Information on EC 2.1.1.94 - tabersonine 16-O-methyltransferase

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EC Tree 2 Transferases 2.1 Transferring one-carbon groups 2.1.1 Methyltransferases 2.1.1.94 tabersonine 16-O-methyltransferase

IUBMB Comments

Involved in the biosynthesis of vindoline from tabersonine in the Madagascar periwinkle, Catharanthus roseus.

The expected taxonomic range for this enzyme is: Catharanthus roseus

2.1.1.94
catharanthus
roseus
16-hydroxylase
indole
vincristine
epidermis
catharanthine
vinblastine
terpenoid
madagascar
periwinkle
carborundum
abrasion
hairy
o-methylation

Reaction Schemes

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S-adenosyl-L-methionine

16-hydroxytabersonine

S-adenosyl-L-homocysteine

16-methoxytabersonine

Synonyms
16omt, 16-hydroxytabersonine-16-o-methyltransferase, tabersonine 16-o-methyltransferase, 11-o-demethyl-17-o-deacetylvindoline 11-o-methyltransferase, 16-hydroxytabersonine 16-o-methyltransferase, more

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SYNONYM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

11-demethyl-17-deacetylvindoline 11-methyltransferase

11-O-demethyl-17-O-deacetylvindoline 11-O-methyltransferase

11-O-demethyl-17-O-deacetylvindoline O-methyltransferase

16-hydroxytabersonine 16-O-methyltransferase

Catharanthus roseus

B0EXJ8

712866

16-hydroxytabersonine-16-O-methyltransferase

Catharanthus roseus

B0EXJ8

689542

16-hydroxytabersonine-O-methyltransferase

16OMT

689542, 712866, 743812, 756243

methyltransferase, 11-demethyl-17-deacetylvindoline 11-

S-adenosyl-L-methionine:11-O-demethyl-17-O-deacetylvindoline 11-O-methyltransferase

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REACTION

REACTION DIAGRAM

COMMENTARY

ORGANISM

UNIPROT

LITERATURE

S-adenosyl-L-methionine + 16-hydroxytabersonine = S-adenosyl-L-homocysteine + 16-methoxytabersonine

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REACTION TYPE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

methyl group transfer

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Go to Pathway Search

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PATHWAY SOURCE

PATHWAYS

KEGG

Biosynthesis of secondary metabolites, Indole alkaloid biosynthesis

MetaCyc

vindoline, vindorosine and vinblastine biosynthesis

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Go to Systematic Name Search

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SYSTEMATIC NAME

IUBMB Comments

S-adenosyl-L-methionine:16-hydroxytabersonine 16-O-methyltransferase

Involved in the biosynthesis of vindoline from tabersonine in the Madagascar periwinkle, Catharanthus roseus.

