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Literature summary extracted from
- Engineering deacetoxycephalosporin C synthase as a catalyst for the bioconversion of penicillins (2017), J. Ind. Microbiol. Biotechnol., 44, 705-710 .
Activating Compound
| EC Number | Activating Compound | Comment | Organism | Structure |
|---|---|---|---|---|
| 1.14.20.1 | ascorbate | required | Streptomyces clavuligerus |  |
| 1.14.20.1 | ascorbate | required | Acremonium chrysogenum | |
| 1.14.20.1 | ascorbate | required | Amycolatopsis lactamdurans | |
Application
| EC Number | Application | Comment | Organism |
|---|---|---|---|
| 1.14.20.1 | synthesis | bioconversion of penicillins to cephalosporins using deacetoxycephalosporin C synthase (DAOCS) is an alternative and environmentally friendly process for production of 7-aminodeacetoxycephalosporanic acid (7-ADCA), a key intermediate of many clinically useful semisynthetic cephalosporins | Streptomyces clavuligerus |
| 1.14.20.1 | synthesis | bioconversion of penicillins to cephalosporins using deacetoxycephalosporin C synthase (DAOCS) is an alternative and environmentally friendly process for production of 7-aminodeacetoxycephalosporanic acid (7-ADCA), a key intermediate of many clinically useful semisynthetic cephalosporins | Acremonium chrysogenum |
| 1.14.20.1 | synthesis | bioconversion of penicillins to cephalosporins using deacetoxycephalosporin C synthase (DAOCS) is an alternative and environmentally friendly process for production of 7-aminodeacetoxycephalosporanic acid (7-ADCA), a key intermediate of many clinically useful semisynthetic cephalosporins | Amycolatopsis lactamdurans |
Cloned(Commentary)
| EC Number | Cloned (Comment) | Organism |
|---|---|---|
| 1.14.20.1 | gene cefE, recombinant expression in Escherichia coli BW25311. Recombinant expression of a hybrid enzyme,with parts from the enzymes of Streptomyces clavuligerus and Nocardia lactamdurans, in Streptomyces lividans strain W25, the recombinant enzyme is capable of converting penicillin G to G-7-aminodeacetoxycephalosporanic acid (G-7-ADCA) | Amycolatopsis lactamdurans |
| 1.14.20.1 | gene cefE, recombinant expression in Escherichia coli strain BW25311, functional recombinant expression of scDAOCS in Penicillium chrysogenum leading to expandase activity for penicillin N in the transfected cells. But only penicillin V is produced under the fermentation conditions, indicating that the industrial application of DAOCS is restricted by its low activities toward penicillin analogues other than penicillin N. In Penicillium chrysogenum strains expressing scDAOCS, a fermentation process is developed to produce adipyl-7-ADCA and adipyl-7-ACA, which can be converted to 7-ADCA and 7-ACA by glutaryl acylase. Recombinant expression of a hybrid enzyme,with parts from the enzymes of Streptomyces clavuligerus and Nocardia lactamdurans, in Streptomyces lividans strain W25, the recombinant enzyme is capable of converting penicillin G to G-7-aminodeacetoxycephalosporanic acid (G-7-ADCA). Recombinant expression of Streptomyces clavuligerus scDAOCS in a cefEF-disrupted cephalosporin C production Acremonium chrysogenum strain, which converts penicillin N accumulated in the disruption strain to deacetoxycephalosporin C | Streptomyces clavuligerus |
| 1.14.20.1 | gene cefEF, recombinant expression in Escherichia coli, functional recombinant expression of acDAOCS in Penicillium chrysogenum strains leads to a fermentation process developed to produce adipyl-7-ADCA and adipyl-7-ACA, which can be converted to 7-ADCA and 7-ACA by glutaryl acylase | Acremonium chrysogenum |
