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Literature summary extracted from

  • Nomura, T.; Quesada, A.L.; Kutchan, T.M.
    The new beta-D-glucosidase in terpenoid-isoquinoline alkaloid biosynthesis in Psychotria ipecacuanha (2008), J. Biol. Chem., 283, 34650-34659.
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

EC Number Cloned (Comment) Organism
3.2.1.B16 recombinant IpeGlu1 is efficiently expressed in a soluble protein fraction in Eschericha coli PlusS strain, more than 50% of the expressed protein is precipitated as an inclusion body Carapichea ipecacuanha

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.2.1.B16 Ag+ 1 mM, 23% inhibition Carapichea ipecacuanha
3.2.1.B16 Co2+ 1 mM, 14% inhibition Carapichea ipecacuanha
3.2.1.B16 Cu2+ 1 mM, 50% inhibition Carapichea ipecacuanha
3.2.1.B16 Fe2+ 1 mM, 54% inhibition Carapichea ipecacuanha
3.2.1.B16 Mg2+ 1 mM, 20% inhibition Carapichea ipecacuanha
3.2.1.B16 Mn2+ 1 mM, 14% inhibition Carapichea ipecacuanha
3.2.1.B16 additional information EDTA and 2-mercaptoethanol do not affect the activity Carapichea ipecacuanha
3.2.1.B16 Ni2+ 1 mM, 19% inhibition Carapichea ipecacuanha
3.2.1.B16 Zn2+ 1 mM, 36% inhibition Carapichea ipecacuanha
3.2.1.21 Cu2+ 1 mM, 50% residual activity Carapichea ipecacuanha
3.2.1.21 Fe3+ 1 mM, 46% residual activity Carapichea ipecacuanha
3.2.1.21 additional information not inhibitory: EDTA, 2-mercaptoethanol Carapichea ipecacuanha
3.2.1.21 Zn2+ 1 mM, 64% residual activity Carapichea ipecacuanha

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
3.2.1.B16 0.1
-
 ipecoside pH 5.0, 30°C Carapichea ipecacuanha
3.2.1.B16 0.29
-
 vincoside pH 5.0, 30°C Carapichea ipecacuanha
3.2.1.B16 0.32
-
 1beta(R)-N-deacetylipecoside pH 5.0, 30°C Carapichea ipecacuanha
3.2.1.B16 0.39
-
 1beta(R)-6-O-methyl-N-deacetylipecoside pH 5.0, 30°C Carapichea ipecacuanha
3.2.1.B16 1.3
-
 1alpha(S)-6-O-methyl-N-deacetylisoipecoside pH 5.0, 30°C Carapichea ipecacuanha
3.2.1.B16 5.8
-
 1alpha(S)-N-deacetylisoipecoside pH 5.0, 30°C Carapichea ipecacuanha
3.2.1.21 0.1
-
 ipecoside pH 5.0, 30°C Carapichea ipecacuanha
3.2.1.21 0.19
-
 strictosidine pH 5.0, 30°C Carapichea ipecacuanha
3.2.1.21 0.29
-
 vincoside pH 5.0, 30°C Carapichea ipecacuanha
3.2.1.21 0.32
-
 N-deacetylipecoside pH 5.0, 30°C Carapichea ipecacuanha
3.2.1.21 0.39
-
 6-O-methyl-N-deacetylipecoside pH 5.0, 30°C Carapichea ipecacuanha

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
3.2.1.B16 cytosol
-
 Carapichea ipecacuanha 5829
-

Molecular Weight [Da]

EC Number Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
3.2.1.B16 61800
-
 calculated from sequence Carapichea ipecacuanha