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CAS REGISTRY NUMBER

COMMENTARY

100984-95-0

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SUBSTRATE

PRODUCT

REACTION DIAGRAM

ORGANISM

UNIPROT

LITERATURE

COMMENTARY

Reversibility
r=reversible
ir=irreversible
?=not specified

S-adenosyl-L-methionine + 11-O-demethyl-17-O-deacetylvindoline

S-adenosyl-L-homocysteine + 17-O-deacetylvindoline

2 entries

S-adenosyl-L-methionine + 16-hydroxytabersonine

S-adenosyl-L-homocysteine + 16-methoxytabersonine

4 entries

S-adenosyl-L-methionine + 11-O-demethyl-17-O-deacetylvindoline

S-adenosyl-L-homocysteine + 17-O-deacetylvindoline

Catharanthus roseus

485674

Substrates: 11-O-demethylvindoline is not accepted as substrate
Products: -

S-adenosyl-L-methionine + 11-O-demethyl-17-O-deacetylvindoline

S-adenosyl-L-homocysteine + 17-O-deacetylvindoline

Catharanthus roseus

485674

Substrates: involved in biosynthesis of the alkaloid vindoline
Products: -

S-adenosyl-L-methionine + 16-hydroxytabersonine

S-adenosyl-L-homocysteine + 16-methoxytabersonine

Catharanthus roseus

B0EXJ8

712866

Substrates: -
Products: -

S-adenosyl-L-methionine + 16-hydroxytabersonine

S-adenosyl-L-homocysteine + 16-methoxytabersonine

Catharanthus roseus

B0EXJ8

743812, 756243

Substrates: -
Products: -

S-adenosyl-L-methionine + 16-hydroxytabersonine

S-adenosyl-L-homocysteine + 16-methoxytabersonine

Catharanthus roseus

756243

Substrates: -
Products: -

S-adenosyl-L-methionine + 16-hydroxytabersonine

S-adenosyl-L-homocysteine + 16-methoxytabersonine

Catharanthus roseus

B0EXJ8

689542

Substrates: 16OMT is highly specific for its alkaloid substrate 16-hydroxytabersonine
Products: -

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NATURAL SUBSTRATE

NATURAL PRODUCT

REACTION DIAGRAM

ORGANISM

UNIPROT

LITERATURE

COMMENTARY

REVERSIBILITY
r=reversible
ir=irreversible
?=not specified

S-adenosyl-L-methionine + 11-O-demethyl-17-O-deacetylvindoline

S-adenosyl-L-homocysteine + 17-O-deacetylvindoline

Catharanthus roseus

485674

Substrates: involved in biosynthesis of the alkaloid vindoline
Products: -

S-adenosyl-L-methionine + 16-hydroxytabersonine

S-adenosyl-L-homocysteine + 16-methoxytabersonine

2 entries

S-adenosyl-L-methionine + 16-hydroxytabersonine

S-adenosyl-L-homocysteine + 16-methoxytabersonine

Catharanthus roseus

B0EXJ8

743812, 756243

Substrates: -
Products: -

S-adenosyl-L-methionine + 16-hydroxytabersonine

S-adenosyl-L-homocysteine + 16-methoxytabersonine

Catharanthus roseus

756243

Substrates: -
Products: -

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INHIBITOR

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

S-adenosyl-L-homocysteine

product inhibition

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KM VALUE [mM]

SUBSTRATE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

0.0026

16-hydroxytabersonine

Catharanthus roseus

B0EXJ8

689542

0.0217

S-adenosyl-L-methionine

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Ki VALUE [mM]

INHIBITOR

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

0.006

S-adenosyl-L-homocysteine

product inhibition

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SPECIFIC ACTIVITY [µmol/min/mg]

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

0.000417

Catharanthus roseus

B0EXJ8

16-hydroxytabersonine as a substrate

689542

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pH OPTIMUM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

7.5

assay at

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pH RANGE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

7 - 7.5

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TEMPERATURE OPTIMUM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

assay at

assay at

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only manually annotated data include textmining data from AMENDAenzyme occurrence in organism, localization and source tissue with reliability ranks include all textmining data from AMENDAenzyme occurrence in organism, localization and source tissue with reliability ranks + FRENDAco-occurrence of enzyme names and organism names (less precise)

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ORGANISM

COMMENTARY

LITERATURE

UNIPROT

SEQUENCE DB

SOURCE

brenda

689542, 712866, 743812, 756243

B0EXJ8

UniProt

brenda

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only manually annotated data include textmining data from AMENDAenzyme occurrence in organism, localization and source tissue with reliability ranks

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SOURCE TISSUE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

SOURCE

cell suspension culture

brenda

brenda

specifically located in the epidermis of aerial organs

brenda

brenda

brenda

predominatly expressed in leaf epidermis

689542

brenda

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only manually annotated data include textmining data from AMENDAenzyme occurrence in organism, localization and source tissue with reliability ranks

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LOCALIZATION

ORGANISM

UNIPROT

COMMENTARY

GeneOntology No.

