Information on EC 4.2.3.165 - (1R,4R,5S)-(-)-guaia-6,10(14)-diene synthase

for references in articles please use BRENDA:EC4.2.3.165

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EC Tree 4 Lyases 4.2 Carbon-oxygen lyases 4.2.3 Acting on phosphates 4.2.3.165 (1R,4R,5S)-(-)-guaia-6,10(14)-diene synthase

IUBMB Comments

The original enzyme (STC5) from the fungus Fusarium fujikuroi is inactive because of a critically naturally occuring mutation that leads to an asparagine to lysine exchange in the NSE (Asn-Ser-Glu) triad, a highly conserved motif of type I terpene cyclases. Sequence correction by site-directed mutagenesis (K288N) restores activity.

The expected taxonomic range for this enzyme is: Fusarium fujikuroi species complex

Reaction Schemes

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(2E,6E)-farnesyl diphosphate

(1R,4R,5S)-(-)-guaia-6,10(14)-diene

diphosphate

Synonyms
STC5, more

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SYNONYM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

STC5

STC5

STC5

Fusarium fujikuroi IMI 58289

S0ENM8

STC5

Fusarium mangiferae

739857

STC5

Fusarium proliferatum

739857

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REACTION

REACTION DIAGRAM

COMMENTARY

ORGANISM

UNIPROT

LITERATURE

(2E,6E)-farnesyl diphosphate = (1R,4R,5S)-(-)-guaia-6,10(14)-diene + diphosphate

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SYSTEMATIC NAME

IUBMB Comments

(2E,6E)-farnesyl-diphosphate diphosphate-lyase [cyclizing, (1R,4R,5S)-(-)-guaia-6,10(14)-diene-forming]

The original enzyme (STC5) from the fungus Fusarium fujikuroi is inactive because of a critically naturally occuring mutation that leads to an asparagine to lysine exchange in the NSE (Asn-Ser-Glu) triad, a highly conserved motif of type I terpene cyclases. Sequence correction by site-directed mutagenesis (K288N) restores activity.

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SUBSTRATE

PRODUCT

REACTION DIAGRAM

ORGANISM

UNIPROT

LITERATURE

COMMENTARY

Reversibility
r=reversible
ir=irreversible
?=not specified

(2E,6E)-farnesyl diphosphate

(1R,4R,5S)-(-)-guaia-6,10(14)-diene + diphosphate

8 entries

(2E,6E)-farnesyl diphosphate

(1R,4R,5S)-(-)-guaia-6,10(14)-diene + diphosphate

Fusarium fujikuroi

S0ENM8

739857

Substrates: -
Products: -

(2E,6E)-farnesyl diphosphate

(1R,4R,5S)-(-)-guaia-6,10(14)-diene + diphosphate

Fusarium fujikuroi

S0ENM8

739857

Substrates: the original STC5 from Fusarium fujikuroi is inactive because of a critically naturally occuring mutation at position 288 in STC5 that leads to an asparagine to lysine exchange in the NSE triad. Sequence correction by site-directed mutagenesis (K288N) restores activity. No activity with geranyl diphosphate and geranylgeranyl diphosphate
Products: (1R,4R,5S)-(-)-guaia-6,10(14)-diene = (1R)-1-methyl-4-methylidene-7-(propan-2-yl)-1,2,3,3a,4,5,6,8a-octahydroazulene i.e. (1R)-7-isopropyl-1-methyl-4-methylene-1,2,3,3a,4,5,6,8a-octahydroazulene

(2E,6E)-farnesyl diphosphate

(1R,4R,5S)-(-)-guaia-6,10(14)-diene + diphosphate

Fusarium fujikuroi IMI 58289

S0ENM8

739857

Substrates: -
Products: -

(2E,6E)-farnesyl diphosphate

(1R,4R,5S)-(-)-guaia-6,10(14)-diene + diphosphate

Fusarium fujikuroi IMI 58289

S0ENM8

739857

(2E,6E)-farnesyl diphosphate

(1R,4R,5S)-(-)-guaia-6,10(14)-diene + diphosphate

Fusarium mangiferae

739857

Substrates: -
Products: -

(2E,6E)-farnesyl diphosphate

(1R,4R,5S)-(-)-guaia-6,10(14)-diene + diphosphate

Fusarium mangiferae

739857

Substrates: no activity with geranyl diphosphate and geranylgeranyl diphosphate
Products: (1R,4R,5S)-(-)-guaia-6,10(14)-diene i.e. (1R)-1-methyl-4-methylidene-7-(propan-2-yl)-1,2,3,3a,4,5,6,8a-octahydroazulene i.e. (1R)-7-isopropyl-1-methyl-4-methylene-1,2,3,3a,4,5,6,8a-octahydroazulene

