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Literature summary extracted from

  • Dineva, M.A.; Gatunsky, B.; Kasche, V.; Petkov, D.D.
    Phenylacetyl group as enzyme-cleavable aminoprotection of purine nucleosides (1993), Bioorg. Med. Chem. Lett., 3, 2781-2784.
No PubMed abstract available

Application

EC Number Application Comment Organism
3.5.1.11 synthesis despite the relatively weak reactivity of the exocyclic amino group of 2'-deoxyadenosine or 2'-deoxyguanosine under the conditions for nucleotide bond formation, its selective protection is an unavoidable step in oligonucleotide synthesis. The phenylacetyl group can be successfully used as an enzyme-cleavable aminoprotecting group of 2'-deoxyadenosine and 2'-deoxyguanosine. Penicillin amidase would be effective in multiple deprotection of oligonucleotides containing N-phenylacetylated purine nucleobases under mild conditions Escherichia coli

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
3.5.1.11 0.46
-
 N6-phenylacetyl-2'-deoxyadenosine pH 7.8, 25°C Escherichia coli
3.5.1.11 0.67
-
 phenylacetylaspartame pH 7.8, 25°C Escherichia coli
3.5.1.11 0.8
-
 N2-phenylacetyl-2'-deoxyguanosine pH 7.8, 25°C Escherichia coli
3.5.1.11 5.2
-
 phenylacetyl-Gly pH 7.8, 25°C Escherichia coli
3.5.1.11 19
-
 penicillin G pH 7.8, 25°C Escherichia coli

Organism

EC Number Organism UniProt Comment Textmining
3.5.1.11 Escherichia coli
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.5.1.11 N2-phenylacetyl-2'-deoxyguanosine + H2O
-
 Escherichia coli phenylacetic acid + 2'-deoxyguanosine
-
 ?
3.5.1.11 N6-phenylacetyl-2'-deoxyadenosine + H2O
-
 Escherichia coli phenylacetic acid + 2'-deoxyadenosine
-
 ?
3.5.1.11 penicillin G + H2O
-
 Escherichia coli 6-aminopenicillanate + phenylacetic acid
-
 ?
3.5.1.11 phenylacetyl-Gly + H2O
-
 Escherichia coli phenylacetic acid + glycine
-
 ?
3.5.1.11 phenylacetylaspartame + H2O
-
 Escherichia coli phenylacetic acid + aspartame
-
 ?

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
3.5.1.11 2
-
 N6-phenylacetyl-2'-deoxyadenosine pH 7.8, 25°C Escherichia coli
3.5.1.11 18
-
 N2-phenylacetyl-2'-deoxyguanosine pH 7.8, 25°C Escherichia coli
3.5.1.11 35
-
 phenylacetylaspartame pH 7.8, 25°C Escherichia coli
3.5.1.11 47
-
 phenylacetyl-Gly pH 7.8, 25°C Escherichia coli
3.5.1.11 50
-
 penicillin G pH 7.8, 25°C Escherichia coli