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Information on EC 3.5.4.1 - cytosine deaminase and Organism(s) Escherichia coli and UniProt Accession P25524
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3.5.4.1 cytosine deaminaseIUBMB Comments
Also acts on 5-methylcytosine.
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Word Map
- 3.5.4.1
- cytidine
- deaminases
- 5-fluorocytosine
-
deamination
-
prodrugs
- virion
-
hypermutation
- viruses
- 5-fluorouracil
-
apolipoprotein
- retroviruses
-
suicide
- uracil
-
retroviral
-
apobecs
-
single-stranded
-
antiretroviral
-
polypeptide-like
-
mrna-editing
-
g-to-a
-
bystander
-
activation-induced
-
retrotransposons
-
anti-hiv-1
-
proviral
-
retroelements
- lentiviruses
-
encapsidation
- ganciclovir
- deoxycytidine
-
retrotransposition
- ssdna
- fiv
- samhd1
-
cullin
-
minus-strand
-
replication-competent
-
gene-directed
- sivmac
- medicine
-
line-1
-
hsv-tk
- vpr
-
gdept
-
non-ltr
- molecular biology
-
xenotropic
- analysis
- pharmacology
- biotechnology
- trim5alpha
- diagnostics
- proviruses
-
nickase
- agriculture
-
single-cycle
-
elongins
The taxonomic range for the selected organisms is: Escherichia coli
The enzyme appears in selected viruses and cellular organisms
The enzyme appears in selected viruses and cellular organisms
Synonyms
apobec3g, apobec3, cytosine deaminase, apobec1, isocytosine deaminase, coda protein, zn2+cdase, fca1p, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
CDase
Cytosine aminohydrolase
-
-
-
-
isocytosine deaminase
-
-
-
-
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cytosine + H2O = uracil + NH3
substrate binding involves a significant conformational change that sequesters the reaction complex from solvent, active site architecture and substrate binding, catalytic mechanism
SYSTEMATIC NAME
IUBMB Comments
cytosine aminohydrolase
Also acts on 5-methylcytosine.
CAS REGISTRY NUMBER
COMMENTARY
9025-05-2
-
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
5-fluorocytosine + H2O
5-fluorouracil + NH3
recombinant fusion enzyme, cytotoxicity could be enhanced by concurrently treating TKglyCD-expressing cells with prodrugs ganclocivir and 5-fluorocytosine, overview
-
-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
used as negative selection marker system, increased 5-fluorocytosine sensitivity in Streptomyces lividans
-
-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
gene-directed enzyme prodrug therapy (GDEPT) with free and liposomal 5-fluorocytosine (5-FC), antitumor effects of liposomal 5-fluorocytosine (5-FC) increased if compared to free prodrug
-
-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
-
-
209493, 209496, 209497, 209502, 209503, 209507, 209508, 667616, 670746, 684772, 685669, 685673, 685848, 685938, 687168, 688280, 688927, 711669, 719155
-
-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
-
recombinant enzyme encoded in an adenoviral vector expressed in murine cancers or human cancer cell lines for prodrug cancer gene therapy, Ad/5HREp-BCD-mediated cytotoxicity under hypoxic conditions, overview
-
-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
-
recombinant enzyme in transfected cells, cytotoxic effects of the enzyme expressed form the AdLPCD vector, overview
-
-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
-
recombinant enzyme, combination of cytosine deaminase with uracil phosphoribosyl transferase leads to local and distant bystander effects against RM1 prostate cancer in mice in gene-directed enzyme prodrug therapy, overview
-
-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
-
activation of the prodrug
-
-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
-
activation of the prodrug to the cytotoxic drug in cancer therapy by recombinant adenoviral vector expressed enzyme in human glioma cells, leads to increased 5-fluorouracil-mediated cell killing, overview
-
-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
activation of the prodrug to the cytotoxic drug in cancer therapy by recombinant enzyme, the cytosine deaminase gene acts as suicide gene leading to increased 5-fluorouracil-mediated murine colorectal cancer cell killing, liposomal formulation of substrate 5-fluorocytosine using dipalmitoylphopshatidylcholine and cholesterol in a 1:1 ratio, overview
-
-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
-
activation of the prodrug to the cytotoxic drug in cancer therapy through the recombinant fusion enzyme cytosine deaminase/uracil phosphoribosyltransferase in human cancer cell lines, overview
-
-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
-
direct inoculation of murine and human brain tumor cell lines, murine neuroblastoma and human glioma cells, with the enzyme transmitted in a recombinant HSV-1 viral oncolytic vector results in cytotoxicity and destruction of cancer cells wth increased cytotoxicity for neighbouring cells, overview
-
-
?
cytosine + H2O
uracil + NH3
-
-
137029, 209484, 209487, 209488, 209489, 209493, 209496, 209497, 209498, 209502, 209503, 209504, 209505, 209506, 209507, 209508, 667616, 670746, 675179, 684772, 685669, 685673, 685848, 685938, 687168, 688280, 688927, 711669, 718902, 719155
-
-
?
cytosine + H2O
uracil + NH3
-
treatment of BDIX rat colon cancer cells using the cytosine deaminase/5-fluorocytosine suicide system induces apoptosis, modulation of the proteome, and Hsp90beta phosphorylation, mechanism of the anticancer effect, overview
-
-
?
additional information
?
-
enzyme is an important member of the pyrimidine salvage pathway
-
-
?
additional information
?
-
-
enzyme is an important member of the pyrimidine salvage pathway
-
-
?
additional information
?
-
-
creatinine is a poor substrate for Zn2+CDase and apoCDase
-
-
?
additional information
?
