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Enzyme Nomenclature
Information on EC 4.2.1.108 - ectoine synthase
for references in articles please use BRENDA:EC4.2.1.108
Word Map on EC 4.2.1.108
- 4.2.1.108
-
halophil
-
hydroxyectoine
- halomonas
-
diaminobutyric
-
ectabc
- elongata
-
osmoprotectant
-
salt-sensitive
- salexigens
-
halotolerant
-
methanotrophs
-
methylophaga
-
methylobacter
- alcalophilus
-
nada
-
non-halophilic
-
sphingopyxis
- alaskensis
-
chromohalobacter
-
cold-adapted
- biotechnology
-
osmoregulated
- 2,4-diaminobutyrate
-
methylomicrobium
-
deep-sea
- industry
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
4.2.1.108
-
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RECOMMENDED NAME
GeneOntology No.
ectoine synthase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
N4-acetyl-L-2,4-diaminobutanoate = L-ectoine + H2O
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
condensation
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
N4-acetyl-L-2,4-diaminobutanoate hydro-lyase (L-ectoine-forming)
Ectoine is an osmoprotectant that is found in halophilic eubacteria. This enzyme is part of the ectoine biosynthesis pathway and only acts in the direction of ectoine formation. cf. EC 3.5.4.44, ectoine hydrolase.
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CAS REGISTRY NUMBER
COMMENTARY
130457-09-9
-
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
formerly Halomonas elongata, strain DSM 3043, gene ectC encoded in the ectABC gene cluster
SwissProt
no activity in Aneurinibacillus aneurinilyticus DSM 5562
formerly Bacillus aneurinilyticus
-
-
strain DSM 33, gene ectC encoded in the ectABC gene cluster
SwissProt
the ectABC gene cluster expressed in Escherichia coli M15 (pREP4)
TrEMBL
the ectABC gene cluster expressed in Escherichia coli M15 (pREP4)
TrEMBL
ectABCask gene cluster sequence; 20Z, obligate methanotroph, gene ectC
SwissProt
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
metabolism
physiological function
malfunction
-
in Halomonas elongata mutant strains deficient in ectA, encoding L-2,4-diaminobutyric acid acetyltransferase, no ectoine synthesis is obeserved
malfunction
-
in Halomonas elongata mutant strains deficient in ectA, encoding L-2,4-diaminobutyric acid acetyltransferase, no ectoine synthesis is obeserved
-
metabolism
-
ectoine synthase is involved in the biosynthetic pathway of L-ectoine and (S,S)-beta-hydroxyectoine, involvement of ectoine synthase in 5-amino-3,4-dihydro-2H-pyrrole-2-carboxylate biosynthesis in vitro
metabolism
the enzyme is involved in ectoine biosynthesis
metabolism
-
ectoine synthase is involved in the biosynthetic pathway of L-ectoine and (S,S)-beta-hydroxyectoine, involvement of ectoine synthase in 5-amino-3,4-dihydro-2H-pyrrole-2-carboxylate biosynthesis in vitro
-
physiological function
-
extraordinary protective properties of 5-amino-3,4-dihydro-2H-pyrrole-2-carboxylate produced by ectoine synthase
physiological function
-
extraordinary protective properties of 5-amino-3,4-dihydro-2H-pyrrole-2-carboxylate produced by ectoine synthase
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
N4-acetyl-L-2,4-diaminobutyrate
2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid + H2O
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
final step in L-ectoine biosynthesis, L-ectoine acts as an osmoprotectant
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
i.e. 1,4,5,6-tetrahydro-2-methyl-4-pyrimidine carboxylic acid
NMR product identification
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
final step in L-ectoine biosynthesis, L-ectoine acts as an osmoprotectant
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
i.e. 1,4,5,6-tetrahydro-2-methyl-4-pyrimidine carboxylic acid
NMR product identification
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
final step in L-ectoine biosynthesis, L-ectoine is the compatible solute in the cell
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
final step in L-ectoine biosynthesis, pathway overview
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
final step in L-ectoine biosynthesis, pathway overview, L-ectoine is the main compatible solute in the organism with a cytoplasmic concentration of 1-2 M
-
-
r
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
i.e. 1,4,5,6-tetrahydro-2-methyl-4-pyrimidine carboxylic acid
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
i.e. 1,4,5,6-tetrahydro-2-methyl-4-pyrimidine carboxylic acid
NMR and thin layer chromatography product identification
-
r
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
