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Literature summary for 4.2.99.22 extracted from

  • Nomura, T.; Ogita, S.; Kato, Y.
    One-step enzymatic synthesis of 1-tuliposide a using tuliposide-converting enzyme (2018), Appl. Biochem. Biotechnol., 188, 12-28.
    View publication on PubMed

Cloned(Commentary)

Cloned (Comment) Organism
gene TgTCEA1, recombinant expression of the wild-type enzyme in Escherichia coli BL21-CodonPlus (DE3)-RIL/pET28a Tulipa gesneriana

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
additional information
-
additional information Michaelis-Menten kinetics Tulipa gesneriana
2
-
1,6-tuliposide D recombinant enzyme, pH 6.5, 22°C Tulipa gesneriana
3.2
-
tuliposide F recombinant enzyme, pH 6.5, 22°C Tulipa gesneriana
11
-
6-tuliposide A recombinant enzyme, pH 6.5, 22°C Tulipa gesneriana
44
-
6-tuliposide B recombinant enzyme, pH 6.5, 22°C Tulipa gesneriana

Localization

Localization Comment Organism GeneOntology No. Textmining
chloroplast
-
Tulipa gesneriana 9507
-

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1,6-tuliposide D Tulipa gesneriana
-
tulipalin A + 1-tuliposide A
-
?
6-tuliposide A Tulipa gesneriana
-
tulipalin A + D-glucose
-
?

Organism

Organism UniProt Comment Textmining
Tulipa gesneriana I4DST8 cv. White Memories
-

Purification (Commentary)

Purification (Comment) Organism
recombinant wild-type enzyme from Escherichia coli BL21-CodonPlus (DE3)-RIL/pET28a Tulipa gesneriana

Source Tissue

Source Tissue Comment Organism Textmining
bulb
-
Tulipa gesneriana
-
flower
-
Tulipa gesneriana
-
petal
-
Tulipa gesneriana
-

Specific Activity [micromol/min/mg]

Specific Activity Minimum [µmol/min/mg] Specific Activity Maximum [µmol/min/mg] Comment Organism
79
-
recombinant enzyme, substrate 6-PosB, pH 6.5, 22°C Tulipa gesneriana
930
-
recombinant enzyme, substrate PosF, pH 6.5, 22°C Tulipa gesneriana
1700
-
recombinant enzyme, substrate 6-PosA, pH 6.5, 22°C Tulipa gesneriana
4300
-
recombinant enzyme, substrate PosD, pH 6.5, 22°C Tulipa gesneriana

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1,6-tuliposide D
-
Tulipa gesneriana tulipalin A + 1-tuliposide A
-
?
1,6-tuliposide D i.e. PosD, the enzyme catalyzes intramolecular transesterification, PosD is a 1,6-diacyl-glucose type of Pos, the enzyme shows 250% activity with PosD compared to 6-PosA, best substrate Tulipa gesneriana tulipalin A + 1-tuliposide A
-
?
6-tuliposide A
-
Tulipa gesneriana tulipalin A + D-glucose
-
?
6-tuliposide A i.e. 6-PosA, a monoacyl-glucose type of Pos, the enzyme catalyzes intramolecular transesterification, high activity Tulipa gesneriana tulipalin A + D-glucose
-
?
6-tuliposide B i.e. 6-PosB, a monoacyl-glucose type of Pos, the enzyme catalyzes intramolecular transesterification, the enzyme shows 4.6% activity with 6-PosB compared to 6-PosA Tulipa gesneriana tulipalin B + D-glucose
-
?
additional information 6-tuliposide A (6-PosA) is chemically labile, and they can be spontaneously converted to PaA in neutral to weakly basic conditions in vitro. 1-Tuliposide A (1-PosA) is no substrate Tulipa gesneriana ?
-
?
tuliposide F i.e. PosF, the enzyme catalyzes intramolecular transesterification, PosF is a 1,6-diacyl-glucose type of Pos, the enzyme shows 55% activity with PosF compared to 6-PosA, the configuration at the C-3' position of the substrate PosF is S-form Tulipa gesneriana (3R)-3-hydroxy-2-methylidenecyclopentan-1-one + 1-tuliposide A
-
?

Subunits

Subunits Comment Organism
homodimer
-
Tulipa gesneriana

Synonyms

Synonyms Comment Organism
Pos-converting enzyme
-
Tulipa gesneriana
PosA-converting enzyme
-
Tulipa gesneriana
TCEA
-
Tulipa gesneriana
TgTCEA1
-
Tulipa gesneriana
tuliposide A converting enzyme
-
Tulipa gesneriana
tuliposide-converting enzyme
-
Tulipa gesneriana

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
22
-
assay at room temperature Tulipa gesneriana

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
480
-
6-tuliposide B recombinant enzyme, pH 6.5, 22°C Tulipa gesneriana
780
-
tuliposide F recombinant enzyme, pH 6.5, 22°C Tulipa gesneriana
3300
-
1,6-tuliposide D recombinant enzyme, pH 6.5, 22°C Tulipa gesneriana
3900
-
6-tuliposide A recombinant enzyme, pH 6.5, 22°C Tulipa gesneriana

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
6.5
-
assay at Tulipa gesneriana

General Information

General Information Comment Organism
physiological function tuliposide A converting enzyme (TCEA) and tuliposide B-converting enzyme (TCEB) catalyze intramolecular transesterification of 6-PosA and 6-PosB to form the corresponding lactones, PaA and PaB, respectively, and D-glucose. 6-PosA and 6-PosB serve as precursors of the corresponding alpha-methylene-gamma-butyrolactones, tulipalins A (PaA) and B (PaB), respectively, which are formed from the acyl group at the C-6 position. The 1alpha- and 1beta-anomers exist for 6-PosA/6-PosB and both anomers serve as substrates for TCEs. TCEA and TCEB catalyze the formation of PaA/1-PosA and PaB/1-PosA from PosD and PosF, respectively, by acting on the 6-acyl group of PosD and PosF. Neither enzyme acts on the 1-acyl group of PosD, PosF, or 1-PosA. Although intact tulip tissues constitutively accumulate large amounts of 6-Pos, biologically active PaA and PaB are far less abundant and are sometimes barely detectable, PaA and PaB are hardly detectable in intact plants. PaA and PaB respectively show antifungal and antibacterial activities, they are considered to be key secondary metabolites in the chemical defense of tulip, while 6-PosA and 6-PosB are considered to be storage forms of PaA and PaB, respectively. Enzyme TCEB shows lower overall activity than enzyme TCEA Tulipa gesneriana

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
11
-
6-tuliposide B recombinant enzyme, pH 6.5, 22°C Tulipa gesneriana
240
-
tuliposide F recombinant enzyme, pH 6.5, 22°C Tulipa gesneriana
350
-
6-tuliposide A recombinant enzyme, pH 6.5, 22°C Tulipa gesneriana
1700
-
1,6-tuliposide D recombinant enzyme, pH 6.5, 22°C Tulipa gesneriana