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Literature summary for 2.1.1.292 extracted from

  • Huber, T.; Wang, F.; Singh, S.; Johnson, B.; Zhang, J.; Sunkara, M.; Van Lanen, S.; Morris, A.; Phillips, G.; Thorson, J.
    Functional AdoMet isosteres resistant to classical AdoMet degradation pathways (2016), ACS Chem. Biol., 11, 2484-2491 .
    View publication on PubMedView publication on EuropePMC
Search for more literature for 2.1.1.292

Cloned(Commentary)

Cloned (Comment) Organism
gene dnrK, recombinant expression of N-terminally His-tagged enzyme in Escherichia coli strain BL21(DE3) Streptomyces peucetius

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.106
-
 2-chloro-4-nitrophenol pH 8.0, 37°C Streptomyces peucetius
0.138
-
 S-adenosyl-L-methionine pH 8.0, 37°C Streptomyces peucetius
0.335
-
 S-adenosyl-[(3S)-3-amino-3-(1H-tetrazol-5-yl)propyl](methyl)sulfanium pH 8.0, 37°C Streptomyces peucetius

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
S-adenosyl-L-methionine + carminomycin Streptomyces peucetius
-
 S-adenosyl-L-homocysteine + daunorubicin
-
 ?

Organism

Organism UniProt Comment Textmining
Streptomyces peucetius Q06528
-
-

Purification (Commentary)

Purification (Comment) Organism
recombinant N-terminally His-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography and ultrafiltration Streptomyces peucetius

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
additional information the enzyme has been reported to methylate various modified anthracyclines and flavonoids as surrogate substrates. 2-Chloro-4-nitrophenol is a substrate of DnrK. High-throughput DnrK colorimetric assay with the surrogate acceptor 2-chloro-4-nitrophenol and the different cosubstrates. No activity with derivative S-(7-deazaadenosyl)-[(3S)-3-amino-3-(1H-tetrazol-5-yl)propyl](methyl)sulfanium Streptomyces peucetius ?
-
-
S-adenosyl-L-methionine + 2-chloro-4-nitrophenol
-
 Streptomyces peucetius S-adenosyl-L-homocysteine + methyl-2-chloro-4-nitrophenol
-
 ?
S-adenosyl-L-methionine + carminomycin
-
 Streptomyces peucetius S-adenosyl-L-homocysteine + daunorubicin
-
 ?
S-adenosyl-[(3S)-3-amino-3-(1H-tetrazol-5-yl)propyl](methyl)sulfanium + 2-chloro-4-nitrophenol S-adenosyl-[(3S)-3-amino-3-(1H-tetrazol-5-yl)propyl](methyl)sulfanium is a derivative of AdoMet (S-adenosyl-L-methionine) Streptomyces peucetius S-adenosyl-(3S)-3-amino-3-(1H-tetrazol-5-yl)propane-1-thiol + methyl-2-chloro-4-nitrophenol
-
 ?

Synonyms

Synonyms Comment Organism
carminomycin 4-OMT
-
 Streptomyces peucetius
class I methyltransferase
-
 Streptomyces peucetius
DnrK
-
 Streptomyces peucetius

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 assay at Streptomyces peucetius

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.00028
-
 S-adenosyl-L-methionine pH 8.0, 37°C Streptomyces peucetius
0.00032
-
 2-chloro-4-nitrophenol pH 8.0, 37°C Streptomyces peucetius
0.00052
-
 S-adenosyl-[(3S)-3-amino-3-(1H-tetrazol-5-yl)propyl](methyl)sulfanium pH 8.0, 37°C Streptomyces peucetius

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
8
-
 assay at Streptomyces peucetius

Cofactor

Cofactor Comment Organism Structure
additional information design, synthesis, and evaluation of stable, functional AdoMet isosteres that are resistant to the primary contributors to AdoMet degradation (depurination, intramolecular cyclization, and sulfonium epimerization). The AdoMet surrogates to serve as competent enzyme cosubstrates and to bind a prototypical class I model methyltransferase (DnrK) in a manner nearly identical to AdoMet. Half-lives of AdoMet derivatives, overview. Analysis of DnrK ligand-bound structures: DnrK-S-adenosyl-(3S)-3-amino-3-(1H-tetrazol-5-yl)propane-1-thiol and DnrK-S-adenosyl-(3S)-3-amino-3-(1H-tetrazol-5-yl)propane-1-thiol-carminomycin Streptomyces peucetius
S-adenosyl-L-methionine S-adenosyl-L-methionine (AdoMet) is an essential enzyme cosubstrate Streptomyces peucetius

General Information

General Information Comment Organism
physiological function the prototypical class I MT DnrK is a model and is the carminomycin 4-O-ethyltransferase that catalyzes a culminating step in the biosynthesis of the anticancer agent daunorubicin in Streptomyces peucetius Streptomyces peucetius

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
0.0015
-
 S-adenosyl-[(3S)-3-amino-3-(1H-tetrazol-5-yl)propyl](methyl)sulfanium pH 8.0, 37°C Streptomyces peucetius
0.0021
-
 S-adenosyl-L-methionine pH 8.0, 37°C Streptomyces peucetius
0.003
-
 2-chloro-4-nitrophenol pH 8.0, 37°C Streptomyces peucetius