i.e. 1,4,5,6-tetrahydro-2-methyl-4-pyrimidine carboxylic acid, circularization, L-ectoine as an effective osmoprotectant, the enzyme shows absolute substrate specificity, reversibility of the reaction is not detected but might be below detection range
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
final step in L-ectoine biosynthesis, pathway overview
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
i.e. 1,4,5,6-tetrahydro-2-methyl-4-pyrimidine carboxylic acid, circularization, L-ectoine as an effective osmoprotectant, the enzyme shows absolute substrate specificity, reversibility of the reaction is not detected but might be below detection range
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
final step in L-ectoine biosynthesis, L-ectoine is the compatible solute in the cell
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
i.e. 1,4,5,6-tetrahydro-2-methyl-4-pyrimidine carboxylic acid
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
final step in L-ectoine biosynthesis, pathway overview
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
i.e. 1,4,5,6-tetrahydro-2-methyl-4-pyrimidine carboxylic acid, circularization, L-ectoine as an effective osmoprotectant, the enzyme shows absolute substrate specificity, reversibility of the reaction is not detected but might be below detection range
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
final step in L-ectoine biosynthesis, pathway overview
-
-
r
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
i.e. 1,4,5,6-tetrahydro-2-methyl-4-pyrimidine carboxylic acid
NMR and TLC product identification
-
r
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
final step in L-ectoine biosynthesis, pathway overview
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
i.e. 1,4,5,6-tetrahydro-2-methyl-4-pyrimidine carboxylic acid
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
final step in L-ectoine biosynthesis, pathway overview
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
i.e. 1,4,5,6-tetrahydro-2-methyl-4-pyrimidine carboxylic acid
NMR product identification
-
r
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
final step in L-ectoine biosynthesis, L-ectoine acts as an osmoprotectant
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
i.e. 1,4,5,6-tetrahydro-2-methyl-4-pyrimidine carboxylic acid
NMR identification
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
final step in L-ectoine biosynthesis, L-ectoine acts as an osmoprotectant
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
i.e. 1,4,5,6-tetrahydro-2-methyl-4-pyrimidine carboxylic acid
NMR identification
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
final step in L-ectoine biosynthesis, L-ectoine acts as an osmoprotectant
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
i.e. 1,4,5,6-tetrahydro-2-methyl-4-pyrimidine carboxylic acid
NMR product identification
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
final step in L-ectoine biosynthesis, L-ectoine acts as an osmoprotectant
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
i.e. 1,4,5,6-tetrahydro-2-methyl-4-pyrimidine carboxylic acid
NMR product identification
-
?
D,L-4,5-dihydro-2-methylimidazole-4-carboxylate + H2O
?
-
-
-
-
r
L-glutamine
5-amino-3,4-dihydro-2H-pyrrole-2-carboxylate + H2O
-
-
-
-
r
N4-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
an intramolecular condensation reaction
i.e. 1,4,5,6-tetrahydro-2-methyl-4-pyrimidine carboxylic acid, over 95% conversion by the recombinant ectoine synthase
-
r
N4-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
an intramolecular condensation reaction
i.e. 1,4,5,6-tetrahydro-2-methyl-4-pyrimidine carboxylic acid, over 95% conversion by the recombinant ectoine synthase
-
r
N4-acetyl-L-2,4-diaminobutyrate
2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid + H2O
-
-
-
?
N4-acetyl-L-2,4-diaminobutyrate
2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid + H2O
-
-
-
?
N4-acetyl-L-2,4-diaminobutyrate
L-ectoine + H2O
-
-
-
?
additional information
?
-
-
ectoine synthase accepts more than one substrate and is a reversible enzyme able to catalyze both the intramolecular condensation into and the hydrolytic cleavage of cyclic amino acid derivatives. It forms 5-amino-3,4-dihydro-2H-pyrrole-2-carboxylate, ADPC, by cyclic condensation of glutamine in a reversible reaction. A number of ectoine derivatives, in particular 4,5-dihydro-2-methylimidazole-4-carboxylate and L-homoectoine, are also cleaved by ectoine synthase. Proposed reaction mechanism leading to L-ectoine and 5-amino-3,4-dihydro-2H-pyrrole-2-carboxylate, respectively, catalyzed by ectoine synthase, overview
-
-
-
additional information
?
