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Literature summary for 1.14.20.1 extracted from
- Enzymology of beta-lactam compounds with cephem structure produced by actinomycete (2009), Methods Enzymol., 458, 401-429.
Activating Compound
| Activating Compound | Comment | Organism | Structure |
|---|---|---|---|
| ascorbate | reducing agent stimulates DAOC synthase activity | Actinomyces sp. |  |
| ascorbate | stimulated and stabilized by ascorbate | Amycolatopsis lactamdurans | |
| ascorbate | stimulated and stabilized by ascorbate | Streptomyces clavuligerus | |
| dithiothreitol | stimulated and stabilized by dithiothreitol | Amycolatopsis lactamdurans | |
| dithiothreitol | stimulated and stabilized by dithiothreitol | Streptomyces clavuligerus | |
| DTT | reducing agent stimulates DAOC synthase activity | Actinomyces sp. | |
Application
| Application | Comment | Organism |
|---|---|---|
| biotechnology | production of beta-lactam antibiotics | Actinomyces sp. |
Cloned(Commentary)
| Cloned (Comment) | Organism |
|---|---|
| expressed in Escherichia coli | Amycolatopsis lactamdurans |
| expressed in Escherichia coli | Streptomyces clavuligerus |
| expressed in Escherichia coli | Actinomyces sp. |
Crystallization (Commentary)
| Crystallization (Comment) | Organism |
|---|---|
- |
Streptomyces clavuligerus |
| crystal structure of the DAOC synthase is in trimeric form, C-terminal end of the protein is responsible for the oligomerization process, addition of Fe2+ or 2-oxoglutarate shifts the equilibrium toward the monomeric form that appears to be the active form in solution | Actinomyces sp. |
Protein Variants
| Protein Variants | Comment | Organism |
|---|---|---|
| additional information | mutations to obtain a wider substrate specificity for DAOCS are very important since modification of the DAOCS activity to accept hydrophobic penicillins is of great industrial interest | Actinomyces sp. |
KM Value [mM]
| KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| additional information | - |
additional information | KM-value of Fe2+ is 0.071 mM | Actinomyces sp. | |
| 0.003 | - |
2-oxoglutarate | - |
Amycolatopsis lactamdurans | |
| 0.003 | - |
2-oxoglutarate | - |
Actinomyces sp. | |
| 0.052 | - |
Penicillin N | - |
Amycolatopsis lactamdurans | |
| 0.052 | - |
Penicillin N | - |
Actinomyces sp. | |
Metals/Ions
| Metals/Ions | Comment | Organism | Structure |
|---|---|---|---|
| Fe2+ | essential fpr DAOC synthase activity | Actinomyces sp. | |
| Fe2+ | required, cannot be substituted by other divalent metal ions | Amycolatopsis lactamdurans | |
| Fe2+ | required, cannot be substituted by other divalent metal ions | Streptomyces clavuligerus | |
Molecular Weight [Da]
| Molecular Weight [Da] | Molecular Weight Maximum [Da] | Comment | Organism |
|---|---|---|---|
| 28900 | - |
DAOCS monomer from Streptomyces | Actinomyces sp. |
| 28900 | - |
1 * 28900, recombinant enzyme | Streptomyces clavuligerus |
| 30966 | - |
3 * 30966, DAOCS is in equilibrium with a trimeric form which is the form that crystallizes | Streptomyces clavuligerus |
Natural Substrates/ Products (Substrates)
| Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| additional information | Amycolatopsis lactamdurans | does not use isopenicillin N or 6-aminopenicillanic acid as substrates, the natural enzyme is only able to use 2-oxoglutarate but not 2-ketobutyrate, 3-ketoadipate, 2-ketohexanoic acid, or 2-keto-4-methylpentanoic acid as cosubstrates | ? | - |
