3.5.1.103: N-acetyl-1-D-myo-inositol-2-amino-2-deoxy-alpha-D-glucopyranoside deacetylase
This is an abbreviated version!
For detailed information about N-acetyl-1-D-myo-inositol-2-amino-2-deoxy-alpha-D-glucopyranoside deacetylase, go to the full flat file.
Word Map on EC 3.5.1.103
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3.5.1.103
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mycothiol
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mycobacterium
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tuberculosis
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amidase
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actinomycetes
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s-conjugate
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deacetylation
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mycothiol-dependent
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isoniazid
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electrophilic
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low-molecular-weight
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smegmatis
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glcn-ins
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alpha-helices
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antituberculosis
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drug development
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medicine
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analysis
- 3.5.1.103
- mycothiol
- mycobacterium
- tuberculosis
- amidase
- actinomycetes
-
s-conjugate
-
deacetylation
-
mycothiol-dependent
- isoniazid
-
electrophilic
-
low-molecular-weight
- smegmatis
-
glcn-ins
-
alpha-helices
-
antituberculosis
- drug development
- medicine
- analysis
Reaction
Synonyms
1-D-myo-inosityl 2-acetamido-2-deoxy-alpha-D-glucopyranoside deacetylase, 1-D-myo-inosityl 2-N-acetamido-2-deoxy-alpha-D-glucopyranoside deacetylase, 1D-myo-inosityl-2-acetamido-2-deoxy-alpha-D-glucopyranoside deacetylase, AcGI deacetylase, GlcNAc-Ins deacetylase, GlcNAc-Ins-deacetylase, MshB, N-acetyl-1-D-myo-inosityl-2-amino-2-deoxy-alpha-D-glucopyranoside deacetylase, N-acetyl-1-D-myo-inosityl-2-amino-2-deoxy-D-glucopyranoside deacetylase, N-acetyl-1-D-myo-inosityl-2-deoxy-alpha-D-glucopyranoside deacetylase, N-acetylglucosaminylinositol-deacetylase, Rv1170
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Reaction
Reaction on EC 3.5.1.103 - N-acetyl-1-D-myo-inositol-2-amino-2-deoxy-alpha-D-glucopyranoside deacetylase
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1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O = 1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + acetate
1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O = 1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + acetate
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1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O = 1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + acetate
proposed catalytic mechanism: the substrate binds to MshB so that the carbonyl oxygen of the acetyl group replaces the second water molecule on the Zn2+ ion. This leaves the first water molecule in an ideal position for general base-assisted nucleophilic attack of the carbonyl carbon of the acetyl group. The general base is the carboxylate of Asp-15. The tetrahedral transition state would then have a negatively charged oxygen atom that is stabilized by the positively charged Zn2+ and by the imidazolium side chain of His-144. Proton transfer to the nitrogen of the leaving group (GlcN-Ins) would be via the general acid function of the carboxyl group of Asp-15
1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O = 1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + acetate
general acid-base pair mechanism with the side chain of Asp-15 functioning as the general base catalyst and His-144 serving as the general acid catalyst, whereas the side chain of Tyr-142 probably assists in polarizing substrate/stabilizing the oxyanion intermediate. Tyr-142 is a dynamic side chain that plays key roles in catalysis, modulating substrate binding, chemistry, and product release
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1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O = 1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + acetate
proposed catalytic mechanism of MshB, overview. MshB uses a general acid-base mechanism in which Asp15 and His144 act as the general base and acid catalysts respectively, while Tyr142 plays a dynamic role that includes stabilization of the oxyanion intermediate
1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O = 1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + acetate
proposed catalytic mechanism: the substrate binds to MshB so that the carbonyl oxygen of the acetyl group replaces the second water molecule on the Zn2+ ion. This leaves the first water molecule in an ideal position for general base-assisted nucleophilic attack of the carbonyl carbon of the acetyl group. The general base is the carboxylate of Asp-15. The tetrahedral transition state would then have a negatively charged oxygen atom that is stabilized by the positively charged Zn2+ and by the imidazolium side chain of His-144. Proton transfer to the nitrogen of the leaving group (GlcN-Ins) would be via the general acid function of the carboxyl group of Asp-15
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