-
-
adenovirus-mediated hypoxia-targeting cytosine deaminase gene therapy enhances radiotherapy in tumour xenografts of murine tumors, e.g. in human cervical epithelial adenocarcinoma cell line HeLa and human pancreatic carcinoma cell line MIA PaCa-2, as well as in human colon carcinoma cell lines WiDr and HT29, overview
-
-
?
additional information
?
-
-
combination of cytosine deaminase suicide gene expression with treatment with antibody against human death receptor DR5 increases cancer cell cytotoxicity, the death receptors are involved in TNF-related factor-induced apoptosis, overview
-
-
?
additional information
?
-
-
low-dose etoposide enhances telomerase-dependent adenovirus-mediated cytosine deaminase gene therapy through augmentation of adenoviral infection and transgene expression in a syngeneic bladder tumor model, overview
-
-
?
additional information
?
-
-
the enzyme is useful in gene therapy of cancers, conjugation of poly-L-lysine to cytosine deaminase improves the efficacy of enzyme/prodrug cancer therapy, e.g. by a 50times higher cellular uptake than that of control molecules in human breast MDA-MB-231 cancer cells and increase stability after uptake into cells, uptake and intracellular distribution, mechanisms, overview
-
-
?
additional information
?
-
-
the enzyme is useful in treatment of human ovarian cancer by genetic prodrug activation therapy with procaspase-3 co-expression improving the method, overview
-
-
?
NATURAL SUBSTRATE
NATURAL 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
5-fluorocytosine + H2O
5-fluorouracil + NH3
recombinant fusion enzyme, cytotoxicity could be enhanced by concurrently treating TKglyCD-expressing cells with prodrugs ganclocivir and 5-fluorocytosine, overview
-
-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
used as negative selection marker system, increased 5-fluorocytosine sensitivity in Streptomyces lividans
-
-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
-
recombinant enzyme encoded in an adenoviral vector expressed in murine cancers or human cancer cell lines for prodrug cancer gene therapy, Ad/5HREp-BCD-mediated cytotoxicity under hypoxic conditions, overview
-
-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
-
recombinant enzyme in transfected cells, cytotoxic effects of the enzyme expressed form the AdLPCD vector, overview
-
-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
-
recombinant enzyme, combination of cytosine deaminase with uracil phosphoribosyl transferase leads to local and distant bystander effects against RM1 prostate cancer in mice in gene-directed enzyme prodrug therapy, overview
-
-
?
cytosine + H2O
uracil + NH3
-
-
137029, 209484, 209487, 209488, 209489, 209493, 209496, 209497, 209498, 209502, 209503, 209504, 209505, 209506, 209507, 209508, 675179, 684772, 685669, 685673, 685848, 685938, 687168, 688280
-
-
?
cytosine + H2O
uracil + NH3
-
treatment of BDIX rat colon cancer cells using the cytosine deaminase/5-fluorocytosine suicide system induces apoptosis, modulation of the proteome, and Hsp90beta phosphorylation, mechanism of the anticancer effect, overview
-
-
?
additional information
?
-
enzyme is an important member of the pyrimidine salvage pathway
-
-
?
additional information
?
-
-
enzyme is an important member of the pyrimidine salvage pathway
-
-
?
additional information
?
-
-
adenovirus-mediated hypoxia-targeting cytosine deaminase gene therapy enhances radiotherapy in tumour xenografts of murine tumors, e.g. in human cervical epithelial adenocarcinoma cell line HeLa and human pancreatic carcinoma cell line MIA PaCa-2, as well as in human colon carcinoma cell lines WiDr and HT29, overview
-
-
?
additional information
?
-
-
combination of cytosine deaminase suicide gene expression with treatment with antibody against human death receptor DR5 increases cancer cell cytotoxicity, the death receptors are involved in TNF-related factor-induced apoptosis, overview
-
-
?
additional information
?
-
-
low-dose etoposide enhances telomerase-dependent adenovirus-mediated cytosine deaminase gene therapy through augmentation of adenoviral infection and transgene expression in a syngeneic bladder tumor model, overview
-
-
?
additional information
?
-
-
the enzyme is useful in gene therapy of cancers, conjugation of poly-L-lysine to cytosine deaminase improves the efficacy of enzyme/prodrug cancer therapy, e.g. by a 50times higher cellular uptake than that of control molecules in human breast MDA-MB-231 cancer cells and increase stability after uptake into cells, uptake and intracellular distribution, mechanisms, overview
-
-
?
additional information
?
