BRENDA - Enzyme Database show
show all sequences of 4.1.3.36

Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis

Li, X.; Liu, N.; Zhang, H.; Knudson, S.E.; Slayden, R.A.; Tonge, P.J.; Bioorg. Med. Chem. Lett. 20, 6306-6309 (2010)

Data extracted from this reference:

Cloned(Commentary)
Commentary
Organism
-
Mycobacterium tuberculosis
Inhibitors
Inhibitors
Commentary
Organism
Structure
(3Z)-3-(3,3-dimethyl-2-oxobutylidene)-3,4-dihydro-2H-1,4-benzoxazin-2-one
68.4% inhibition at 0.125 mg/ml, 0.00015 mM o-succinylbenzoate , pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
(3Z)-3-(3,3-dimethyl-2-oxobutylidene)-6-(ethylsulfonyl)-3,4-dihydro-2H-1,4-benzoxazin-2-one
60.3% inhibition at 0.125 mg/ml, 0.00015 mM o-succinylbenzoate, pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
(3Z)-6-chloro-3-(4-methyl-2-oxopentylidene)-3,4-dihydro-2H-1,4-benzoxazin-2-one
98% inhibition at 0.125 mg/ml, 0.00015 mM o-succinylbenzoate, pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
(3Z)-6-methyl-3-(4-methyl-2-oxopentylidene)-3,4-dihydro-2H-1,4-benzoxazin-2-one
77.3% inhibition at 0.125 mg/ml, 0.00015 mM o-succinylbenzoate, pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
methyl (2Z)-(2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
Mycobacterium tuberculosis
methyl (2Z)-(5-methyl-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
Mycobacterium tuberculosis
methyl (2Z)-(6-chloro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
Mycobacterium tuberculosis
methyl (2Z)-(6-fluoro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
Mycobacterium tuberculosis
methyl (2Z)-(6-methyl-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
Mycobacterium tuberculosis
methyl (2Z)-(6-nitro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
Mycobacterium tuberculosis
methyl (2Z)-(7-chloro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
Mycobacterium tuberculosis
methyl (2Z)-(7-fluoro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
Mycobacterium tuberculosis
methyl (2Z)-(7-methyl-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
Mycobacterium tuberculosis
methyl (2Z)-(7-nitro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
Mycobacterium tuberculosis
methyl (2Z)-[6-(ethylsulfonyl)-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene]ethanoate
-
Mycobacterium tuberculosis
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Mycobacterium tuberculosis
-
-
-
Purification (Commentary)
Commentary
Organism
-
Mycobacterium tuberculosis
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
o-succinylbenzoyl-CoA
-
714417
Mycobacterium tuberculosis
1,4-dihydroxy-2-naphthoyl-CoA + H2O + H2O
-
-
-
?
Subunits
Subunits
Commentary
Organism
hexamer
-
Mycobacterium tuberculosis
Ki Value [mM]
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
0.0091
-
methyl (2Z)-(2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
non-competitive inhibitor, pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
0.0115
-
methyl (2Z)-(6-fluoro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
non-competitive inhibitor , pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
0.0225
-
methyl (2Z)-(6-chloro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
non-competitive inhibitor, pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
IC50 Value
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
0.01
-
non-competitive inhibitor Ki' = 0.067 mM, pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
methyl (2Z)-(2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
0.0179
-
pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
methyl (2Z)-[6-(ethylsulfonyl)-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene]ethanoate
0.0182
-
pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
methyl (2Z)-(7-methyl-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
0.0203
-
pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
methyl (2Z)-(7-nitro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
0.0231
-
pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
methyl (2Z)-(6-methyl-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
0.0241
-
pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
methyl (2Z)-(5-methyl-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
0.027
-
non-competitive inhibitor Ki' = 0.0101 mM, pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
methyl (2Z)-(6-fluoro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
0.0282
-
pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
methyl (2Z)-(6-nitro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
0.03
-
pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
methyl (2Z)-(7-fluoro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
0.0357
-
pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
methyl (2Z)-(7-chloro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
0.0463
-
non-competitive inhibitor Ki' = 0.0185 mM, pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
methyl (2Z)-(6-chloro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
Cloned(Commentary) (protein specific)
Commentary
Organism
-
Mycobacterium tuberculosis
IC50 Value (protein specific)
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
0.01
-
non-competitive inhibitor Ki' = 0.067 mM, pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
methyl (2Z)-(2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
0.0179
-
pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
methyl (2Z)-[6-(ethylsulfonyl)-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene]ethanoate
0.0182
-
pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
methyl (2Z)-(7-methyl-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
0.0203
-
pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
methyl (2Z)-(7-nitro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
0.0231
-
pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
methyl (2Z)-(6-methyl-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
0.0241
-
pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
methyl (2Z)-(5-methyl-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
0.027
-
non-competitive inhibitor Ki' = 0.0101 mM, pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
methyl (2Z)-(6-fluoro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
0.0282
-
pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
methyl (2Z)-(6-nitro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
0.03
-
pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
methyl (2Z)-(7-fluoro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
0.0357
-
pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
methyl (2Z)-(7-chloro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
0.0463
-
non-competitive inhibitor Ki' = 0.0185 mM, pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
methyl (2Z)-(6-chloro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
(3Z)-3-(3,3-dimethyl-2-oxobutylidene)-3,4-dihydro-2H-1,4-benzoxazin-2-one
68.4% inhibition at 0.125 mg/ml, 0.00015 mM o-succinylbenzoate , pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
(3Z)-3-(3,3-dimethyl-2-oxobutylidene)-6-(ethylsulfonyl)-3,4-dihydro-2H-1,4-benzoxazin-2-one
60.3% inhibition at 0.125 mg/ml, 0.00015 mM o-succinylbenzoate, pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
(3Z)-6-chloro-3-(4-methyl-2-oxopentylidene)-3,4-dihydro-2H-1,4-benzoxazin-2-one
98% inhibition at 0.125 mg/ml, 0.00015 mM o-succinylbenzoate, pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
(3Z)-6-methyl-3-(4-methyl-2-oxopentylidene)-3,4-dihydro-2H-1,4-benzoxazin-2-one
77.3% inhibition at 0.125 mg/ml, 0.00015 mM o-succinylbenzoate, pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
methyl (2Z)-(2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
Mycobacterium tuberculosis
methyl (2Z)-(5-methyl-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
Mycobacterium tuberculosis
methyl (2Z)-(6-chloro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
Mycobacterium tuberculosis
methyl (2Z)-(6-fluoro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
Mycobacterium tuberculosis
methyl (2Z)-(6-methyl-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
Mycobacterium tuberculosis
methyl (2Z)-(6-nitro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
Mycobacterium tuberculosis
methyl (2Z)-(7-chloro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
Mycobacterium tuberculosis
methyl (2Z)-(7-fluoro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
Mycobacterium tuberculosis
methyl (2Z)-(7-methyl-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
Mycobacterium tuberculosis
methyl (2Z)-(7-nitro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
Mycobacterium tuberculosis
methyl (2Z)-[6-(ethylsulfonyl)-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene]ethanoate
-
Mycobacterium tuberculosis
Ki Value [mM] (protein specific)
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
0.0091
-
methyl (2Z)-(2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
non-competitive inhibitor, pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
0.0115
-
methyl (2Z)-(6-fluoro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
non-competitive inhibitor , pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
0.0225
-
methyl (2Z)-(6-chloro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
non-competitive inhibitor, pH not specified in the publication, temperature not specified in the publication
Mycobacterium tuberculosis
Purification (Commentary) (protein specific)
Commentary
Organism
-
Mycobacterium tuberculosis
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
o-succinylbenzoyl-CoA
-
714417
Mycobacterium tuberculosis
1,4-dihydroxy-2-naphthoyl-CoA + H2O + H2O
-
-
-
?
Subunits (protein specific)
Subunits
Commentary
Organism
hexamer
-
Mycobacterium tuberculosis
Other publictions for EC 4.1.3.36
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Temperature Optimum [°C]
Temperature Range [°C]
Temperature Stability [°C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [°C] (protein specific)
Temperature Range [°C] (protein specific)
Temperature Stability [°C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
748290
Passi
RepTB a gene ontology based d ...
Mycobacterium tuberculosis
J. Cheminform.
10
24
2018
-
-
-
-
-
-
12
-
-
-
-
1
-
1
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
12
-
-
-
-
-
1
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
746618
Song
Ligand-dependent active-site ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv
Acta Crystallogr. Sect. D
70
2959-2969
2014
-
-
1
1
-
-
-
-
-
-
-
2
-
4
-
-
1
-
-
-
-
-
2
1
-
-
-
-
-
-
-
1
-
-
-
-
-
1
1
1
-
-
-
-
-
-
-
-
-
2
-
-
-
1
-
-
-
-
2
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
728604
Sun
Structural basis of the induce ...
