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Literature summary for 3.5.1.11 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
Search for more literature for 3.5.1.11

Application

Application Comment Organism
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]

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

Organism

Organism UniProt Comment Textmining
Escherichia coli
-
-
-

Substrates and Products (Substrate)

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

Turnover Number [1/s]

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