-
-
the enzyme is useful in treatment of human ovarian cancer by genetic prodrug activation therapy with procaspase-3 co-expression improving the method, overview
-
-
?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe2+
bound to the active site, the metal ion coordinates a hydroxyl nucleophile, binding structure, overview
Zn2+
Fe2+
MnCl2
Zn2+
Zn2+
-
bound to the enzyme, below 0.2 mol per mol of subunit, reconstitution of apoenzyme
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
o-phenanthroline
-
removes Fe2+ from the Fe2+CDase to give the apoenzyme, cause of loss in activity, reversible by Fe2+ addition, poor effect on Zn2+CDase
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
conjugation of poly-L-lysine to cytosine deaminase improves the efficacy of enzyme/prodrug cancer therapy, e.g. by a 50times higher cellular uptake than that of control molecules in human breast MDA-MB-231 cancer cells and increase stability after uptake into cells, uptake and intracellular distribution, mechanisms, overview
-
additional information
-
low-dose etoposide enhances telomerase-dependent adenovirus-mediated cytosine deaminase gene therapy through augmentation of adenoviral infection and transgene expression in a syngeneic bladder tumor model, overview
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
3.76
5-fluorocytosine
-
wild type enzyme, pH and temperature not specified in the publication
6.73
5-fluorocytosine
-
mutant enzyme D314E/F316L/D317G, pH and temperature not specified in the publication
7.55
5-fluorocytosine
-
mutant enzyme V315L/F316V/D317G, pH and temperature not specified in the publication
12.69
5-fluorocytosine
-
mutant enzyme V152A/F316C/D317G, pH and temperature not specified in the publication
0.46
cytosine
-
wild type enzyme, pH and temperature not specified in the publication
1.65
cytosine
-
mutant enzyme D314E/F316L/D317G, pH and temperature not specified in the publication
3.16
cytosine
-
mutant enzyme V315L/F316V/D317G, pH and temperature not specified in the publication
4.9
cytosine
-
mutant enzyme V152A/F316C/D317G, pH and temperature not specified in the publication
additional information
additional information
-
pre-steady-state and steady-state kinetics and thermodynamics of cytosine substrate binding to apoenzyme and Zn2+-holoenzyme
-
additional information
additional information
-
the kinetics of the enzyme associated with poly-L-lysine derivatives are very similar to the wild-type enzyme kinetics, overview
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
19.71
5-fluorocytosine
-
wild type enzyme, pH and temperature not specified in the publication
83.68
5-fluorocytosine
-
mutant enzyme D314E/F316L/D317G, pH and temperature not specified in the publication
101.7
5-fluorocytosine
-
mutant enzyme V152A/F316C/D317G, pH and temperature not specified in the publication
115.2
5-fluorocytosine
-
mutant enzyme V315L/F316V/D317G, pH and temperature not specified in the publication
1.69
cytosine
-
mutant enzyme V152A/F316C/D317G, pH and temperature not specified in the publication
2.13
cytosine
-
mutant enzyme D314E/F316L/D317G, pH and temperature not specified in the publication
2.98
cytosine
-
mutant enzyme V315L/F316V/D317G, pH and temperature not specified in the publication
49.68
cytosine
-
wild type enzyme, pH and temperature not specified in the publication
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
5.24
5-fluorocytosine
-
wild type enzyme, pH and temperature not specified in the publication
8.02
5-fluorocytosine
-
mutant enzyme V152A/F316C/D317G, pH and temperature not specified in the publication
12.44
5-fluorocytosine
-
mutant enzyme D314E/F316L/D317G, pH and temperature not specified in the publication
15.27
5-fluorocytosine
-
mutant enzyme V315L/F316V/D317G, pH and temperature not specified in the publication
0.35
cytosine
-
mutant enzyme V152A/F316C/D317G, pH and temperature not specified in the publication
0.94
cytosine
-
mutant enzyme V315L/F316V/D317G, pH and temperature not specified in the publication
1.29
cytosine
-
mutant enzyme D314E/F316L/D317G, pH and temperature not specified in the publication
106.8
cytosine
-
wild type enzyme, pH and temperature not specified in the publication
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
2.6
3.1
87
additional information
additional information
cytosine deaminase of Escherichia coli used as a negative selection marker in Streptomyces, can be applied for any actinobacterial species naturally resistant to 5-fluorocytosine while sensitive to 5-fluorouracil, valuable addition to the actinobacterial genetic toolbox
additional information
-
cytosine deaminase of Escherichia coli used as a negative selection marker in Streptomyces, can be applied for any actinobacterial species naturally resistant to 5-fluorocytosine while sensitive to 5-fluorouracil, valuable addition to the actinobacterial genetic toolbox
additional information
-
incubation of transfected cells increasing concentrations of free or liposomal 5-fluorocytosine (5-FC) for 72 h, effectivness gene-directed enzyme prodrug therapy (GDEPT) tested in mice transplantated with MC-38 tumor cells, survival times of mice bearing tumors, local concentration and toxicity of liposomal prodrug in different organs, enhancement of antitumor effects by liposomal form of 5-fluorocytosine (5-FC)
additional information
incubation of transfected cells increasing concentrations of free or liposomal 5-fluorocytosine (5-FC) for 72 h, effectivness gene-directed enzyme prodrug therapy (GDEPT) tested in mice transplantated with MC-38 tumor cells, survival times of mice bearing tumors, local concentration and toxicity of liposomal prodrug in different organs, enhancement of antitumor effects by liposomal form of 5-fluorocytosine (5-FC)
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
8.5
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
37
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
PDB
SCOP
CATH
UNIPROT
ORGANISM
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
tetramer
additional information
additional information
stabilized by a unique domain-swapping interaction between enzyme subunits, the active site is located in the mouth of the enzyme barrel
additional information
-
stabilized by a unique domain-swapping interaction between enzyme subunits, the active site is located in the mouth of the enzyme barrel
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
10 mg/ml purified recombinant His-tagged enzyme, vapour phase equilibration against 11-14% PEG 8000, 0.1 M HEPES, pH 7.3-7.7, 0.2 M MgCl2, in hanging drop geometry, flash-cooling in a buffer containing 30% v/v glycerol for cryoprotection, also crystallization of a seleno-methionine derivatized enzyme, X-ray diffraction structure determination and analysis at 1.5 A resolution
