3.2.1.B16: ipecoside beta-D-glucosidase
This is an abbreviated version!
For detailed information about ipecoside beta-D-glucosidase, go to the full flat file.
Word Map on EC 3.2.1.B16
Reaction
Synonyms
Ipecac alkaloid beta-D-glucosidase, IpeGlu1
ECTree
3.2.1.B16 ipecoside beta-D-glucosidaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 3.2.1.B16 - ipecoside beta-D-glucosidase
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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
1alpha(S)-6-O-methyl-N-deacetylisoipecoside + H2O
1alpha(S)-6-O-methyl-N-deacetylisoipecoside aglycone + D-glucose
kcat/KM is 16.3% of the value for 1beta(R)-N-deacetylipecoside
-
-
?
1alpha(S)-N-deacetylisoipecoside + H2O
1alpha(S)-N-deacetylisoipecoside aglycone + D-glucose
kcat/KM is 16.9% of the value for 1beta(R)-N-deacetylipecoside
-
-
?
1beta(R)-6-O-methyl-N-deacetylipecoside + H2O
1beta(R)-6-O-methyl-N-deacetylipecoside aglycone + D-glucose
vincoside + H2O
vincoside aglycone + D-glucose
kcat/KM is 11.1% of the value for 1beta(R)-N-deacetylipecoside
-
-
?
1beta(R)-6-O-methyl-N-deacetylipecoside + H2O
1beta(R)-6-O-methyl-N-deacetylipecoside aglycone + D-glucose
the enzyme is involved in alkaloid biosynthesis
-
-
?
1beta(R)-6-O-methyl-N-deacetylipecoside + H2O
1beta(R)-6-O-methyl-N-deacetylipecoside aglycone + D-glucose
kcat/KM is 90.5% of the value for 1beta(R)-N-deacetylipecoside
-
-
?
1beta(R)-N-deacetylipecoside + H2O
1beta(R)-N-deacetylipecoside aglycone + D-glucose
the 1beta(R)-epimer N-deacetylipecoside is the precursor mainly of ipecoside and alangiside, the alkaloidal glucosides having a beta-configuration
-
-
?
1beta(R)-N-deacetylipecoside + H2O
1beta(R)-N-deacetylipecoside aglycone + D-glucose
IpeGlu1 preferentially hydrolyzes glucosidic Ipecac alkaloids except for their lactams, but shows poor or no activity toward other substrates, including terpenoid-indole alkaloid glucosides. IpeGlu1 activity is extremely poor toward 7-O-methyl and 6,7-O,O-dimethyl derivatives. However, 6-O-methyl derivatives are hydrolyzed as efficiently as non-methylated substrates. IpeGlu1 accepts both 1alpha(S)-N-deacetylisoipecoside and 1beta(R)-N-deacetylipecoside epimers as substrate with preference of 1beta(R)-epimer to 1alpha(S)-epimer
spontaneous transitions of the highly reactive aglycon. A possible mechanism is as follows: the hemiacetal aglycon forms a dialdehyde by ring opening, and the N-atom attacks the carbolyl group of the aldehyde, followed by dehydration to form an iminium cation which is considered to tautomerize to the enamine form
-
?
ipecoside + H2O
ipecoside aglycone + D-glucose
the enzyme is involved in alkaloid biosynthesis
-
-
?
ipecoside + H2O
ipecoside aglycone + D-glucose
kcat/KM is 5.2fold higher than the value for 1beta(R)-N-deacetylipecoside
-
-
?
additional information
?
-
no activity with raucaffricine. IpeGlu1 does not accept the lactams, demethylisoalangiside and demethylalangiside, as substrate
-
-
?
additional information
?
-
-
no activity with raucaffricine. IpeGlu1 does not accept the lactams, demethylisoalangiside and demethylalangiside, as substrate
-
-
?