Protein Variants
| EC Number | Protein Variants | Comment | Organism |
|---|---|---|---|
| 1.14.20.1 | C155Y/Y184H/S261M/V275I/C281Y/I305M | site-directed mutagenesis, the mutant shows 87fold increased kcat/Km for penicillin G compared to the wild-type | Streptomyces clavuligerus |
| 1.14.20.1 | C155Y/Y184H/V275I/C281Y | site-directed mutagenesis, quaternary mutant from error-prone PCR, the mutant shows 41fold increased kcat/Km for penicillin G compared to the wild-type | Streptomyces clavuligerus |
| 1.14.20.1 | M73T/C155Y/Y184H/T213V/V275I/C281Y/I305M | site-directed mutagenesis, the mutant shows 22fold increased specific activity and 81fold increased kcat/Km for penicillin G compared to the wild-type | Streptomyces clavuligerus |
| 1.14.20.1 | additional information | rational mutational approach to generate an engineered strain for enhanced production of from penicillin G, e.g. mutant FF8 from gene shuffling with 118fold increase in kcat/Km | Streptomyces clavuligerus |
| 1.14.20.1 | additional information | recombinant expression of Streptomyces clavuligerus scDAOCS in a cefEF-disrupted cephalosporin C production Acremonium chrysogenum strain, which converts penicillin N accumulated in the disruption strain to deacetoxycephalosporin C | Acremonium chrysogenum |
Metals/Ions
| EC Number | Metals/Ions | Comment | Organism | Structure |
|---|---|---|---|---|
| 1.14.20.1 | Fe2+ | dependent on, required for catalysis | Streptomyces clavuligerus | |
| 1.14.20.1 | Fe2+ | dependent on, required for catalysis | Acremonium chrysogenum | |
| 1.14.20.1 | Fe2+ | dependent on, required for catalysis | Amycolatopsis lactamdurans | |
Natural Substrates/ Products (Substrates)
| EC Number | Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.14.20.1 | penicillin N + 2-oxoglutarate + O2 | Streptomyces clavuligerus | - |
deacetoxycephalosporin C + succinate + CO2 + H2O | - |
? | |
| 1.14.20.1 | penicillin N + 2-oxoglutarate + O2 | Acremonium chrysogenum | - |
deacetoxycephalosporin C + succinate + CO2 + H2O | - |
? | |
| 1.14.20.1 | penicillin N + 2-oxoglutarate + O2 | Amycolatopsis lactamdurans | - |
deacetoxycephalosporin C + succinate + CO2 + H2O | - |
? | |
| 1.14.20.1 | penicillin N + 2-oxoglutarate + O2 | Streptomyces clavuligerus ATCC 27064 | - |
deacetoxycephalosporin C + succinate + CO2 + H2O | - |
? | |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 1.14.20.1 | Acremonium chrysogenum | P11935 | i.e. Cephalosporium acremonium | - |
| 1.14.20.1 | Amycolatopsis lactamdurans | Q03047 | - |
- |
| 1.14.20.1 | Streptomyces clavuligerus | P18548 | - |
- |
| 1.14.20.1 | Streptomyces clavuligerus ATCC 27064 | P18548 | - |
- |
Purification (Commentary)
| EC Number | Purification (Comment) | Organism |
|---|---|---|
| 1.14.20.1 | recombinant enzyme from Escherichia coli | Streptomyces clavuligerus |
| 1.14.20.1 | recombinant enzyme from Escherichia coli | Acremonium chrysogenum |
| 1.14.20.1 | recombinant enzyme from Escherichia coli | Amycolatopsis lactamdurans |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.14.20.1 | additional information | purified recombinant enzyme DAOCS expressed in Escherichia coli catalyzes the ring expansion of penicillin N but shows no hydroxylation activity for DAOC, EC 1.14.11.26 | Streptomyces clavuligerus | ? | - |
? | |
| 1.14.20.1 | additional information | purified recombinant enzyme DAOCS expressed in Escherichia coli catalyzes the ring expansion of penicillin N but shows no hydroxylation activity for DAOC, EC 1.14.11.26 | Streptomyces clavuligerus ATCC 27064 | ? | - |