the structure of Zn-CDA is determined to a resolution of 1.7 A with phosphonocytosine a potent mimic of the putative tetrahedral intermediate bound in the active site
-
the wild type enzyme in complex with the mechanism-based inhibitors 4-(R)-hydroxyl-3,4-dihydropyrimidine or 5-fluoro-4-(S)-hydroxyl-3,4-dihydropyrimidine and the mutant enzyme V152A/F316C/D317G are crystallized by the sitting drop vapor diffusion method, using 10-15% (w/v) PEG 6K, 200 mM MgCl2 and 100 mM HEPES (pH 7-8)
-
wild-type enzyme and mutants D314G, D314A, D314S, free and in complex with mechanism-based inhibitor 5-fluoro-4-(S)-hydroxyl-3,4-dihydropyrimidine
-
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
D314A
PCR-directed mutagenesis, activity against 5-fluorocytosine 2-fold increased, 17-fold lower sensitivity against native cytosine
D134A
-
site-directed mutagenesis, the mutant enzyme shows a higher affinity for cytosine than the wild-type enzyme
D313A
-
metal contet: 0.57 Zn, 0.32 Fe. Mutant possesses less than 0.01% of activity of wild-type enzyme
D313N
-
metal contet: 1.05 Zn, 0.05 Fe. kcat decreased compared to wild-type, Km increased compared to wild-type
D314A
D314E/F316L/D317G
-
the mutant displays 9% substrate specificity towards cytosine and 1820% substrate specificity towards 5-fluorocytosine compared to the wild type enzyme
E217A
-
metal contet: 0.9 Zn, 0.08 Fe. Mutant possesses less than 0.01% of activity of wild-type enzyme
E217Q
-
metal contet: 0.87 Zn, 0.15 Fe. Mutant possesses less than 0.01% of activity of wild-type enzyme
F316A
-
KM-value with cytosine similar to wild-type, decrease in KM-value with 5-fluorocytosine
H246A
-
metal contet: 0.59 Zn, 0.33 Fe. Mutant possesses less than 0.01% of activity of wild-type enzyme
H246N
-
metal contet: 0.53 Zn, 0.29 Fe. Mutant possesses less than 0.01% of activity of wild-type enzyme
H246Q
-
metal contet: 0.31 Zn, 0.33 Fe. kcat and Km decreased compared to wil-type
Q156A
-
metal contet: 0.92 Zn, 0.04 Fe. Mutant possesses less than 0.01% of activity of wild-type enzyme
Q156N
-
metal contet: 1.40 Zn, 0.04 Fe. Mutant possesses less than 0.01% of activity of wild-type enzyme
V152A/F316C/D317G
-
the mutant displays 4% substrate specificity towards cytosine and 1920% substrate specificity towards 5-fluorocytosine compared to the wild type enzyme
V315L/F316V/D317G
-
the mutant displays 6% substrate specificity towards cytosine and 1880% substrate specificity towards 5-fluorocytosine compared to the wild type enzyme
additional information
D314A
-
11fold increase in KM-value with cytosine, decrease in KM-value with 5-fluorocytosine
D314A
-
impaired catalytic efficiency for cytosine, improved catalytic efficiency for 5-fluorocytosine
additional information
construction of a fusion protein HSV-1TKglyCD combining Herpes simplex virus type-1 thymidine kinase, HSV-1TK, and Escherichia coli cytosine deaminase, CD, with screening for the optimal suitable linker peptide, molecular modeling, overview
additional information
-
construction of a fusion protein HSV-1TKglyCD combining Herpes simplex virus type-1 thymidine kinase, HSV-1TK, and Escherichia coli cytosine deaminase, CD, with screening for the optimal suitable linker peptide, molecular modeling, overview
additional information
-
construction of secreted form of enzyme by fusion with pre-prosegment of human tissue plasminogen activator. Secreted enzyme temporarily spares transduced cells and enhanced accumulation of extracellular 5-fluorouracil. Tumors expressing the secreted enzyme have an improved response to 5-fluorocytosine treatment compared to tumors expressing intracellular enzyme
additional information
-
adenovirus-mediated hypoxia-targeting cytosine deaminase gene therapy enhances radiotherapy in tumour xenografts, overview
additional information
-
construction of a chimeric fusion protein consisting of cytosine deaminase and uracil phosphoribosyltransferase in human pancreatic cancer and glioma cell lines, the recombinant fusion enzyme mediates 5-fluorouracil cell killing and leads to growth inhibition of tumor tissue, overview
additional information
-
construction of a fusion gene in an adenoviral vector comprising human telomerase reverse transcriptase promoter, and cytosine deaminase from Escherichia coli
additional information
-
construction of a fusion gene using cytosine deaminase in combination with uracil phosphoribosyl transferase, the product of the suicide gene, CDUPRT, converts the prodrug, 5-fluorocytosine, into 5-fluorouracil and other cytotoxic metabolites that kill both CDUPRT-expressing and surrounding cells, via a bystander effect, in pseudo-metastates in mouse tissues, tissue-specifix effects, overview
additional information
-
construction of a replication-incompetent vector, i.e. AdLPCD vector, comprising the cytosine deaminase gene and the L-plastin promoter, which regulates the expression of transgenes
additional information
-
construction of and transfection with vectors encoding Escherichia coli cytosine deaminase and herpes simplex virus thymidine kinase leads to greater cell death in procaspase-3-expressing clones of 3AO cells, ovarian cancer cells than in control cells after treatment with ganciclovir or 5-fluorocytosine, as well as more rapid activation of caspase-3 and more rapid cleavage of poly (adenosine diphosphate-ribose) polymerase, overview
additional information
-
expression of recombinant cytosine deaminase activity in Bifidobacterium breve I-53-8w is eefective in tumor-targeting enzyme/prodrug therapy in rats, phenotype, overview
additional information
-
expression of recombinant cytosine deaminase activity in Bifidobacterium longum results in and strong enhancement of tumor-targeting enzyme/prodrug therapy in human cells, overview
additional information
-
expression of the enzyme in Rattus norvegicus, BDIX rats, in induced colorectal adenocarcinoma in a gene therapy approach leads to intratumor chemotherapy using 5-fluorocytosine, which is locally converted to 5-fluorouracil, the treatment results in destruction of the gene-modified tumor, other physiological processes might contribute to the tumor destruction, overview
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
60
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
conjugation of poly-L-lysine to cytosine deaminase increases the enzyme's stability after uptake into cells, mechanism, overview
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
