KEGG   ENZYME: 3.2.1.220
Entry
EC 3.2.1.220                Enzyme                                 
Name
ipecoside beta-D-glucosidase;
6-O-methyl-deacetylisoipecoside beta-glucosidase;
IpeGlu1
Class
Hydrolases;
Glycosylases;
Glycosidases, i.e. enzymes that hydrolyse O- and S-glycosyl compounds
Sysname
ipecoside glucohydrolase
Reaction(IUBMB)
(1) ipecoside + H2O = ipecoside aglycone + D-glucopyranose [RN:R13191];
(2) N-deacetylipecoside + H2O = N-deacetylipecoside aglycone + D-glucopyranose [RN:R13253];
(3) 6-O-methyl-N-deacetylipecoside + H2O = 6-O-methyl-N-deacetylipecoside aglycone + D-glucopyranose [RN:R13254]
Reaction(KEGG)
R13191 R13253 R13254;
(other) R11682
Substrate
ipecoside [CPD:C09464];
H2O [CPD:C00001];
N-deacetylipecoside [CPD:C07307];
6-O-methyl-N-deacetylipecoside [CPD:C22883]
Product
ipecoside aglycone [CPD:C22694];
D-glucopyranose [CPD:C00031];
N-deacetylipecoside aglycone [CPD:C22882];
6-O-methyl-N-deacetylipecoside aglycone [CPD:C22884]
Comment
The enzyme, isolated from the roots of the plant Carapichea ipecacuanha, preferentially hydrolyses glucosidic ipecoside alkaloids except for their lactams, but shows poor or no activity toward other substrates. IpeGlu1 activity is extremely poor toward 7-O-methyl and 6,7-O,O-dimethyl derivatives. However, 6-O-methyl derivatives are hydrolysed as efficiently as non-methylated substrates. IpeGlu1 accepts both 1alpha(S)-N-deacetylisoipecoside and 1beta(R)-N-deacetylipecoside epimers as substrate, with preference for the 1beta(R)-epimer. 6-O-methyl-N-deacetylisoipecoside is an intermediate in the biosynthesis of the medicinal alkaloid emetine.
History
EC 3.2.1.220 created 2023
Pathway
ec00950  Isoquinoline alkaloid biosynthesis
Orthology
K22092  ipecoside beta-D-glucosidase
Reference
1  [PMID:18927081]
  Authors
Nomura T, Quesada AL, Kutchan TM
  Title
The new beta-D-glucosidase in terpenoid-isoquinoline alkaloid biosynthesis in Psychotria ipecacuanha.
  Journal
J Biol Chem 283:34650-9 (2008)
DOI:10.1074/jbc.M806953200
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 3.2.1.220
IUBMB Enzyme Nomenclature: 3.2.1.220
ExPASy - ENZYME nomenclature database: 3.2.1.220
BRENDA, the Enzyme Database: 3.2.1.220
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