BRENDA - Enzyme Database
show all sequences of 4.2.1.78

Enzyme catalysed Pictet-Spengler formation of chiral 1,1-disubstituted- and spiro-tetrahydroisoquinolines

Lichman, B.R.; Zhao, J.; Hailes, H.C.; Ward, J.M.; Nat. Commun. 8, 14883 (2017)

Data extracted from this reference:

Application
Application
Commentary
Organism
synthesis
the enzyme can catalyse the Pictet-Spengler reaction between dopamine and unactivated ketones, thus facilitating the facile biocatalytic generation of 1,1'-disubstituted tetrahydroisoquinolines. Variants of the enzyme showing improved conversions are identified and used to synthesize novel chiral 1,10-disubstituted and spiro-tetrahydroisoquinolines
Thalictrum flavum
Engineering
Protein Variants
Commentary
Organism
A79F
improved turnover of ketones, increase in side-chain steric interactions
Thalictrum flavum
A79I
improved turnover of ketones, increase in side-chain steric interactions
Thalictrum flavum
Organism
Organism
UniProt
Commentary
Textmining
Thalictrum flavum
Q67A25
-
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
Substrate Product ID
4-hydroxyphenylacetone + dopamine
-
748745
Thalictrum flavum
1-(4-hydroxybenzyl)-1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol
-
-
-
?
Synonyms
Synonyms
Commentary
Organism
TfNCS
-
Thalictrum flavum
Application (protein specific)
Application
Commentary
Organism
synthesis
the enzyme can catalyse the Pictet-Spengler reaction between dopamine and unactivated ketones, thus facilitating the facile biocatalytic generation of 1,1'-disubstituted tetrahydroisoquinolines. Variants of the enzyme showing improved conversions are identified and used to synthesize novel chiral 1,10-disubstituted and spiro-tetrahydroisoquinolines
Thalictrum flavum
Engineering (protein specific)
Protein Variants
Commentary
Organism
A79F
improved turnover of ketones, increase in side-chain steric interactions
Thalictrum flavum
A79I
improved turnover of ketones, increase in side-chain steric interactions
Thalictrum flavum
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
ID
4-hydroxyphenylacetone + dopamine
-
748745
Thalictrum flavum
1-(4-hydroxybenzyl)-1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol
-
-
-
?
Other publictions for EC 4.2.1.78
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Synonyms
Temperature Optimum [°C]
Temperature Range [°C]
Temperature Stability [°C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [°C] (protein specific)
Temperature Range [°C] (protein specific)
Temperature Stability [°C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
747372
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3
4
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747130
Lichman
Structural evidence for the d ...
Thalictrum flavum
Biochemistry
56
5274-5277
2017
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748745
Lichman
Enzyme catalysed Pictet-Speng ...
Thalictrum flavum
Nat. Commun.
8
14883
2017
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Vimolmangkang
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4
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4
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Coptis japonica
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1
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1
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4
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1
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1
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1
1
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-
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Thalictrum flavum
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16
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16
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705406
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715141
Bonamore
-
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Thalictrum flavum
Green Chem.
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2010
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1
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1
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1
1
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716518
Lee
Norcoclaurine synthase is a me ...
Coptis japonica, Papaver somniferum, Thalictrum flavum
Plant Cell
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2010
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1
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1
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3
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3
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6
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10
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4
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13
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3
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10
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4
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1
6
6
1
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Thalictrum flavum
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2
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3
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690258
Pasquo
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Thalictrum flavum
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64
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690826
Berkner
Conformation, catalytic site, ...
Thalictrum flavum
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2008
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1
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4
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678219
Luk
Mechanistic studies on norcocl ...
Thalictrum flavum
Biochemistry
46
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2007
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7
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7
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680879
Minami
Functional analysis of norcocl ...
Coptis japonica
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6274-6282
2007
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682682
Berkner
High-yield expression and puri ...
Thalictrum flavum
Protein Expr. Purif.
56
197-204
2007
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1
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1
1
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5
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1
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3
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652296
Samanani
Purification and characterizat ...
Thalictrum flavum ssp. glaucum
J. Biol. Chem.
277
33878-33883
2002
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1
2
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2
1
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1
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2
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1
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1
2
3
1
1
1
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1
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4
-
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-
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653569
Samanani
Isolation and partial characte ...
Eschscholzia californica, no activity in Catharanthus roseus, no activity in Nicotiana tabacum, Papaver somniferum, Thalictrum flavum ssp. glaucum
Planta
213
898-906
2001
2
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1
6
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3
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11
-
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3
-
8
-
2
6
-
6
3
1
1
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3
1
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2
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6
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8
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2
6
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3
1
1
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3
1
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5895
Schumacher
Partial purification and prope ...
Eschscholtzia tenuifolia
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48
212-220
1983
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1
3
1
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1
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1
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1
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1
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2
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2
1
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5894
Rueffer
-
(S)-Norlaudanosoline synthase: ...
Berberis regeliana, Capnoides sempervirens, Eschscholtzia tenuifolia, Eschscholzia pulchella, Fumaria officinalis, Glaucium rubrum, Lamprocapnos spectabilis, Meconopsis cambrica, Papaver somniferum, Ranunculus flammula, Thalictrum minus, Thalictrum tuberosum
FEBS Lett.
129
5-9
1981
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2
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12
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12
-
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12
-
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25
-
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1
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2
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12
-
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12
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25
-
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1
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