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
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s-conjugate
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deacetylation
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mycothiol-dependent
- isoniazid
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electrophilic
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low-molecular-weight
- smegmatis
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glcn-ins
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alpha-helices
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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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Substrates Products
Substrates Products on EC 3.5.1.103 - N-acetyl-1-D-myo-inositol-2-amino-2-deoxy-alpha-D-glucopyranoside deacetylase
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REACTION DIAGRAM
1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O
1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
1-D-myo-inosityl-2-acetamido-2-deoxy-alpha-D-glucopyranoside + H2O
1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
key enzyme in mycothiol biosynthesis. Mycothiol is the major low molecular weight thiol in actinomycetes and is essential for growth of Mycobacterium tuberculosis
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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)-D-myo-inositol + H2O
1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-D-myo-inositol + acetate
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cyclohexyl-2-acetamido-2-deoxy-1-thio-alpha-D-glucopyranoside + H2O
cyclohexyl-2-amino-2-deoxy-1-thio-alpha-D-glucopyranoside + acetate
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6% of the activity with 1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol
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cyclohexyl-2-acetamido-2-deoxy-alpha-D-glucopyranoside + H2O
cyclohexyl-2-amino-2-deoxy-alpha-D-glucopyranoside + acetate
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6% of the activity with 1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol
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N-acetyl-1-D-myo-inosityl-2-amino-2-deoxy-alpha-D-glucopyranoside + H2O
1-D-myo-inosityl-2-amino-2-deoxy-alpha-D-glucopyranoside + acetate
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N-acetyl-1-D-myo-inosityl-2-amino-2-deoxy-D-glucopyranoside + H2O
1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + acetate
molecular docking analysis of the MshB active site binding pocket, overview
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N-acetyl-1D-myo-inosityl-2-amino-2-deoxy-alpha-D-glucopyranoside + H2O
1D-myo-inosityl-2-amino-2-deoxy-alpha-D-glucopyranoside + acetate
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N-deacetyl-N-formylmycothiol-monobromobimane conjugate + H2O
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phenyl 2-acetamido-2-deoxy-1-thio-alpha-D-glucopyranoside + H2O
phenyl 2-amino-2-deoxy-1-thio-alpha-D-glucopyranoside + acetate
1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
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1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O
1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
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?
1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O
1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
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?
1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O
1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
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?
1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O
1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
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?
1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O
1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
biosynthesis of mycothiol
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1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O
1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
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biosynthesis of mycothiol and detoxification of xenobiotics as their mycothiol-S-conjugates
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1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O
1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
key enzyme in mycothiol biosynthesis
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?
1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O
1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
mycothiol biosynthesis
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?
1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O
1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
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mycothiol biosynthesis
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?
1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O
1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
step in mycothiol biosynthesis
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1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O
1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
activity with 1-D-myo-inosityl-2-acetamido-2-deoxy-alpha-D-glucopyranoside as the substrate is over 300fold greater than the deacetylase activity determined with N-acety-D-glucosamine and 23fold greater than the amidase activity measured with MSmB
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1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O
1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
the enzyme is specific for 1-D-myo-inosityl 2-N-acetamido-2-deoxy-alpha-D-glucopyranoside
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1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O
1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
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1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O
1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
step in mycothiol biosynthesis
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1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O
1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
biosynthesis of mycothiol
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1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O
1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
the enzyme is specific for 1-D-myo-inosityl 2-N-acetamido-2-deoxy-alpha-D-glucopyranoside
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1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O
