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Literature summary for 2.5.1.109 extracted from

  • Wunsch, C.; Zou, H.X.; Linne, U.; Li, S.M.
    C7-prenylation of tryptophanyl and O-prenylation of tyrosyl residues in dipeptides by an Aspergillus terreus prenyltransferase (2015), Appl. Microbiol. Biotechnol., 99, 1719-1730.
    View publication on PubMed

Application

Application Comment Organism
synthesis regularly C7-prenylated cyclic dipeptides are successfully obtained by using the member of the DMATS family, CdpC7PT from Aspergillus terreus Aspergillus terreus

Cloned(Commentary)

Cloned (Comment) Organism
gene ATEG_04218 or cdpC7PT, cloning from genomic DNA, DNA and amino acid sequence determination and analysis, recombinant expression of His6-tagged enzyme in Escherichia coli strain M15 Aspergillus terreus

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
additional information
-
additional information Michaelis-Menten kinetics, for the tryptophan-containing cyclic dipeptides, KM values between 0.239 and 0.747 mM and turnover numbers in the range of 0.009-0.049/s are determined Aspergillus terreus
0.0785
-
dimethylallyl diphosphate pH 7.5, 37°C Aspergillus terreus
0.204
-
(S)-benzodiazepinedione pH 7.5, 37°C Aspergillus terreus
1.411
-
cyclo-L-Tyr-L-Tyr pH 7.5, 37°C Aspergillus terreus

Metals/Ions

Metals/Ions Comment Organism Structure
Ca2+ activates 58% at 5 mM Aspergillus terreus
Mg2+ activates 20% at 5 mM Aspergillus terreus
Mn2+ activates 31% at 5 mM Aspergillus terreus
additional information no significant effect by 5 mM EDTA. The enzyme reaction of CdpC7PT is independent of metal ions, but can be enhanced by Ca2+, Mn2+, and Mg2+ Aspergillus terreus

Molecular Weight [Da]

Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
62000
-
recombinant His6-tagged enzyme, gel filtration Aspergillus terreus

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
dimethylallyl diphosphate + cyclo-L-Trp-L-Trp Aspergillus terreus attachment of the prenyl moiety to C-7 of the indole ring diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Trp
-
?
dimethylallyl diphosphate + cyclo-L-Trp-Xaa Aspergillus oryzae
-
diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-Xaa
-
?
additional information Aspergillus terreus for some substrates, reversely C3- or N1-prenylated derivatives are identified as minor products ?
-
?
additional information Aspergillus terreus DSM 1958 for some substrates, reversely C3- or N1-prenylated derivatives are identified as minor products ?
-
?

Organism

Organism UniProt Comment Textmining
Aspergillus oryzae
-
gene cdpC7PT
-
Aspergillus terreus Q0CQ16 gene ATEG_04218 or cdpC7PT
-
Aspergillus terreus DSM 1958 Q0CQ16 gene ATEG_04218 or cdpC7PT
-

Purification (Commentary)

Purification (Comment) Organism
recombinant His6-tagged enzyme from Escherichia coli strain M15 by nickel affinity chromatography Aspergillus terreus