? | |
| additional information | Streptomyces clavuligerus | does not use isopenicillin N or 6-aminopenicillanic acid as substrates, the natural enzyme is only able to use 2-oxoglutarate but not 2-ketobutyrate, 3-ketoadipate, 2-ketohexanoic acid, or 2-keto-4-methylpentanoic acid as cosubstrates | ? | - |
? | |
| additional information | Amycolatopsis lactamdurans NRRL3802 | does not use isopenicillin N or 6-aminopenicillanic acid as substrates, the natural enzyme is only able to use 2-oxoglutarate but not 2-ketobutyrate, 3-ketoadipate, 2-ketohexanoic acid, or 2-keto-4-methylpentanoic acid as cosubstrates | ? | - |
? | |
| additional information | Streptomyces clavuligerus ATCC 27064 | does not use isopenicillin N or 6-aminopenicillanic acid as substrates, the natural enzyme is only able to use 2-oxoglutarate but not 2-ketobutyrate, 3-ketoadipate, 2-ketohexanoic acid, or 2-keto-4-methylpentanoic acid as cosubstrates | ? | - |
? | |
| N-adipyl-6-aminopenicillanic acid + 2-oxoglutarate + O2 | Amycolatopsis lactamdurans | - |
N7-adipylaminodeacetoxycephalosporanic acid + succinate + CO2 + H2O | - |
? | |
| N-adipyl-6-aminopenicillanic acid + 2-oxoglutarate + O2 | Streptomyces clavuligerus | - |
N7-adipylaminodeacetoxycephalosporanic acid + succinate + CO2 + H2O | - |
? | |
| N-adipyl-6-aminopenicillanic acid + 2-oxoglutarate + O2 | Amycolatopsis lactamdurans NRRL3802 | - |
N7-adipylaminodeacetoxycephalosporanic acid + succinate + CO2 + H2O | - |
? | |
| N-adipyl-6-aminopenicillanic acid + 2-oxoglutarate + O2 | Streptomyces clavuligerus ATCC 27064 | - |
N7-adipylaminodeacetoxycephalosporanic acid + succinate + CO2 + H2O | - |
? | |
| penicillin N + 2-oxoglutarate + O2 | Amycolatopsis lactamdurans | - |
deacetoxycephalosporin C + succinate + CO2 + H2O | - |
? | |
| penicillin N + 2-oxoglutarate + O2 | Streptomyces clavuligerus | - |
deacetoxycephalosporin C + succinate + CO2 + H2O | - |
? | |
| penicillin N + 2-oxoglutarate + O2 | Actinomyces sp. | ring expansion of penicillin N to a six member cephem ring, the natural enzyme is only able to use 2-oxoglutarate but not 2-oxobutyrate, 3-oxoadipate, 2-oxohexanoic acid or 2-oxo-4-methylpentanoic acid as cosubstrates | deacetoxycephalosporin C + succinate + CO2 + H2O | - |
? | |
| penicillin N + 2-oxoglutarate + O2 | Amycolatopsis lactamdurans NRRL3802 | - |
deacetoxycephalosporin C + succinate + CO2 + H2O | - |
? | |
| penicillin N + 2-oxoglutarate + O2 | Streptomyces clavuligerus ATCC 27064 | - |
deacetoxycephalosporin C + succinate + CO2 + H2O | - |
? | |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Actinomyces sp. | - |
- |
- |
| Amycolatopsis lactamdurans | - |
- |
- |
| Amycolatopsis lactamdurans NRRL3802 | - |
- |
- |
| Streptomyces clavuligerus | - |
strain ATCC27064 | - |
| Streptomyces clavuligerus ATCC 27064 | - |
strain ATCC27064 | - |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| additional information | does not use isopenicillin N or 6-aminopenicillanic acid as substrates, the natural enzyme is only able to use 2-oxoglutarate but not 2-ketobutyrate, 3-ketoadipate, 2-ketohexanoic acid, or 2-keto-4-methylpentanoic acid as cosubstrates | Amycolatopsis lactamdurans | ? | - |
? | |