5°C, loses 40% of its activity after 2 weeks, lost activity can be restored by treatment with 0.05 mM FeSO4
-
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression of the fusion protein HSV-1TKglyCD in HEK-293 cells and in the human lung cancer cell line NCIH460
plasmid pBCMGSNeo/CD/CMV containing cytosine deaminase of Escherichia coli used for transfection of MC-38 cells
pMP201 vector and derivatives with aminoglycoside resistance gene, synthetic version of the cytosine deaminase gene (CodA), optimized for expression in Streptomyces species, generation of Streptomyces lividans TK24 protoplasts, transformation of Streptomyces lividans
CD gene codA cloned into mammalian expression vector, WiDr cells, a human CRC cell line transformed
-
CDase gene cloned into pBS+ vector, gentically engineered Escherichia coli strain that overexpresses the codBA operon on a multicopy plasmid
-
development of an adenoviral vector for enzyme expression in cancer treatment by gene therapy, expression of the enzyme mutant D134A using this vector in human glioma cell lines D54MG, U87MG, and U251MG
-
expression in human cervical epithelial adenocarcinoma cell line HeLa, human pancreatic carcinoma cell line MIA PaCa-2, and human colon carcinoma cell lines WiDr and HT29
-
expression of a chimeric fusion protein consisting of cytosine deaminase and uracil phosphoribosyltransferase in human pancreatic cancer and glioma cell lines
-
expression of recombinant cytosine deaminase in Bifidobacterium breve I-53-8w using a shuttle plasmid Escherichia coli-Bifidobacterium, overview
-
expression of the enzyme from a replication-incompetent vector, comprising the cytosine deaminase gene and the L-plastin promoter, in human hepatocellular carcinoma cell lines HepG2, Chang Liver, Huh-7 and SK-Hep-1, expression analysis in the different cell lines, overview
-
expression of the enzyme in human and murine cancer cell lines and tumors using a herpes simplex type 1 virus, HSV-1, by exchanging the viral gamma1_34.5 gene for the cytosine deaminase CD gene, method development for the oncolytic HSV vector in gene therapy, overview
-
expression of the enzyme in Rattus norvegicus, BDIX rats, in induced colorectal adenocarcinoma in a gene therapy approach
-
expression of the recombinant fusion gene from adenoviral vector under control of the human telomerase reverse transcriptase promoter in murine syngeneic MBT-2 bladder tumor cells, overview
-
sucloning in strain JM109, construction of a shuttle plasmid Escherichia coli-Bifidobacterium longum, and expression in Bifidobacterium longum strain 105A, expression analysis
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
agriculture
CodA can be used as a negative selection marker in Glycine max. Wild-type seedlings are not affected by inclusion of 5-fluorcytosine in growth media, whiule transgenic Glycine max plants expressing CodA and grown in the presence of more than 200 microg/ml 5-fluorocytosine exhibit reductions in hypocotyl and tap-root lengths, and severe suppression of lateral root development
analysis
in a selection-rooting assay CodA-expressing aerial tissues or shoot cuttings of Glycine max are inhibited for root formation in media containing 5-fluorouracil
medicine
enzyme is of interest both for antimicrobial drug design and for gene therapy applications against tumors
pharmacology
biotechnology
-
a chitosan-entrapped cytosine deaminase nanocomposite is developped. Sustained release of cytosine deaminase from the nanocomposite up to one week depicts its potential implication in prodrug inducted enzyme therapy
medicine
pharmacology
-
exogenous cytosine deaminase gene expression in Bifidobacterium breve I-53-8w for tumor-targeting enzyme/prodrug therapy, overview
pharmacology
the recombinant fusion enzyme HSV-1TKglyCD might be useful in cancer gene therapy
pharmacology
applicability of gene-directed enzyme prodrug therapy (GDEPT), prodrug encapsulation in liposomes, liposomal 5-fluorocytosine (5-FC) achieves high local concentration for suicide therapy
pharmacology
negative selection system for actinobacteria based on cytosine deaminase
medicine
-
oral 5-fluorocytosine in combination with selective delivery of CDase to cancerous cells by selectively introducing the bacterial CDase gene into the genome
medicine
-
gene therapy for treatment of primary and metastatic tumors in the liver, development of gene therapy treatment for metastatic colorectal carcinoma
medicine
-
new approach to chemotherapy of cancer, using substrate 5-fluorocytosine orally and enzyme capsules implanted locally, using conversion of product 5-fluorouracil, a potent antineoplastic substance, which is strongly toxic for mammalian cells as chemotherapeutic tool against tumors, enzyme/prodrug gene therapy, artificial gene composed for metastatic colorectal carcinoma
medicine
-
construction of secreted form of enzyme by fusion with pre-prosegment of human tissue plasminogen activator. Secreted enzyme temporarily spares transduced cells and enhanced accumulation of extracellular 5-fluorouracil. Tumors expressing the secreted enzyme have an improved response to 5-fluorocytosine treatment compared to tumors expressing intracellular enzyme
medicine
-
mutant enzyme with improved activity towards cancer prodrug 5-fluorouracil for suicide gene therapy
medicine
-
establishment of a hypoxia-dependent prodrug-activating system using the enzyme cloned into a hypoxia-targeted adenoviral vector, overview
medicine
-
the enzyme is useful in gene therapy for treatment of cancer, bladder tumor model, overview
medicine
-
the enzyme is useful in gene therapy of cancers, conjugation of poly-L-lysine to cytosine deaminase improves the efficacy of enzyme/prodrug cancer therapy, overview
medicine
-
the enzyme is useful in treatment of human ovarian cancer by genetic prodrug activation therapy, overview
medicine
-
cytosine deaminase is used in combination with 5-fluorocytosine as an enzyme-prodrug combination for targeted genetic cancer treatment
medicine
the cytosine deaminase-human mesenchymal stem cell/5-fluorocytosine system is a potential molecular chemotherapeutic tool for cancer treatment
medicine
-
a Salmonella typhimurium strain overexpressing CodA and resistant to 5-fluorouracyl due to deletion of the Upp gene sequence, after infecting tumour cell cultures, shows increased cytotoxic and bystander effects under standard induction conditions. A PurD mutation in the producer strain controls its intracellular proliferation by the presence of adenine and avoids the intrinsic Salmonella cell death induction
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Sakai, T.; Yu, T.; Omata, S.