-
-
ectoine synthase accepts more than one substrate and is a reversible enzyme able to catalyze both the intramolecular condensation into and the hydrolytic cleavage of cyclic amino acid derivatives. It forms 5-amino-3,4-dihydro-2H-pyrrole-2-carboxylate, ADPC, by cyclic condensation of glutamine in a reversible reaction. A number of ectoine derivatives, in particular 4,5-dihydro-2-methylimidazole-4-carboxylate and L-homoectoine, are also cleaved by ectoine synthase. Proposed reaction mechanism leading to L-ectoine and 5-amino-3,4-dihydro-2H-pyrrole-2-carboxylate, respectively, catalyzed by ectoine synthase, overview
-
-
-
additional information
?
-
the enzyme is osmoregulated in response to medium salinity allowing the organism to live in environments with high concentration of osmolytes
-
-
-
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
N4-acetyl-L-2,4-diaminobutyrate
2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid + H2O
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
final step in L-ectoine biosynthesis, L-ectoine acts as an osmoprotectant
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
Q9ZEU6
final step in L-ectoine biosynthesis, L-ectoine acts as an osmoprotectant
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
final step in L-ectoine biosynthesis, L-ectoine is the compatible solute in the cell
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
final step in L-ectoine biosynthesis, pathway overview
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
final step in L-ectoine biosynthesis, pathway overview, L-ectoine is the main compatible solute in the organism with a cytoplasmic concentration of 1-2 M
-
-
r
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
final step in L-ectoine biosynthesis, pathway overview
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
final step in L-ectoine biosynthesis, L-ectoine is the compatible solute in the cell
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
final step in L-ectoine biosynthesis, pathway overview
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
final step in L-ectoine biosynthesis, pathway overview
-
-
r
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
O06061
final step in L-ectoine biosynthesis, pathway overview
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
Q4JQJ3
final step in L-ectoine biosynthesis, pathway overview
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
Q9AP33
final step in L-ectoine biosynthesis, L-ectoine acts as an osmoprotectant
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
final step in L-ectoine biosynthesis, L-ectoine acts as an osmoprotectant
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
final step in L-ectoine biosynthesis, L-ectoine acts as an osmoprotectant
-
-
?
4-N-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
final step in L-ectoine biosynthesis, L-ectoine acts as an osmoprotectant
-
-
?
N4-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
an intramolecular condensation reaction
-
-
r
N4-acetyl-L-2,4-diaminobutanoate
L-ectoine + H2O
-
an intramolecular condensation reaction
-
-
r
N4-acetyl-L-2,4-diaminobutyrate
2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid + H2O
A5A5G3
-
-
-
?
N4-acetyl-L-2,4-diaminobutyrate
2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid + H2O
A5A5G3
-
-
-
?
N4-acetyl-L-2,4-diaminobutyrate
L-ectoine + H2O
A5A5G3
-
-
-
?
additional information
?
-
O06061
the enzyme is osmoregulated in response to medium salinity allowing the organism to live in environments with high concentration of osmolytes
-
-
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
NaCl
additional information
-
the enzyme is not affected by Mg2+, Ca2+, Mn2+, Li+, K+, and NH4+
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
high osmolarity induces the enzyme expression, requirements
-
additional information
high osmolarity induces the enzyme expression, requirements
-
additional information
high salinity/osmolarity of the medium induces enzyme expression
-
additional information
enzyme expression is 12fold induced by NaCl at 1 M
-
additional information
high osmolarity induces the enzyme expression, requirements
-
additional information
-
high osmolarity induces the enzyme expression, requirements
-
additional information
-
high osmolarity induces the enzyme expression, requirements
-
additional information
-
high osmolarity induces the enzyme expression, requirements
-
additional information
-
high osmolarity induces the enzyme expression, requirements
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
8.4
4-N-acetyl-L-2,4-diaminobutanoate
-
pH 9.5, 15°C, in presence of 0.77 M NaCl
11
4-N-acetyl-L-2,4-diaminobutanoate
-
pH 9.5, 15°C, in presence of 0.05 M NaCl
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.16
-
purified recombinant enzyme, substrate is 4,5-dihydro-2-methylimidazole-4-carboxylate, hydrolytic reaction, pH 8.5, 21°C
0.3
-