| additional information | does not use isopenicillin N or 6-aminopenicillanic acid as substrates, the natural enzyme is only able to use 2-oxoglutarate but not 2-ketobutyrate, 3-ketoadipate, 2-ketohexanoic acid, or 2-keto-4-methylpentanoic acid as cosubstrates | Streptomyces clavuligerus | ? | - |
? | |
| additional information | does not use isopenicillin N or 6-aminopenicillanic acid as substrates, the natural enzyme is only able to use 2-oxoglutarate but not 2-ketobutyrate, 3-ketoadipate, 2-ketohexanoic acid, or 2-keto-4-methylpentanoic acid as cosubstrates | Amycolatopsis lactamdurans NRRL3802 | ? | - |
? | |
| additional information | does not use isopenicillin N or 6-aminopenicillanic acid as substrates, the natural enzyme is only able to use 2-oxoglutarate but not 2-ketobutyrate, 3-ketoadipate, 2-ketohexanoic acid, or 2-keto-4-methylpentanoic acid as cosubstrates | Streptomyces clavuligerus ATCC 27064 | ? | - |
? | |
| N-adipyl-6-aminopenicillanic acid + 2-oxoglutarate + O2 | - |
Amycolatopsis lactamdurans | N7-adipylaminodeacetoxycephalosporanic acid + succinate + CO2 + H2O | - |
? | |
| N-adipyl-6-aminopenicillanic acid + 2-oxoglutarate + O2 | - |
Streptomyces clavuligerus | N7-adipylaminodeacetoxycephalosporanic acid + succinate + CO2 + H2O | - |
? | |
| N-adipyl-6-aminopenicillanic acid + 2-oxoglutarate + O2 | - |
Amycolatopsis lactamdurans NRRL3802 | N7-adipylaminodeacetoxycephalosporanic acid + succinate + CO2 + H2O | - |
? | |
| N-adipyl-6-aminopenicillanic acid + 2-oxoglutarate + O2 | - |
Streptomyces clavuligerus ATCC 27064 | N7-adipylaminodeacetoxycephalosporanic acid + succinate + CO2 + H2O | - |
? | |
| penicillin N + 2-oxoglutarate + O2 | - |
Amycolatopsis lactamdurans | deacetoxycephalosporin C + succinate + CO2 + H2O | - |
? | |
| penicillin N + 2-oxoglutarate + O2 | - |
Streptomyces clavuligerus | deacetoxycephalosporin C + succinate + CO2 + H2O | - |
? | |
| penicillin N + 2-oxoglutarate + O2 | ring expansion of penicillin N to a six member cephem ring, the natural enzyme is only able to use 2-oxoglutarate but not 2-oxobutyrate, 3-oxoadipate, 2-oxohexanoic acid or 2-oxo-4-methylpentanoic acid as cosubstrates | Actinomyces sp. | deacetoxycephalosporin C + succinate + CO2 + H2O | - |
? | |
| penicillin N + 2-oxoglutarate + O2 | - |
Amycolatopsis lactamdurans NRRL3802 | deacetoxycephalosporin C + succinate + CO2 + H2O | - |
? | |
| penicillin N + 2-oxoglutarate + O2 | - |
Streptomyces clavuligerus ATCC 27064 | deacetoxycephalosporin C + succinate + CO2 + H2O | - |
? | |
Subunits
| Subunits | Comment | Organism |
|---|---|---|
| monomer | 1 * 28900, recombinant enzyme | Streptomyces clavuligerus |
| monomer | DAOC synthase, recombinant DAOCS of Streptomyces clavuligerus is a monomer but is in equilibrium with a trimeric form of 92900 Da | Actinomyces sp. |
| trimer | 3 * 30966, DAOCS is in equilibrium with a trimeric form which is the form that crystallizes | Streptomyces clavuligerus |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| DAOC synthase | - |
Actinomyces sp. |
| DAOCS | - |
Amycolatopsis lactamdurans |
| DAOCS | - |
Streptomyces clavuligerus |
| DAOCS | - |
Actinomyces sp. |
| deacetoxycephalosporin C synthase | - |
Amycolatopsis lactamdurans |
| deacetoxycephalosporin C synthase | - |
Streptomyces clavuligerus |
| deacetoxycephalosporin-C synthase | - |
Actinomyces sp. |
| expendase | - |
Actinomyces sp. |
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