Distribution of enzymes related to cytidine degradation in bacteria
Agric. Biol. Chem.
40
1893-1895
1976
Achromobacter liquidum, Achromobacter polymorph, Klebsiella aerogenes, Enterobacter cloacae, Agrobacterium tumefaciens, Alcaligenes faecalis, Alcaligenes viscolactis, Niallia circulans, Bacillus subtilis, Citrobacter freundii, Escherichia coli, Lactiplantibacillus plantarum, Mycobacterium avium, Proteus mirabilis, Proteus vulgaris, Pseudomonas aeruginosa, Pseudomonas putida, Pseudomonas chlororaphis subsp. aureofaciens, Pseudomonas chlororaphis, Pseudomonas cruciviae, Pseudomonas fluorescens, Pseudomonas oleovorans, Pseudomonas schuylkilliensis, Ralstonia solanacearum, Pseudomonas coronafaciens pv. striafaciens, Pseudomonas taetrolens, Pseudomonas trifolii, Serratia marcescens, Serratia polymuthicum, Xanthomonas campestris, Xanthomonas arboricola pv. pruni, Xanthomonas campestris IAM 1671, Enterobacter cloacae IAM 1221, Xanthomonas arboricola pv. pruni IAM 1313, Alcaligenes faecalis IAM 0101, Escherichia coli K12 AKU 0005, Agrobacterium tumefaciens IAM 1526, Agrobacterium tumefaciens AKU 0300, Serratia polymuthicum AKU 0062, Alcaligenes viscolactis IAM 1517, Pseudomonas putida AKU 0820, Achromobacter polymorph AKU 0122
-
Ipata, P.L.; Marmocchi, F.; Magni, G.; Felicioli, R.; Polidoro, G.
Baker's yeast cytosine deaminase. Some enzymic properties and allosteric inhibition by nucleosides and nucleotides
Biochemistry
10
4270-4276
1971
Saccharomyces cerevisiae, Escherichia coli
Sakai, T.; Yu, T.; Tabe, H.; Omata, S.
Purification of cytosine deaminase from Serratia marcescens
Agric. Biol. Chem.
39
1623-1629
1975
Saccharomyces cerevisiae, Escherichia coli, Serratia marcescens
-
Sakai, T.; Yu, T.; Taniguchi, K.; Omata, S.
Purification of cytosine deaminase from Pseudomonas aureofaciens
Agric. Biol. Chem.
39
2015-2020
1975
Klebsiella aerogenes, Enterobacter cloacae, Alcaligenes faecalis, Bacillus subtilis, Saccharomyces cerevisiae, Citrobacter freundii, Escherichia coli, Micrococcus flavus, Proteus mirabilis, Proteus vulgaris, Pseudomonas aeruginosa, Pseudomonas putida, Pseudomonas chlororaphis subsp. aureofaciens, Pseudomonas chlororaphis, Pseudomonas cruciviae, Pseudomonas fluorescens, Pseudomonas fragi, Pseudomonas schuylkilliensis, Ralstonia solanacearum, Pseudomonas coronafaciens pv. striafaciens, Pseudomonas taetrolens, Pseudomonas trifolii, Serratia marcescens, Serratia polymuthicum, Alcaligenes faecalis type S, Serratia marcescens type S, Enterobacter cloacae IAM 1221, Pseudomonas schuylkilliensis type S, Escherichia coli K12 AKU 0005, Pseudomonas chlororaphis type S, Proteus vulgaris type S, Pseudomonas aeruginosa type S, Pseudomonas putida type S, Proteus mirabilis type S, Pseudomonas trifolii type S, Enterobacter cloacae type S, Alcaligenes faecalis AKU 0101, Serratia polymuthicum AKU 0062, Pseudomonas cruciviae type S, Micrococcus flavus AKU 0502, Klebsiella aerogenes type S, Ralstonia solanacearum type S
-
Yu, T.; Sakai, T.; Omata, S.
Kinetic properties of cytosine deaminase from Serratia marcescens
Agric. Biol. Chem.
40
543-549
1976
Saccharomyces cerevisiae, Escherichia coli, Pseudomonas chlororaphis subsp. aureofaciens, Serratia marcescens
-
West, T.P.; Shanley, M.S.; O'Donovan, G.A.
Purification and some properties of cytosine deaminase from Salmonella typhimurium
Biochim. Biophys. Acta
791
251-258
1982
Saccharomyces cerevisiae, Escherichia coli, Salmonella enterica subsp. enterica serovar Typhimurium, Salmonella enterica subsp. enterica serovar Typhimurium HD11-AE2
Katsuragi, T.; Sakai, T.; Tonomura, K.
Affinity chromatography of cytosine deaminase from Escherichia coli with immobilized pyrimidine compounds
Agric. Biol. Chem.
50
1713-1719
1986
Escherichia coli
-
Katsuragi, T.; Sakai, T.; Matsumoto, K.; Tonomura, K.
Cytosine deaminase from Escherichia coli-production, purification and some characteristics
Agric. Biol. Chem.
50
1721-1730
1986
Saccharomyces cerevisiae, Escherichia coli, Pseudomonas chlororaphis subsp. aureofaciens, Salmonella enterica subsp. enterica serovar Typhimurium, Serratia marcescens
-
Kim, J.M.; Shimizu, S.; Yamada, H.
Cytosine deaminase that hydrolyzes creatinine to N-methylhydantoin in various cytosine deaminase-forming microorganisms
Arch. Microbiol.