(2E,6E)-farnesyl diphosphate

(1R,4R,5S)-(-)-guaia-6,10(14)-diene + diphosphate

Fusarium proliferatum

739857

Substrates: -
Products: -

(2E,6E)-farnesyl diphosphate

(1R,4R,5S)-(-)-guaia-6,10(14)-diene + diphosphate

Fusarium proliferatum

739857

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NATURAL SUBSTRATE

NATURAL PRODUCT

REACTION DIAGRAM

ORGANISM

UNIPROT

LITERATURE

COMMENTARY

REVERSIBILITY
r=reversible
ir=irreversible
?=not specified

(2E,6E)-farnesyl diphosphate

(1R,4R,5S)-(-)-guaia-6,10(14)-diene + diphosphate

4 entries

(2E,6E)-farnesyl diphosphate

(1R,4R,5S)-(-)-guaia-6,10(14)-diene + diphosphate

Fusarium fujikuroi

S0ENM8

739857

Substrates: -
Products: -

(2E,6E)-farnesyl diphosphate

(1R,4R,5S)-(-)-guaia-6,10(14)-diene + diphosphate

Fusarium fujikuroi IMI 58289

S0ENM8

739857

Substrates: -
Products: -

(2E,6E)-farnesyl diphosphate

(1R,4R,5S)-(-)-guaia-6,10(14)-diene + diphosphate

Fusarium mangiferae

739857

Substrates: -
Products: -

(2E,6E)-farnesyl diphosphate

(1R,4R,5S)-(-)-guaia-6,10(14)-diene + diphosphate

Fusarium proliferatum

739857

Substrates: -
Products: -

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TEMPERATURE OPTIMUM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

assay

assay

Fusarium proliferatum

assay

739857

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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

Fusarium fujikuroi

the original STC5 from Fusarium fujikuroi is inactive because of a critically naturally occuring mutation at position 288 in STC5 that leads to an asparagine to lysine exchange in the NSE triad. Sequence correction by site-directed mutagenesis (K288N) restores activity

739857

S0ENM8

UniProt

brenda

Fusarium fujikuroi IMI 58289

739857

S0ENM8

UniProt

brenda

Fusarium mangiferae

739857

brenda

Fusarium proliferatum

739857

brenda

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Highest Expressing Human Cell Lines

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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).

A0A1L7VZE7 pBLAST

GUDIS_FUSPR

Fusarium proliferatum (strain ET1)

401

45857

Swiss-Prot

Show Sequence

A0A1L7U8F2 pBLAST

GUDIS_FUSMA

Fusarium mangiferae

401

45843

Swiss-Prot

Show Sequence

S0ENM8 pBLAST

GUDIS_GIBF5

Gibberella fujikuroi (strain CBS 195.34 / IMI 58289 / NRRL A-6831)

401

45986

Swiss-Prot

Show Sequence

other Location (Reliability: 2)

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PROTEIN VARIANTS

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

K288N

K288N

K288N

Fusarium fujikuroi IMI 58289

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PURIFICATION (Commentary)

ORGANISM

UNIPROT

LITERATURE

Fusarium proliferatum

739857

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CLONED (Commentary)

ORGANISM

UNIPROT

LITERATURE

overexpression in Escherichia coli

3 entries

overexpression in Escherichia coli

Fusarium fujikuroi

S0ENM8

739857

overexpression in Escherichia coli

Fusarium mangiferae

739857

overexpression in Escherichia coli

Fusarium proliferatum

739857

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REF.

AUTHORS

TITLE

JOURNAL

VOL.

PAGES

YEAR

ORGANISM (UNIPROT)

PUBMED ID

SOURCE

739857

Burkhardt, I.; Siemon, T.; Henrot, M.; Studt, L.; Rosler, S.; Tudzynski, B.; Christmann, M.; Dickschat, J.S.

Mechanistic Characterisation of two sesquiterpene cyclases from the plant pathogenic fungus Fusarium fujikuroi

Angew. Chem. Int. Ed. Engl.

8748-8751

2016

Fusarium fujikuroi (S0ENM8), Fusarium fujikuroi IMI 58289 (S0ENM8), Fusarium mangiferae, Fusarium proliferatum

27294564

brenda

Entries 1 - 20 of 1

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EXTERNAL LINKS (specific for EC-Number 4.2.3.165)

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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