? | |
| 1.14.20.1 | penicillin G + 2-oxoglutarate + O2 | - |
Streptomyces clavuligerus | 7-phenylacetylaminocephalosporanate + succinate + CO2 + H2O | - |
? | |
| 1.14.20.1 | penicillin G + 2-oxoglutarate + O2 | - |
Acremonium chrysogenum | 7-phenylacetylaminocephalosporanate + succinate + CO2 + H2O | - |
? | |
| 1.14.20.1 | penicillin G + 2-oxoglutarate + O2 | - |
Amycolatopsis lactamdurans | 7-phenylacetylaminocephalosporanate + succinate + CO2 + H2O | - |
? | |
| 1.14.20.1 | penicillin G + 2-oxoglutarate + O2 | - |
Streptomyces clavuligerus ATCC 27064 | 7-phenylacetylaminocephalosporanate + succinate + CO2 + H2O | - |
? | |
| 1.14.20.1 | penicillin N + 2-oxoglutarate + O2 | - |
Streptomyces clavuligerus | deacetoxycephalosporin C + succinate + CO2 + H2O | - |
? | |
| 1.14.20.1 | penicillin N + 2-oxoglutarate + O2 | - |
Acremonium chrysogenum | deacetoxycephalosporin C + succinate + CO2 + H2O | - |
? | |
| 1.14.20.1 | penicillin N + 2-oxoglutarate + O2 | - |
Amycolatopsis lactamdurans | deacetoxycephalosporin C + succinate + CO2 + H2O | - |
? | |
| 1.14.20.1 | penicillin N + 2-oxoglutarate + O2 | ring expansion of penicillin N | Streptomyces clavuligerus | deacetoxycephalosporin C + succinate + CO2 + H2O | - |
? | |
| 1.14.20.1 | penicillin N + 2-oxoglutarate + O2 | - |
Streptomyces clavuligerus ATCC 27064 | deacetoxycephalosporin C + succinate + CO2 + H2O | - |
? | |
| 1.14.20.1 | penicillin N + 2-oxoglutarate + O2 | ring expansion of penicillin N | Streptomyces clavuligerus ATCC 27064 | deacetoxycephalosporin C + succinate + CO2 + H2O | - |
? | |
Synonyms
| EC Number | Synonyms | Comment | Organism |
|---|---|---|---|
| 1.14.20.1 | cefE | - |
Streptomyces clavuligerus |
| 1.14.20.1 | cefE | - |
Amycolatopsis lactamdurans |
| 1.14.20.1 | cefEF | - |
Acremonium chrysogenum |
| 1.14.20.1 | DAOCS | - |
Streptomyces clavuligerus |
| 1.14.20.1 | DAOCS | - |
Acremonium chrysogenum |
| 1.14.20.1 | DAOCS | - |
Amycolatopsis lactamdurans |
| 1.14.20.1 | deacetoxycephalosporin C synthase | - |
Streptomyces clavuligerus |
| 1.14.20.1 | deacetoxycephalosporin C synthase | - |
Acremonium chrysogenum |
| 1.14.20.1 | deacetoxycephalosporin C synthase | - |
Amycolatopsis lactamdurans |
| 1.14.20.1 | expandase | - |
Acremonium chrysogenum |
General Information
| EC Number | General Information | Comment | Organism |
|---|---|---|---|
| 1.14.20.1 | evolution | the enzyme belongs to the iron- and 2-oxoglutarate-dependent oxidases | Streptomyces clavuligerus |
| 1.14.20.1 | evolution | the enzyme belongs to the iron- and 2-oxoglutarate-dependent oxidases | Acremonium chrysogenum |
| 1.14.20.1 | evolution | the enzyme belongs to the iron- and 2-oxoglutarate-dependent oxidases | Amycolatopsis lactamdurans |
| 1.14.20.1 | physiological function | Cephalosporium acremonium expandase is a bifunctional enzyme, penicillin expandase, which catalyzes the ring expansion of penicillin N and the hydroxylation of deacetoxycephalosporin C (DAOC) to deacetylcephalosporin C (DAC). 2-oxoglutarate, Fe2+ and O2 are required for its catalytic activity. The enzyme is encoded by gene cefEF | Acremonium chrysogenum |
| 1.14.20.1 | physiological function | Cephalosporium acremonium expandase is a bifunctional enzyme, which catalyzes the ring expansion of penicillin N and the hydroxylation of deacetoxycephalosporin C (DAOC) to deacetylcephalosporin C (DAC). 2-oxoglutarate, Fe2+ and O2 are required for its catalytic activity. The enzyme is encoded by gene cefEF | Amycolatopsis lactamdurans |
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