Source Tissue

Source Tissue Comment Organism Textmining
mycelium
-
Aspergillus oryzae
-
mycelium
-
Aspergillus terreus
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
dimethylallyl diphosphate + (R)-benzodiazepinedione low activity, (R)-benzodiazepinedione consists of a tryptophanyl and an anthranilyl moiety Aspergillus terreus diphosphate + ?
-
?
dimethylallyl diphosphate + (S)-benzodiazepinedione best substrate, (S)-benzodiazepinedione consists of a tryptophanyl and an anthranilyl moiety Aspergillus terreus diphosphate + ?
-
?
dimethylallyl diphosphate + benzodiazepinedione best substrate, active only with benzodiazepinedione consisting of a D-tryptophanyl and an anthranilyl moiety, poor activity with the L-Tryp isomer Aspergillus terreus diphosphate + ?
-
?
dimethylallyl diphosphate + cyclo-D-Trp-D-Pro
-
Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-D-Trp-D-Pro
-
?
dimethylallyl diphosphate + cyclo-D-Trp-D-Pro low activity Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-D-Trp-D-Pro
-
?
dimethylallyl diphosphate + cyclo-D-Trp-L-Ala
-
Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-D-Trp-L-Ala
-
?
dimethylallyl diphosphate + cyclo-D-Trp-L-Pro low activity Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-D-Trp-L-Pro
-
?
dimethylallyl diphosphate + cyclo-D-Trp-L-Trp low activity Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-D-Trp-L-Trp
-
?
dimethylallyl diphosphate + cyclo-L-Trp-D-Ala low activity Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-D-Ala
-
?
dimethylallyl diphosphate + cyclo-L-Trp-D-Pro
-
Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-D-Pro
-
?
dimethylallyl diphosphate + cyclo-L-Trp-Gly
-
Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-Gly
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Ala
-
Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Ala
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Leu
-
Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Leu
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Pro
-
Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Pro
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Trp
-
Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Trp
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Trp higher activity Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Trp
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Trp attachment of the prenyl moiety to C-7 of the indole ring Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Trp
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Trp
-
Aspergillus terreus DSM 1958 diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Trp
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Tyr
-
Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Tyr
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Tyr higher activity Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Tyr
-
?
dimethylallyl diphosphate + cyclo-L-Trp-Xaa
-
Aspergillus oryzae diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-Xaa
-
?
dimethylallyl diphosphate + cyclo-L-Tyr-L-Tyr
-
Aspergillus terreus diphosphate + 4-O-(3-methylbut-2-enyl)-cyclo-L-Tyr-L-Tyr
-
?
dimethylallyl diphosphate + cyclo-LTrp-L-Phe
-
Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Phe
-
?
dimethylallyl diphosphate + L-tryptophan reaction of 7-DMATS, EC 2.5.1.80, low activity Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
-
?
dimethylallyl diphosphate + L-tryptophan reaction of 7-DMATS, EC 2.5.1.80, low activity Aspergillus terreus DSM 1958 diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
-
?
additional information for some substrates, reversely C3- or N1-prenylated derivatives are identified as minor products Aspergillus terreus ?
-
?
additional information the enzyme uses cyclic dipeptides containing L-Trp and attaches the prenyl moiety to C-7 of the indole ring, no activity with cyclo-L-Trp-L-Pro, cyclo-L-Trp-D-Pro, cyclo-D-Trp-L-Pro, cyclo-D-Trp-D-Pro, and cyclo-L-Trp-Gly Aspergillus terreus ?
-
?
additional information the enzyme uses cyclic dipeptides containing L-Trp and attaches the prenyl moiety to C-7 of the indole ring. It also accepts cyclo-L-Tyr-L-Tyr as substrate and catalyzes an O-prenylation at the tyrosyl residue of the dipeptide cyclo-L-Trp-L-Tyr. Substrate specificity, overview. Cyclo-L-Tyr-L-Ser, cyclo-L-Tyr-L-Pro, cyclo-L-Tyr-Gly, and L-tyrosine are poor substrates. CdpC7PT shows a high affinity to its prenyl donor dimethylallyl diphosphate Aspergillus terreus ?
-
?
additional information the enzyme uses cyclic dipeptides containing L-Trp and attaches the prenyl moiety to C-7 of the indole ring. The enzyme showsma relatively narrow substrate specificity Aspergillus oryzae ?
-
?
additional information for some substrates, reversely C3- or N1-prenylated derivatives are identified as minor products Aspergillus terreus DSM 1958 ?
-
?
additional information the enzyme uses cyclic dipeptides containing L-Trp and attaches the prenyl moiety to C-7 of the indole ring, no activity with cyclo-L-Trp-L-Pro, cyclo-L-Trp-D-Pro, cyclo-D-Trp-L-Pro, cyclo-D-Trp-D-Pro, and cyclo-L-Trp-Gly Aspergillus terreus DSM 1958 ?
-
?
additional information the enzyme uses cyclic dipeptides containing L-Trp and attaches the prenyl moiety to C-7 of the indole ring. It also accepts cyclo-L-Tyr-L-Tyr as substrate and catalyzes an O-prenylation at the tyrosyl residue of the dipeptide cyclo-L-Trp-L-Tyr. Substrate specificity, overview. Cyclo-L-Tyr-L-Ser, cyclo-L-Tyr-L-Pro, cyclo-L-Tyr-Gly, and L-tyrosine are poor substrates. CdpC7PT shows a high affinity to its prenyl donor dimethylallyl diphosphate Aspergillus terreus DSM 1958 ?
-
?

Synonyms

Synonyms Comment Organism
CdpC7PT
-
Aspergillus oryzae
CdpC7PT
-
Aspergillus terreus
cyclic dipeptide C7-prenyltransferase
-
Aspergillus oryzae
cyclic dipeptide C7-prenyltransferase
-
Aspergillus terreus

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
assay at Aspergillus terreus

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.012
-
cyclo-L-Tyr-L-Tyr pH 7.5, 37°C Aspergillus terreus
0.067
-
dimethylallyl diphosphate pH 7.5, 37°C Aspergillus terreus
0.125
-
(S)-benzodiazepinedione pH 7.5, 37°C Aspergillus terreus

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.5
-
assay at Aspergillus terreus

General Information

General Information Comment Organism
evolution the enzyme belongs to the DMATS superfamily Aspergillus oryzae
evolution the enzyme belongs to the DMATS superfamily Aspergillus terreus