147
58-63
1987
Escherichia coli, Flavobacterium filamentosum, Proteus mirabilis, Pseudomonas putida, Pseudomonas chlororaphis subsp. aureofaciens, Pseudomonas chlororaphis, Pseudomonas cruciviae, Escherichia coli K12 AKU 0005
-
Austin, E.A.; Huber, B.E.
A first step in the development of gene therapy for colorectal carcinoma: Clonig, sequencing, and expression of Escherichia coli cytosine deaminase
Mol. Pharmacol.
43
380-387
1992
Escherichia coli
Porter, D.J.T.; Austin, E.A.
Cytosine deaminase the roles of divalent metal ions in catalysis
J. Biol. Chem.
268
24005-24011
1993
Escherichia coli
Huber, B.E.; Austin, E.A.; Richards, C.A.; Davis, S.T.; Good, S.S.
Metabolism of 5-fluorocytosine to 5-fluorouracil in human colorectal tumor cells transduced with the cytosine deaminase gene: Significant antitumor effects when only a small percentage of tumor cells express cytosine deaminase
Proc. Natl. Acad. Sci. USA
91
8302-8306
1994
Escherichia coli
Wei, K.; Huber, B.E.
Cytosine deaminase gene as a positive selection marker
J. Biol. Chem.
271
3812-3816
1996
Escherichia coli
Erbs, P.; Exinger, F.; Jund, R.
Characterization of the Saccharomyces cerevisiae FCY1 gene encoding cytosine deaminase and its homologue FCA1 of Candida albicans
Curr. Genet.
31
1-6
1997
Aspergillus fumigatus, Saccharomyces cerevisiae, Candida albicans, Escherichia coli, Salmonella enterica subsp. enterica serovar Typhimurium, Aspergillus fumigatus IFO5840
Yu, T.S.; Kim, J.; Kim, H.S.
Chemical modification of cytosine deaminase from Aspergillus fumigatus
J. Microbiol.
36
39-42
1998
Aspergillus fumigatus, Saccharomyces cerevisiae, Chromobacterium violaceum, Escherichia coli, Pseudomonas chlororaphis subsp. aureofaciens, Salmonella enterica subsp. enterica serovar Typhimurium, Serratia marcescens, Chromobacterium violaceum YK 391
-
Kim, T.H.; Yu, T.S.
Chemical modification of extracellular cytosine deaminase from Chromobacterium violaceum YK 391
J. Microbiol. Biotechnol.
8
581-587
1998
Arthrobacter sp., Aspergillus fumigatus, Paenibacillus polymyxa, Saccharomyces cerevisiae, Chromobacterium violaceum, Escherichia coli, Pseudomonas chlororaphis subsp. aureofaciens, Salmonella enterica subsp. enterica serovar Typhimurium, Serratia marcescens, Chromobacterium violaceum YK 391
-
Porter, D.J.T.
Escherichia coli cytosine deaminase: the kinetics and thermodynamics for binding of cytosine to the apoenzyme and the Zn2+ holoenzyme are similar
Biochim. Biophys. Acta
1476
239-252
2000
Escherichia coli
Ireton, G.C.; McDermott, G.; Black, M.E.; Stoddard, B.L.
The structure of Escherichia coli cytosine deaminase
J. Mol. Biol.
315
687-697
2002
Escherichia coli (P25524), Escherichia coli
Rehemtulla, A.; Hamstra, D.A.; Kievit, E.; Davis, M.A.; Ng, E.Y.; Dornfeld, K.; Lawrence, T.S.
Extracellular expression of cytosine deaminase results in increased 5-FU production for enhanced enzyme/prodrug therapy
Anticancer Res.
24
1393-1399
2004
Escherichia coli
Mahan, S.D.; Ireton, G.C.; Stoddard, B.L.; Black, M.E.
Alanine-scanning mutagenesis reveals a cytosine deaminase mutant with altered substrate preference
Biochemistry
43
8957-8964
2004
Escherichia coli
Mahan, S.D.; Ireton, G.C.; Knoeber, C.; Stoddard, B.L.; Black, M.E.
Random mutagenesis and selection of Escherichia coli cytosine deaminase for cancer gene therapy
Protein Eng. Des. Sel.
17
625-633
2004
Escherichia coli
Khatri, A.; Zhang, B.; Doherty, E.; Chapman, J.; Ow, K.; Pwint, H.; Martiniello-Wilks, R.; Russell, P.J.
Combination of cytosine deaminase with uracil phosphoribosyl transferase leads to local and distant bystander effects against RM1 prostate cancer in mice
J. Gene Med.
8
1086-1096
2006
Escherichia coli
Jung, K.; Kim, S.; Lee, K.; Kim, C.; Chung, I.
Cytotoxic effect of a replication-incompetent adenoviral vector with cytosine deaminase gene driven by L-plastin promoter in hepatocellular carcinoma cells
Arch. Pharm. Res.
30
770-777
2007
Escherichia coli
Zhang, J.; Wang, Z.; Wei, F.; Qiu, W.; Zhang, L.; Huang, Q.
Computational modeling and functional analysis of Herpes simplex virus type-1 thymidine kinase and Escherichia coli cytosine deaminase fusion protein
Biochem. Biophys. Res. Commun.
360
46-50
2007
Escherichia coli (P25524), Escherichia coli
Hidaka, A.; Hamaji, Y.; Sasaki, T.; Taniguchi, S.; Fujimori, M.
Exogenous cytosine deaminase gene expression in Bifidobacterium breve I-53-8w for tumor-targeting enzyme/prodrug therapy
Biosci. Biotechnol. Biochem.
71
2921-2926
2007
Escherichia coli
Hamaji, Y.; Fujimori, M.; Sasaki, T.; Matsuhashi, H.; Matsui-Seki, K.; Shimatani-Shibata, Y.; Kano, Y.; Amano, J.; Taniguchi, S.
