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Literature summary extracted from

  • Kilgore, M.B.; Augustin, M.M.; May, G.D.; Crow, J.A.; Kutchan, T.M.
    CYP96T1 of Narcissus sp. aff. pseudonarcissus catalyzes formation of the para-para' C-C phenol couple in the Amaryllidaceae alkaloids (2016), Front. Plant Sci., 7, 225.
    View publication on PubMedView publication on EuropePMC

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.14.19.50 4'-O-methyl-N-methylnorbelladine substrate inhibition Narcissus aff. pseudonarcissus MK-2014
1.14.19.50 4'-O-methylnorbelladine substrate inhibition Narcissus aff. pseudonarcissus MK-2014

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.14.19.50 0.00113
-
 4'-O-methylnorbelladine pH 8.0, 30°C Narcissus aff. pseudonarcissus MK-2014
1.14.19.50 0.00328
-
 4'-O-methyl-N-methylnorbelladine pH 8.0, 30°C Narcissus aff. pseudonarcissus MK-2014
1.14.19.50 0.637
-
 (S)-Coclaurine pH 8.0, 30°C Narcissus aff. pseudonarcissus MK-2014
1.14.19.50 0.659
-
 (R)-coclaurine pH 8.0, 30°C Narcissus aff. pseudonarcissus MK-2014

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.1.1.336 S-adenosyl-L-methionine + norbelladine Narcissus aff. pseudonarcissus MK-2014
-
 S-adenosyl-L-homocysteine + 4'-O-methylnorbelladine
-
 ?
2.1.1.336 S-adenosyl-L-methionine + norbelladine Galanthus elwesii
-
 S-adenosyl-L-homocysteine + 4'-O-methylnorbelladine
-
 ?
2.1.1.336 S-adenosyl-L-methionine + norbelladine Galanthus sp.
-
 S-adenosyl-L-homocysteine + 4'-O-methylnorbelladine
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.14.19.50 Narcissus aff. pseudonarcissus MK-2014 A0A140IL90
-
-
2.1.1.336 Galanthus elwesii
-
-
-
2.1.1.336 Galanthus sp.
-
-
-
2.1.1.336 Narcissus aff. pseudonarcissus MK-2014 A0A077EWA5
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
2.1.1.336 bulb
-
 Narcissus aff. pseudonarcissus MK-2014
-
2.1.1.336 bulb
-
 Galanthus elwesii
-
2.1.1.336 bulb
-
 Galanthus sp.
-
2.1.1.336 inflorescence
-
 Narcissus aff. pseudonarcissus MK-2014
-
2.1.1.336 inflorescence
-
 Galanthus elwesii
-
2.1.1.336 inflorescence
-
 Galanthus sp.
-
2.1.1.336 leaf
-
 Narcissus aff. pseudonarcissus MK-2014
-
2.1.1.336 leaf
-
 Galanthus elwesii
-
2.1.1.336 leaf
-
 Galanthus sp.
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.19.50 (R)-coclaurine + [reduced NADPH-hemoprotein reductase] + O2
-
 Narcissus aff. pseudonarcissus MK-2014 ? + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
 ?
1.14.19.50 (S)-coclaurine + [reduced NADPH-hemoprotein reductase] + O2
-
 Narcissus aff. pseudonarcissus MK-2014 ? + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
 ?
1.14.19.50 4'-O-methyl-N-methylnorbelladine + [reduced NADPH-hemoprotein reductase] + O2
-
 Narcissus aff. pseudonarcissus MK-2014 ? + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
 ?
1.14.19.50 4'-O-methylnorbelladine + [reduced NADPH-hemoprotein reductase] + O2
-
 Narcissus aff. pseudonarcissus MK-2014 (4aS,10bR)-noroxomaritidine + [oxidized NADPH-hemoprotein reductase] + 2 H2O formation of the para-ortho' phenol coupled product, N-demethylnarwedine, at less than 1% of the total product ?
1.14.19.50 4'-O-methylnorbelladine + [reduced NADPH-hemoprotein reductase] + O2
-
 Narcissus aff. pseudonarcissus MK-2014 (4aR,10bS)-noroxomaritidine + [oxidized NADPH-hemoprotein reductase] + 2 H2O formation of the para-ortho' phenol coupled product, N-demethylnarwedine, at less than 1% of the total product ?
1.14.19.50 additional information the enzyme catalyzes a C-C phenol-coupling reaction with para-para’ regiospecificity. No substrates: norbelladine, N-methylnorbelladine, 3'-O-methylnorbelladine, 3',4'-O-dimethylnorbelladine Narcissus aff. pseudonarcissus MK-2014 ?
-
 ?
2.1.1.336 S-adenosyl-L-methionine + norbelladine
-
 Narcissus aff. pseudonarcissus MK-2014 S-adenosyl-L-homocysteine + 4'-O-methylnorbelladine
-
 ?
2.1.1.336 S-adenosyl-L-methionine + norbelladine
-
 Galanthus elwesii S-adenosyl-L-homocysteine + 4'-O-methylnorbelladine
-
 ?
2.1.1.336 S-adenosyl-L-methionine + norbelladine
-
 Galanthus sp. S-adenosyl-L-homocysteine + 4'-O-methylnorbelladine
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.14.19.50 CYP96T1
-
 Narcissus aff. pseudonarcissus MK-2014
2.1.1.336 N4OMT1
-
 Narcissus aff. pseudonarcissus MK-2014
2.1.1.336 N4OMT1
-
 Galanthus elwesii
2.1.1.336 N4OMT1
-
 Galanthus sp.

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
1.14.19.50 0.022
-
 (S)-Coclaurine pH 8.0, 30°C Narcissus aff. pseudonarcissus MK-2014
1.14.19.50 0.035
-
 (R)-coclaurine pH 8.0, 30°C Narcissus aff. pseudonarcissus MK-2014
1.14.19.50 0.041
-
 4'-O-methyl-N-methylnorbelladine pH 8.0, 30°C Narcissus aff. pseudonarcissus MK-2014
1.14.19.50 0.25
-
 4'-O-methylnorbelladine pH 8.0, 30°C Narcissus aff. pseudonarcissus MK-2014

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
1.14.19.50 0.064
-
 4'-O-methylnorbelladine pH 8.0, 30°C Narcissus aff. pseudonarcissus MK-2014
1.14.19.50 0.174
-
 4'-O-methyl-N-methylnorbelladine pH 8.0, 30°C Narcissus aff. pseudonarcissus MK-2014

General Information

EC Number General Information Comment Organism
1.14.19.50 physiological function CYP96T1 catalyzes the first major branch in Amaryllidaceae alkaloid biosynthesis Narcissus aff. pseudonarcissus MK-2014

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
1.14.19.50 0.035
-
 (S)-Coclaurine pH 8.0, 30°C Narcissus aff. pseudonarcissus MK-2014
1.14.19.50 0.053
-
 (R)-coclaurine pH 8.0, 30°C Narcissus aff. pseudonarcissus MK-2014
1.14.19.50 12.37
-
 4'-O-methyl-N-methylnorbelladine pH 8.0, 30°C Narcissus aff. pseudonarcissus MK-2014
1.14.19.50 216.7
-
 4'-O-methylnorbelladine pH 8.0, 30°C Narcissus aff. pseudonarcissus MK-2014