloid biosynthesis by hydrolyzing strictosidine to cathenamine
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
D(+)-gluconic acid delta-lactone
D-gluconolactone
serpentine
strictosidine
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enzyme I shows substrate inhibition at 1 mM, enzyme II not
tryptamine
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2.5 mM, 15% inhibition of enzyme I and II
additional information
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enzyme activity is not inhibited by raucaffricine
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.22
5-methylstrictosidine
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pH 6.0, 37C
0.15
6-fluorostrictosidine
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pH 6.0, 37C
0.37
6-methoxystrictosidine
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pH 6.0, 37C
0.071
6-methylstrictosidine
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pH 6.0, 37C
0.12
7-fluorostrictosidine
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pH 6.0, 37C
0.43
7-methoxystrictosidine
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pH 6.0, 37C
0.092
7-methylstrictosidine
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pH 6.0, 37C
0.14
8-methylstrictosidine
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pH 6.0, 37C
0.564 - 1.13
dolichantoside
0.335 - 7.015
palicoside
0.01 - 10
strictosidine
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.5 - 5
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enzyme form SGI, a second pH-optimum at pH 7.0
6 - 6.4
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enzyme I and II
7
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enzyme form SGI, a second pH-optimum at pH 4.5-5.0
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.2 - 8
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50% of maximal activity at oH 4.2, above pH 5.2 the activity slowly decreases up to pH 8
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6
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calculated from amino acid sequence
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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; stem
Manually annotated by BRENDA team
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abaxial and adaxial
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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most likely associated with endoplasmic reticulum
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
22000
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enzyme form SGII, non-denaturing PAGE
31000
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enzyme form SGIII, non-denaturing PAGE
63000
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x * 63000, SDS-PAGE
80000
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2 * 80000, SDS-PAGE; x * 80000, SDS-PAGE
187000
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enzyme form SGII, non-denaturing PAGE
190000
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enzyme form SGII, non-denaturing PAGE
200000
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native PAGE; non-denaturing PAGE
230000
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enzyme I, gel filtration
250000
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enzyme form I, non-denaturing PAGE
450000
500000
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enzyme form II, non-denaturing PAGE
630000
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enzyme form III, non-denaturing PAGE
650000
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native PAGE
670000
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above, enzyme form SGI, gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
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2 * 80000, SDS-PAGE
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
2.48 A resolution, sitting- and hanging-drop vapour diffusion, 0.3 M ammonium sulfate, 0.1 M sodium acetate, pH 4.6, 10% PEG 4000
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
50
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stable at
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
highly increased sensitivity for freezing and thawing after separation over Superose 6
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-80C, 50% loss of activity
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-80C, stable for 6 months
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4C, 24 h, stable
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
3 different enzyme forms
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Ni-NTA column, dipeptidyl aminopeptidase, Mono Q column
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partial, three enzyme forms: SGI, SGII and SGIII
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli strain JM109
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expressed in Nicotiana tabacum
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expression in Escherichia coli
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expression in Escherichia coli M15 cells, functional co-expression with strictosidine synthase; functional co-expression in Escherichia coli strain M15 with strictosidine synthase, EC 4.3.3.2, resulting in cathenamine formation from administered tryptamine and secologanin
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expression in Escherichia coli strain Top 10 with His-tag
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expression in Saccharomyces cerevisiae
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fusion protein with intein tag, expressed in Escherichia coli
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
after elicitation with H2O2 or buthionine sulfoximine plus jasmonic acid the enzyme activity increases by 2.8 or 4.2fold, respectively. Enzyme transcript is also upregulated
elicitation of suspension cultures with methyl jasmonate and Pythium aphanidermatum homogenate causes transcriptional upregulation of SGD and enhances the accumulation of total alkaloids
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the enzyme is significant upregulated in plants experimentally and naturally infected with Spiroplasma citri
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
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plays central role in indole alkaloid biosynthesis