LITERATURE

SOURCE

brenda

brenda

Highest Expressing Human Cell Lines

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Cell Line Links

Gene Links

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UNIPROT

ENTRY NAME

ORGANISM

NO. OF AA

NO. OF TRANSM. HELICES

MOLECULAR WEIGHT[Da]

SOURCE

SEQUENCE

LOCALIZATION PREDICTION

The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).

B0EXJ8 pBLAST

HTOMT_CATRO

Catharanthus roseus

355

39863

Swiss-Prot

Show Sequence

other Location (Reliability: 3)

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MOLECULAR WEIGHT

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

40000

SDS-PAGE

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SUBUNIT

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

homodimer

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PURIFICATION (Commentary)

ORGANISM

UNIPROT

LITERATURE

using PD-10 column chromatography, Sephadex G150 column chromatography, adenosine-agarose affinity resin and Mono Q anion exchange column chromatography

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CLONED (Commentary)

ORGANISM

UNIPROT

LITERATURE

Catharanthus roseus

B0EXJ8

712866

16-hydroxytabersonine-16-O-methyltransferase is isolated and cloned as a His-tagged fusion protein in Escherichia coli

Catharanthus roseus

B0EXJ8

689542

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REF.

AUTHORS

TITLE

JOURNAL

VOL.

PAGES

YEAR

ORGANISM (UNIPROT)

PUBMED ID

SOURCE

485674

Fahn, W.; Laussermair, E.; Deus-Neumann, B.; St�ckigt, J.

Late enzymes of vindoline biosynthesis. S-adenosyl-L-methionine:11-O-demethyl-17-O-deacetylvindoline 11-O-methyltransferase and unspecific acetylesterase

Plant Cell Rep.

337-340

1985

Catharanthus roseus

24254077

brenda

689542

Levac, D.; Murata, J.; Kim, W.S.; De Luca, V.

Application of carborundum abrasion for investigating the leaf epidermis: molecular cloning of Catharanthus roseus 16-hydroxytabersonine-16-O-methyltransferase

Plant J.

225-236

2008

Catharanthus roseus (B0EXJ8), Catharanthus roseus

18053006

brenda

712866

Guirimand, G.; Guihur, A.; Poutrain, P.; Hericourt, F.; Mahroug, S.; St-Pierre, B.; Burlat, V.; Courdavault, V.

Spatial organization of the vindoline biosynthetic pathway in Catharanthus roseus

J. Plant Physiol.

168

549-557

2010

Catharanthus roseus (B0EXJ8), Catharanthus roseus

21047699

brenda

743812

Pandey, S.S.; Singh, S.; Babu, C.S.; Shanker, K.; Srivastava, N.K.; Shukla, A.K.; Kalra, A.

Fungal endophytes of Catharanthus roseus enhance vindoline content by modulating structural and regulatory genes related to terpenoid indole alkaloid biosynthesis

Sci. Rep.

26583

2016

Catharanthus roseus (B0EXJ8)

27220774

brenda

756243

Sun, J.; Zhao, L.; Shao, Z.; Shanks, J.; Peebles, C.A.M.

Expression of tabersonine 16-hydroxylase and 16-hydroxytabersonine-O-methyltransferase in Catharanthus roseus hairy roots

Biotechnol. Bioeng.

115

673-683

2018

Catharanthus roseus (B0EXJ8), Catharanthus roseus

29105731

brenda

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EXTERNAL LINKS (specific for EC-Number 2.1.1.94)

ExplorEnz (official portal for IUBMB Enzyme Nomenclature)

Expasy Enzyme Nomenclature Database

KEGG

SABIO-RK

NCBI: PubMed, Protein, Nucleotide, Structure, Gene, OMIM

Enzyme Nomenclature (alternative site)

UniProt

PDB

PROSITE Database of protein families and domains

InterPro (database of protein families, domains and functional sites)

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