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3.2.1.B16 1beta(R)-6-O-methyl-N-deacetylipecoside + H2O Carapichea ipecacuanha the enzyme is involved in alkaloid biosynthesis 1beta(R)-6-O-methyl-N-deacetylipecoside aglycone + D-glucose
-
 ?
3.2.1.B16 1beta(R)-N-deacetylipecoside + H2O Carapichea ipecacuanha 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 aglycone + D-glucose
-
 ?
3.2.1.B16 ipecoside + H2O Carapichea ipecacuanha the enzyme is involved in alkaloid biosynthesis ipecoside aglycone + D-glucose
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
3.2.1.B16 Carapichea ipecacuanha B6ZKM3
-
-
3.2.1.21 Carapichea ipecacuanha B6ZKM3
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
3.2.1.B16 N-terminal His-tagged IpeGlu1 enzyme is purified to homogeneity from the soluble protein fraction by metal chelation chromatography Carapichea ipecacuanha

Source Tissue

EC Number Source Tissue Comment Organism Textmining
3.2.1.B16 root
-
 Carapichea ipecacuanha
-
3.2.1.B16 shoot
-
 Carapichea ipecacuanha
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.2.1.B16 1alpha(S)-6-O-methyl-N-deacetylisoipecoside + H2O kcat/KM is 16.3% of the value for 1beta(R)-N-deacetylipecoside Carapichea ipecacuanha 1alpha(S)-6-O-methyl-N-deacetylisoipecoside aglycone + D-glucose
-
 ?
3.2.1.B16 1alpha(S)-N-deacetylisoipecoside + H2O kcat/KM is 16.9% of the value for 1beta(R)-N-deacetylipecoside Carapichea ipecacuanha 1alpha(S)-N-deacetylisoipecoside aglycone + D-glucose
-
 ?
3.2.1.B16 1beta(R)-6-O-methyl-N-deacetylipecoside + H2O the enzyme is involved in alkaloid biosynthesis Carapichea ipecacuanha 1beta(R)-6-O-methyl-N-deacetylipecoside aglycone + D-glucose
-
 ?
3.2.1.B16 1beta(R)-6-O-methyl-N-deacetylipecoside + H2O kcat/KM is 90.5% of the value for 1beta(R)-N-deacetylipecoside Carapichea ipecacuanha 1beta(R)-6-O-methyl-N-deacetylipecoside aglycone + D-glucose
-
 ?
3.2.1.B16 1beta(R)-N-deacetylipecoside + H2O the 1beta(R)-epimer N-deacetylipecoside is the precursor mainly of ipecoside and alangiside, the alkaloidal glucosides having a beta-configuration Carapichea ipecacuanha 1beta(R)-N-deacetylipecoside aglycone + D-glucose
-
 ?
3.2.1.B16 1beta(R)-N-deacetylipecoside + H2O 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 Carapichea ipecacuanha 1beta(R)-N-deacetylipecoside aglycone + D-glucose 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 ?
3.2.1.B16 ipecoside + H2O the enzyme is involved in alkaloid biosynthesis Carapichea ipecacuanha ipecoside aglycone + D-glucose
-
 ?
3.2.1.B16 ipecoside + H2O kcat/KM is 5.2fold higher than the value for 1beta(R)-N-deacetylipecoside Carapichea ipecacuanha ipecoside aglycone + D-glucose
-
 ?
3.2.1.B16 additional information no activity with raucaffricine. IpeGlu1 does not accept the lactams, demethylisoalangiside and demethylalangiside, as substrate Carapichea ipecacuanha ?
-
 ?
3.2.1.B16 vincoside + H2O kcat/KM is 11.1% of the value for 1beta(R)-N-deacetylipecoside Carapichea ipecacuanha vincoside aglycone + D-glucose
-
 ?
3.2.1.21 6-O-methyl-N-deacetylipecoside + H2O 90.5% of the efficiency with N-deacetylipecoside Carapichea ipecacuanha ?
-
 ?
3.2.1.21 ipecoside + H2O 586% of the efficiency with N-deacetylipecoside Carapichea ipecacuanha ?
-
 ?
3.2.1.21 additional information isoform 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. 6-O-methyl derivatives are hydrolyzed as efficiently as non-methylated substrates. IpeGlu1 lacks stereospecificity for its substrates. 1(R)-epimers are preferred to 1(S)-epimers Carapichea ipecacuanha ?
-
 ?
3.2.1.21 N-deacetylipecoside + H2O
-
 Carapichea ipecacuanha ?
-
 ?
3.2.1.21 strictosidine + H2O 12.6% of the efficiency with N-deacetylipecoside Carapichea ipecacuanha ?
-
 ?
3.2.1.21 vincoside + H2O 25.1% of the efficiency with N-deacetylipecoside Carapichea ipecacuanha ?
-
 ?

