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Ligand (S)-norcoclaurine

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (1 result)

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Show Natural Substrate (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.1.1.128

S-adenosyl-L-methionine + (S)-norcoclaurine = S-adenosyl-L-homocysteine + (S)-coclaurine

689501, 676471, 670561

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In Vivo Product in Enzyme-catalyzed Reactions (3 results)

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Show Natural Product (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.2.1.78

4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde = (S)-Norcoclaurine + H2O

, 653569, 652296

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4.2.1.78

4-hydroxyphenylacetaldehyde + 4-(2-aminoethyl)benzene-1,2-diol = (S)-norcoclaurine + H2O

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-

4.2.1.78

4-hydroxyphenylacetaldehyde + dopamine = (S)-norcoclaurine + H2O

-

-

4.2.1.78

3 entries

Substrate in Enzyme-catalyzed Reactions (3 results)

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Show Substrate (3 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.1.1.115

S-Adenosyl-L-methionine + (S)-norcoclaurine = ?

15190

-

2.1.1.128

S-adenosyl-L-methionine + (S)-norcoclaurine = S-adenosyl-L-homocysteine + (S)-coclaurine

676471, 689501, 720882, 756838, 720710, 670561

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2.1.1.140

(S)-norcoclaurine + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + (R)-N-methylnorcoclaurine

15230

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Product in Enzyme-catalyzed Reactions (3 results)

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Show Product (3 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.2.1.78

4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde = (S)-Norcoclaurine + H2O

5895, , 5894, 653569, 652296

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4.2.1.78

4-hydroxyphenylacetaldehyde + 4-(2-aminoethyl)benzene-1,2-diol = (S)-norcoclaurine + H2O

-

-

4.2.1.78

4-hydroxyphenylacetaldehyde + dopamine = (S)-norcoclaurine + H2O

-

-

4.2.1.78

3 entries

Enzyme Kinetic Parameters

K_M Value (1 result)

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Show KM Value (1 entry)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.1.1.140

0.05

-

probably allosteric enzyme, Hill coeffizient 2.6

15230

References & Links

Literature References (12)

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Show Reference (12 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

5894

-

(S)-Norlaudanosoline synthase: the first enzyme in the benzylisoquinoline biosynthetic pathway

1981

Rueffer, M.; El-Shagi, H.; Nagakura, N.; Zenk, M.H.

FEBS Lett.

129

5-9

5895

17404986

Partial purification and properties of (S)-norlaudanosoline synthase from Eschscholtzia tenuifolia cell cultures

1983

Schumacher, H.M.; Rueffer, M.; Nagakura, N.; Zenk, M.H.

J. Med. Plant Res.

48

212-220

15190

-

Purification and characterization of three isoforms of S-adenosyl-L-methionine: (R,S)-tetrahydrobenzylisoquinoline-N-methyltransferase from Berberis koetineana cell cultures

1990

Frenzel, T.; Zenk, M.H.

Phytochemistry

29

3491-3497

15230

-

S-Adenosyl-L-methionine:(S)-coclaurine-N-methyltransferase from Tinospora cordifolia

1995

Loeffler, S.; Deus-Neumann, B.; Zenk, M.H.

Phytochemistry

38

1387-1395

652296

12107162

Purification and characterization of norcoclaurine synthase. The first committed enzyme in benzylisoquinoline alkaloid biosynthesis in plants

2002

Samanani, N.; Facchini, P.J.

J. Biol. Chem.

277

33878-33883

653569

11722126

Isolation and partial characterization of norcoclaurine synthase, the first committed step in benzylisoquinoline alkaloid biosynthesis, from opium poppy

2001

Samanani, N.; Facchini, P.J.

Planta

213

898-906

670561

16813579

The role of phloem sieve elements and laticifers in the biosynthesis and accumulation of alkaloids in opium poppy

2006

Samanani, N.; Alcantara, J.; Bourgault, R.; Zulak, K.G.; Facchini, P.J.

Plant J.

47

547-563

676471

17189286

Overexpression of Coptis japonica norcoclaurine 6-O-methyltransferase overcomes the rate-limiting step in Benzylisoquinoline alkaloid biosynthesis in cultured Eschscholzia californica

2007

Inui, T.; Tamura, K.; Fujii, N.; Morishige, T.; Sato, F.

Plant Cell Physiol.

48

252-262

689501

17132631

Identification of a WRKY protein as a transcriptional regulator of benzylisoquinoline alkaloid biosynthesis in Coptis japonica

2007

Kato, N.; Dubouzet, E.; Kokabu, Y.; Yoshida, S.; Taniguchi, Y.; Dubouzet, J.G.; Yazaki, K.; Sato, F.

Plant Cell Physiol.

48

8-18

720710

22725256

Systematic silencing of benzylisoquinoline alkaloid biosynthetic genes reveals the major route to papaverine in opium poppy

2012

Desgagne-Penix, I.; Facchini, P.

Plant J.

72

331-344

720882

20689233

Molecular characterization of O-methyltransferases involved in isoquinoline alkaloid biosynthesis in Coptis japonica

2010

Morishige, T.; Tamakoshi, M.; Takemura, T.; Sato, F.

Proc. Jpn. Acad. Ser. B

86

757-768

756838

29915609

Identification and characterization of genes involved in benzylisoquinoline alkaloid biosynthesis in coptis species

2018

He, S.; Liang, Y.; Cong, K.; Chen, G.; Zhao, X.; Zhao, Q.; Zhang, J.; Wang, X.; Dong, Y.; Yang, J.; Zhang, G.; Qian, Z.; Fan, W.; Yang, S.

Front. Plant Sci.

9

731

Links to other databases for (S)-norcoclaurine

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Show Links (1 entry)

ChEBI

PubChem

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