Strong enhancement of recombinant cytosine deaminase activity in Bifidobacterium longum for tumor-targeting enzyme/prodrug therapy
Biosci. Biotechnol. Biochem.
71
874-883
2007
Escherichia coli
Liu, J.; Harada, H.; Ogura, M.; Shibata, T.; Hiraoka, M.
Adenovirus-mediated hypoxia-targeting cytosine deaminase gene therapy enhances radiotherapy in tumour xenografts
Br. J. Cancer
96
1871-1878
2007
Escherichia coli
Kaliberov, S.A.; Chiz, S.; Kaliberova, L.N.; Krendelchtchikova, V.; Della Manna, D.; Zhou, T.; Buchsbaum, D.J.
Combination of cytosine deaminase suicide gene expression with DR5 antibody treatment increases cancer cell cytotoxicity
Cancer Gene Ther.
13
203-214
2006
Escherichia coli
Guffey, M.B.; Parker, J.N.; Luckett, W.S.; Gillespie, G.Y.; Meleth, S.; Whitley, R.J.; Markert, J.M.
Engineered herpes simplex virus expressing bacterial cytosine deaminase for experimental therapy of brain tumors
Cancer Gene Ther.
14
45-56
2007
Escherichia coli
Chaszczewska-Markowska, M.; Stebelska, K.; Sikorski, A.; Madej, J.; Opolski, A.; Ugorski, M.
Liposomal formulation of 5-fluorocytosine in suicide gene therapy with cytosine deaminase - for colorectal cancer
Cancer Lett.
262
164-172
2008
Escherichia coli, Escherichia coli (P25524)
Shieh, G.S.; Shiau, A.L.; Yo, Y.T.; Lin, P.R.; Chang, C.C.; Tzai, T.S.; Wu, C.L.
Low-dose etoposide enhances telomerase-dependent adenovirus-mediated cytosine deaminase gene therapy through augmentation of adenoviral infection and transgene expression in a syngeneic bladder tumor model
Cancer Res.
66
9957-9966
2006
Escherichia coli
Kaliberov, S.A.; Markert, J.M.; Gillespie, G.Y.; Krendelchtchikova, V.; Della Manna, D.; Sellers, J.C.; Kaliberova, L.N.; Black, M.E.; Buchsbaum, D.J.
Mutation of Escherichia coli cytosine deaminase significantly enhances molecular chemotherapy of human glioma
Gene Ther.
14
1111-1119
2007
Escherichia coli
Song, Y.; Kong, B.; Ma, D.; Qu, X.; Jiang, S.
Procaspase-3 enhances the in vitro effect of cytosine deaminase-thymidine kinase disuicide gene therapy on human ovarian cancer
Int. J. Gynecol. Cancer
16
156-164
2006
Escherichia coli
Li, C.; Wildes, F.; Winnard, P.; Artemov, D.; Penet, M.F.; Bhujwalla, Z.M.
Conjugation of poly-L-lysine to bacterial cytosine deaminase improves the efficacy of enzyme/prodrug cancer therapy
J. Med. Chem.
51
3572-3582
2008
Escherichia coli
Negroni, L.; Samson, M.; Guigonis, J.M.; Rossi, B.; Pierrefite-Carle, V.; Baudoin, C.
Treatment of colon cancer cells using the cytosine deaminase/5-fluorocytosine suicide system induces apoptosis, modulation of the proteome, and Hsp90beta phosphorylation
Mol. Cancer Ther.
6
2747-2756
2007
Escherichia coli
Dubeau, M.; Ghinet, M.G.; Jacques, P.; Clermont, N.; Beaulieu, C.; Brzezinski, R.
Cytosine deaminase as a negative selection marker for gene disruption and replacement in the genus Streptomyces and other actinobacteria
Appl. Environ. Microbiol.
75
1211-1214
2009
Escherichia coli (P25524), Escherichia coli
Fuchita, M.; Ardiani, A.; Zhao, L.; Serve, K.; Stoddard, B.L.; Black, M.E.
Bacterial cytosine deaminase mutants created by molecular engineering show improved 5-fluorocytosine-mediated cell killing in vitro and in vivo
Cancer Res.
69
4791-4799
2009
Escherichia coli, Escherichia coli GIA39(DE3)
You, M.H.; Kim, W.J.; Shim, W.; Lee, S.R.; Lee, G.; Choi, S.; Kim, D.Y.; Kim, Y.M.; Kim, H.; Han, S.U.
Cytosine deaminase-producing human mesenchymal stem cells mediate an antitumor effect in a mouse xenograft model
J. Gastroenterol. Hepatol.
24
1393-1400
2009
Escherichia coli (Q6Q8Q1)
Hall, R.S.; Fedorov, A.A.; Xu, C.; Fedorov, E.V.; Almo, S.C.; Raushel, F.M.
Three-dimensional structure and catalytic mechanism of cytosine deaminase
Biochemistry
50
5077-5085
2011
Escherichia coli
Yata, V.K.; Ghosh, S.S.
Synthesis and characterization of a novel chitosan based E. coli cytosine deaminase nanocomposite for potential application in prodrug enzyme therapy
Biotechnol. Lett.
33
153-157
2011
Escherichia coli
Manta, B.; Raushel, F.M.; Himo, F.
Reaction mechanism of zinc-dependent cytosine deaminase from Escherichia coli: a quantum-chemical study
J. Phys. Chem. B
118
5644-5652
2014
Escherichia coli (P25524), Escherichia coli
Mesa-Pereira, B.; Medina, C.; Camacho, E.; Flores, A.; Santero, E.
Improved cytotoxic effects of Salmonella-producing cytosine deaminase in tumour cells
Microb. Biotechnol.
8
169-176
2015
Escherichia coli
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