Subunits

EC Number Subunits Comment Organism
3.2.1.B16 ? x * 61800, calculated from sequence Carapichea ipecacuanha

Synonyms

EC Number Synonyms Comment Organism
3.2.1.B16 Ipecac alkaloid beta-D-glucosidase
-
 Carapichea ipecacuanha
3.2.1.B16 IpeGlu1
-
 Carapichea ipecacuanha
3.2.1.21 Glu1
-
 Carapichea ipecacuanha

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
3.2.1.B16 30
-
 assay at Carapichea ipecacuanha
3.2.1.B16 55 60
-
 Carapichea ipecacuanha

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
3.2.1.B16 6.4
-
 vincoside pH 5.0, 30°C Carapichea ipecacuanha
3.2.1.B16 18.7
-
 1alpha(S)-6-O-methyl-N-deacetylisoipecoside pH 5.0, 30°C Carapichea ipecacuanha
3.2.1.B16 28.2
-
 1beta(R)-N-deacetylipecoside pH 5.0, 30°C Carapichea ipecacuanha
3.2.1.B16 31.1
-
 1beta(R)-6-O-methyl-N-deacetylipecoside pH 5.0, 30°C Carapichea ipecacuanha
3.2.1.B16 51.6
-
 ipecoside pH 5.0, 30°C Carapichea ipecacuanha
3.2.1.B16 86.3
-
 1alpha(S)-N-deacetylisoipecoside pH 5.0, 30°C Carapichea ipecacuanha
3.2.1.21 2.1
-
 strictosidine pH 5.0, 30°C Carapichea ipecacuanha
3.2.1.21 6.4
-
 vincoside pH 5.0, 30°C Carapichea ipecacuanha
3.2.1.21 28.2
-
 N-deacetylipecoside pH 5.0, 30°C Carapichea ipecacuanha
3.2.1.21 31.1
-
 6-O-methyl-N-deacetylipecoside pH 5.0, 30°C Carapichea ipecacuanha
3.2.1.21 51.6
-
 ipecoside pH 5.0, 30°C Carapichea ipecacuanha

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
3.2.1.B16 5
-
 substrate: 1alpha(S)-N-deacetylisoipecoside or 1beta(R)-N-deacetylipecoside Carapichea ipecacuanha

pI Value

EC Number Organism Comment pI Value Maximum pI Value
3.2.1.B16 Carapichea ipecacuanha calculated from sequence
-
 6.26

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
3.2.1.B16 14.4
-
 1alpha(S)-6-O-methyl-N-deacetylisoipecoside pH 5.0, 30°C Carapichea ipecacuanha
3.2.1.B16 14.9
-
 1alpha(S)-N-deacetylisoipecoside pH 5.0, 30°C Carapichea ipecacuanha
3.2.1.B16 22.1
-
 vincoside pH 5.0, 30°C Carapichea ipecacuanha
3.2.1.B16 79.7
-
 1beta(R)-6-O-methyl-N-deacetylipecoside pH 5.0, 30°C Carapichea ipecacuanha
3.2.1.B16 88.1
-
 1beta(R)-N-deacetylipecoside pH 5.0, 30°C Carapichea ipecacuanha
3.2.1.B16 516
-
 ipecoside pH 5.0, 30°C Carapichea ipecacuanha