purified recombinant enzyme, substrate is 5-amino-3,4-dihydro-2H-pyrrole-2-carboxylate, hydrolytic reaction, pH 8.5, 21°C
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
37
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0 - 30
-
the temperature optimum shifts from 0°C to 30°C with increasing NaCl concentration
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
cells are grown in an atmosphere of air-methane 1:1 in 1 M NaCl
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PDB
SCOP
CATH
UNIPROT
ORGANISM
Paenibacillus lautus;
Sphingopyxis alaskensis (strain DSM 13593 / LMG 18877 / RB2256);
Q1GNW6
Sphingopyxis alaskensis (strain DSM 13593 / LMG 18877 / RB2256);
Q1GNW6
Sphingopyxis alaskensis (strain DSM 13593 / LMG 18877 / RB2256);
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
native enzyme by ammonium sulfate fractionation, hydrophobic interaction chromatography, ultrafiltration, and hydroxylapatite chromatography, in presence of 1 mM L-2,4-diaminobutanoate and over 2 M NaCl to homogeneity
-
recombinant His6-tagged ectoine synthase from Escherichia coli strain BL21(DE3) by nickel affinity chromatography
-
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression of His6-tagged ectoine synthase in Escherichia coli strain BL21(DE3)
-
functional expression in transgenic Nicotiana tabaccum BY2 cells using the Agrobacterium tumefaciens infection system
-
gene ectC encoded in the ectABC gene cluster, functional expression in Escherichia coli
gene ectC located in the singel operon ectABCask, DNA sequence determination and analysis, genetic organization, expression in Escherichia coli strain X1-Blue
gene ectC, DNA and amino acid sequence determination and analysis, genetic mapping and organization, functional expression in Escherichia coli, the recombinant enzyme expression is osmoregulated in response to medium salinity in Escherichia coli
gene ectC, DNA and amino acid sequence determination and analysis, phylogenetic analysis and genetic organization
gene ectC, encoded in the ectABC gene cluster, sequence determination and analysis, phylogenetic analysis, DNA sequence comparison, expression in Escherichia coli
the ectABC gene cluster is expressed in Escherichia coli M15 (pREP4) by vector pQE30
gene ectC, DNA and amino acid sequence determination and analysis, phylogenetic analysis and genetic organization
gene ectC, DNA and amino acid sequence determination and analysis, phylogenetic analysis and genetic organization
gene ectC, DNA and amino acid sequence determination and analysis, phylogenetic analysis and genetic organization
gene ectC, DNA and amino acid sequence determination and analysis, phylogenetic analysis and genetic organization
gene ectC, DNA and amino acid sequence determination and analysis, phylogenetic analysis and genetic organization
gene ectC, DNA and amino acid sequence determination and analysis, phylogenetic analysis and genetic organization
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
-
expression in transgenic Nicotiana tabacum BY2 cells increases the osmotolerance and growth rate of the cells under hyperosmotic conditions
additional information
-
construction of enzyme-deficient strains by gene ectC inframe deletion though the splicing-by-overlap-extension PCR technique
additional information
-
construction of enzyme-deficient strains by gene ectC inframe deletion though the splicing-by-overlap-extension PCR technique
-
additional information
-
expression in transgenic Nicotiana tabacum BY2 cells increases the osmotolerance and growth rate of the cells under hyperosmotic conditions
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
biotechnology
industry
biotechnology
inducible recombinant enzyme expression in Escherichia coli confers the capability to grow on high concentration of osmolytes by increasing the osmotolerance via L-ectoine production
biotechnology
ectoine has importance in dermopharmacy as anti ageing agents in skin creams, as components of shampoo, for oral care and as adjuvants for vaccines
biotechnology
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ectoine has importance in dermopharmacy as anti ageing agents in skin creams, as components of shampoo, for oral care and as adjuvants for vaccines
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industry
the engineered Escherichia coli strain has potential industrial application since it produces ectoine at high rates and can avoid the complex down streaming process associated with the conventional bioprocess
industry
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the engineered Escherichia coli strain has potential industrial application since it produces ectoine at high rates and can avoid the complex down streaming process associated with the conventional bioprocess
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LINKS TO OTHER DATABASES (specific for EC-Number 4.2.1.108)
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