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Literature summary 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

EC Number Application Comment Organism
2.5.1.109 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)

EC Number Cloned (Comment) Organism
2.5.1.109 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]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
2.5.1.109 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
2.5.1.109 0.0785
-
 dimethylallyl diphosphate pH 7.5, 37°C Aspergillus terreus
2.5.1.109 0.204
-
 (S)-benzodiazepinedione pH 7.5, 37°C Aspergillus terreus
2.5.1.109 1.411
-
 cyclo-L-Tyr-L-Tyr pH 7.5, 37°C Aspergillus terreus

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
2.5.1.109 Ca2+ activates 58% at 5 mM Aspergillus terreus
2.5.1.109 Mg2+ activates 20% at 5 mM Aspergillus terreus
2.5.1.109 Mn2+ activates 31% at 5 mM Aspergillus terreus
2.5.1.109 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]

EC Number Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
2.5.1.109 62000
-
 recombinant His6-tagged enzyme, gel filtration Aspergillus terreus

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.5.1.109 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
-
 ?
2.5.1.109 dimethylallyl diphosphate + cyclo-L-Trp-Xaa Aspergillus oryzae
-
 diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-Xaa
-
 ?
2.5.1.109 additional information Aspergillus terreus for some substrates, reversely C3- or N1-prenylated derivatives are identified as minor products ?
-
 ?
2.5.1.109 additional information Aspergillus terreus DSM 1958 for some substrates, reversely C3- or N1-prenylated derivatives are identified as minor products ?
-
 ?

Organism

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

Purification (Commentary)

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

Source Tissue

EC Number Source Tissue Comment Organism Textmining
2.5.1.109 mycelium
-
 Aspergillus oryzae
-
2.5.1.109 mycelium
-
 Aspergillus terreus
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.5.1.109 dimethylallyl diphosphate + (R)-benzodiazepinedione low activity, (R)-benzodiazepinedione consists of a tryptophanyl and an anthranilyl moiety Aspergillus terreus diphosphate + ?
-
 ?
2.5.1.109 dimethylallyl diphosphate + (S)-benzodiazepinedione best substrate, (S)-benzodiazepinedione consists of a tryptophanyl and an anthranilyl moiety Aspergillus terreus diphosphate + ?
-
 ?
2.5.1.109 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 + ?
-
 ?
2.5.1.109 dimethylallyl diphosphate + cyclo-D-Trp-D-Pro
-
 Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-D-Trp-D-Pro
-
 ?
2.5.1.109 dimethylallyl diphosphate + cyclo-D-Trp-D-Pro low activity Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-D-Trp-D-Pro
-
 ?
2.5.1.109 dimethylallyl diphosphate + cyclo-D-Trp-L-Ala
-
 Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-D-Trp-L-Ala
-
 ?
2.5.1.109 dimethylallyl diphosphate + cyclo-D-Trp-L-Pro low activity Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-D-Trp-L-Pro
-
 ?
2.5.1.109 dimethylallyl diphosphate + cyclo-D-Trp-L-Trp low activity Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-D-Trp-L-Trp
-
 ?
2.5.1.109 dimethylallyl diphosphate + cyclo-L-Trp-D-Ala low activity Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-D-Ala
-
 ?
2.5.1.109 dimethylallyl diphosphate + cyclo-L-Trp-D-Pro
-
 Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-D-Pro
-
 ?
2.5.1.109 dimethylallyl diphosphate + cyclo-L-Trp-Gly
-
 Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-Gly
-
 ?
2.5.1.109 dimethylallyl diphosphate + cyclo-L-Trp-L-Ala
-
 Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Ala
-
 ?
2.5.1.109 dimethylallyl diphosphate + cyclo-L-Trp-L-Leu
-
 Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Leu
-
 ?
2.5.1.109 dimethylallyl diphosphate + cyclo-L-Trp-L-Pro
-
 Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Pro
-
 ?
2.5.1.109 dimethylallyl diphosphate + cyclo-L-Trp-L-Trp
-
 Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Trp
-
 ?
2.5.1.109 dimethylallyl diphosphate + cyclo-L-Trp-L-Trp higher activity Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Trp
-
 ?
2.5.1.109 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
-
 ?
2.5.1.109 dimethylallyl diphosphate + cyclo-L-Trp-L-Trp
-
 Aspergillus terreus DSM 1958 diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Trp
-
 ?
2.5.1.109 dimethylallyl diphosphate + cyclo-L-Trp-L-Tyr
-
 Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Tyr
-
 ?
2.5.1.109 dimethylallyl diphosphate + cyclo-L-Trp-L-Tyr higher activity Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Tyr
-
 ?
2.5.1.109 dimethylallyl diphosphate + cyclo-L-Trp-Xaa
-
 Aspergillus oryzae diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-Xaa
-
 ?
2.5.1.109 dimethylallyl diphosphate + cyclo-L-Tyr-L-Tyr
-
 Aspergillus terreus diphosphate + 4-O-(3-methylbut-2-enyl)-cyclo-L-Tyr-L-Tyr
-
 ?
2.5.1.109 dimethylallyl diphosphate + cyclo-LTrp-L-Phe
-
 Aspergillus terreus diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Phe
-
 ?
2.5.1.109 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
-
 ?
2.5.1.109 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
-
 ?
2.5.1.109 additional information for some substrates, reversely C3- or N1-prenylated derivatives are identified as minor products Aspergillus terreus ?
-
 ?
2.5.1.109 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 ?
-
 ?
2.5.1.109 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 ?
-
 ?
2.5.1.109 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 ?
-
 ?
2.5.1.109 additional information for some substrates, reversely C3- or N1-prenylated derivatives are identified as minor products Aspergillus terreus DSM 1958 ?
-
 ?
2.5.1.109 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 ?
-
 ?
2.5.1.109 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

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

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
2.5.1.109 37
-
 assay at Aspergillus terreus

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
2.5.1.109 0.012
-
 cyclo-L-Tyr-L-Tyr pH 7.5, 37°C Aspergillus terreus
2.5.1.109 0.067
-
 dimethylallyl diphosphate pH 7.5, 37°C Aspergillus terreus
2.5.1.109 0.125
-
 (S)-benzodiazepinedione pH 7.5, 37°C Aspergillus terreus

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
2.5.1.109 7.5
-
 assay at Aspergillus terreus

General Information

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