Escherichia coli, Synechocystis sp.
PLoS ONE
8
e63095
2013
-
-
2
2
4
-
4
4
-
-
-
2
-
4
-
-
2
2
-
-
-
-
4
-
-
-
-
4
2
-
-
-
-
-
-
-
-
2
-
2
4
-
-
4
-
4
-
-
-
2
-
-
-
2
-
-
-
-
4
-
-
-
-
4
2
-
-
-
-
3
3
-
4
4
726985
Sun
Active site binding and cataly ...
Escherichia coli, Synechocystis sp.
Biochemistry
51
4580-4589
2012
-
-
2
2
-
-
-
-
-
2
-
2
-
2
-
-
2
2
-
-
-
-
2
-
-
-
-
-
2
-
-
-
-
-
-
-
-
2
-
2
-
-
-
-
-
-
-
2
-
2
-
-
-
2
-
-
-
-
2
-
-
-
-
-
2
-
-
-
-
6
6
-
-
-
714260
Chen
Stabilization of the second ox ...
Escherichia coli
Biochemistry
50
5893-5904
2011
-
-
1
-
8
-
4
-
-
-
-
-
-
3
-
-
1
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
4
-
-
-
-
1
-
-
8
-
-
4
4
-
-
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-
-
-
-
-
1
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
714273
Li
Mechanism of the intramolecula ...
Escherichia coli, Mycobacterium tuberculosis
Biochemistry
50
9532-9544
2011
-
-
2
2
8
-
-
6
-
-
1
-
-
4
-
-
2
-
-
-
-
-
3
2
-
-
-
6
-
-
-
-
-
-
-
-
-
2
-
2
8
-
-
-
-
6
-
-
1
-
-
-
-
2
-
-
-
-
3
2
-
-
-
6
-
-
-
-
-
-
-
-
6
6
726554
Li
CoA adducts of 4-oxo-4-phenylb ...
Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv
ACS Med. Chem. Lett.
2
818-823
2011
-
1
-
-
-
-
20
-
-
-
-
-
-
4
-
-
-
-
-
-
-
-
2
-
1
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-
-
1
-
-
-
3
-
18
-
1
-
-
-
-
-
18
20
3
-
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-
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-
-
2
-
1
-
-
-
1
-
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-
-
-
-
-
-
704888
Babujee
The proteome map of spinach le ...
Spinacia oleracea
J. Exp. Bot.
61
1441-1453
2010
-
-
-
-
-
-
-
-
1
-
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1
-
6
-
-
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-
1
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1
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1
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1
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1
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1
-
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-
-
-
-
-
-
-
-
-
-
-
-
-
714417
Li
Synthesis and SAR studies of 1 ...
Mycobacterium tuberculosis
Bioorg. Med. Chem. Lett.
20
6306-6309
2010
-
-
1
-
-
-
15
-
-
-
-
-
-
3
-
-
1
-
-
-
-
-
1
1
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-
-
-
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-
-
-
3
-
11
-
-
1
-
-
-
-
11
15
3
-
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-
-
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-
-
-
1
-
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-
-
1
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
690466
Lannergard
Identification of the genetic ...
Staphylococcus aureus
Antimicrob. Agents Chemother.
52
4017-4022
2008
-
1
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1
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4
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1
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1
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1
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1
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-
-
677366
Kanaujia
Cloning, expression, purificat ...
Geobacillus kaustophilus
Acta Crystallogr. Sect. F
63
103-105
2007
-
-
1
1
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-
-
-
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1
-
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4
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1
-
-
-
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1
1
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1
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1
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1
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1
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1
1
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663500
Johnston
Structure of naphthoate syntha ...
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Kolkmann
4-(2'-Carboxyphenyl)-4-oxobuty ...
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Shaw
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Recombinent plasmids containin ...
Escherichia coli
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Heide
Enzymatic synthesis, character ...
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Heide
Enzymatic synthesis of the coe ...
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93958
Meganathan
Menaquinone (vitamin K2) biosy ...
Mycolicibacterium phlei
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1979
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