1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
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1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O
1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
mycothiol biosynthesis
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1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O
1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
activity with 1-D-myo-inosityl-2-acetamido-2-deoxy-alpha-D-glucopyranoside as the substrate is over 300fold greater than the deacetylase activity determined with N-acety-D-glucosamine and 23fold greater than the amidase activity measured with MSmB
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1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O
1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
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1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O
1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
key enzyme in mycothiol biosynthesis
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1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O
1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
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1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O
1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
mycothiol biosynthesis
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1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O
1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
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the inositol moiety primarily contributes to the affinity of N-acetyl-1-D-myo-inosityl-2-amino-2-deoxy-alpha-D-glucopyranoside for MshB
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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
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acetate + D-glucosamine
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N-acetyl-D-glucosamine + H2O
acetate + D-glucosamine
commercially available alternate minimal substrate, MshB is 100fold less active towards this compound than toward the natural substrate
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N-acetyl-D-glucosamine + H2O
acetate + D-glucosamine
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D-glucosamine + acetate
activity is 300fold lower than with 1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol
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N-acetyl-D-glucosamine + H2O
D-glucosamine + acetate
activity is 73fold lower than with 1-D-myo-inosityl-2-acetamido-2-deoxy-alpha-D-glucopyranoside
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N-acetyl-D-glucosamine + H2O
D-glucosamine + acetate
activity is 300fold lower than with 1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol
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N-acetyl-D-glucosamine + H2O
D-glucosamine + acetate
activity is 73fold lower than with 1-D-myo-inosityl-2-acetamido-2-deoxy-alpha-D-glucopyranoside
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N-acetyl-D-glucosamine + H2O
D-glucosamine + acetate
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phenyl 2-amino-2-deoxy-1-thio-alpha-D-glucopyranoside + acetate
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phenyl 2-acetamido-2-deoxy-1-thio-alpha-D-glucopyranoside + H2O
phenyl 2-amino-2-deoxy-1-thio-alpha-D-glucopyranoside + acetate
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25% of the activity with 1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol
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MshB shows amidase activity with a wide range of substrates
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additional information
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MshB shows amidase activity with a wide range of substrates
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additional information
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the enzyme is unable to remove the acetyl residue from the acetylcysteinyl group of mycothiol or S-(2-oxo-2-phenylethyl)mycothiol, and it exhibits barely detectable amidase activity with mycothiol or mycothiol disulfide. It has significant amidase activity with S-(2-oxo-2-phenylethyl)mycothiol and even greater activity with N-deacetyl-N-formylmycothiol-monobromobimane conjugate, N-deacetyl-mycothiol-monobromobimane conjugate, formyl-CySmB-GlcN-Ins, and mycothiol-monobromobimane conjugate
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additional information
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the enzyme is unable to remove the acetyl residue from the acetylcysteinyl group of mycothiol or S-(2-oxo-2-phenylethyl)mycothiol, and it exhibits barely detectable amidase activity with mycothiol or mycothiol disulfide. It has significant amidase activity with S-(2-oxo-2-phenylethyl)mycothiol and even greater activity with N-deacetyl-N-formylmycothiol-monobromobimane conjugate, N-deacetyl-mycothiol-monobromobimane conjugate, formyl-CySmB-GlcN-Ins, and mycothiol-monobromobimane conjugate
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additional information
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molecular determinants of MshB substrate specificity, docking analysis and simulations, a hydrophobic cavity adjacent to the active site may be one important determinant of MshB substrate specificity, the side chains of Asp15, His144, Asp146 and Tyr142 are important contributors to MshB catalytic activity, and Tyr142 appears to be a dynamic side chain that participates throughout the catalytic cycle, participating in substrate binding, chemistry, and product release
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additional information
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structural analogues of N-acetyl-1-D-myo-inosityl-2-amino-2-deoxy-D-glucopyranoside in which the inosityl moiety is replaced by a chromophore are synthesized and evaluated as alternate substrates of MshB, assay method optimization for high-throughput measurements, molecular docking analysis of the MshB active site binding pocke, overview
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additional information
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structural analogues of N-acetyl-1-D-myo-inosityl-2-amino-2-deoxy-D-glucopyranoside in which the inosityl moiety is replaced by a chromophore are synthesized and evaluated as alternate substrates of MshB, assay method optimization for high-throughput measurements, molecular docking analysis of the MshB active site binding pocke, overview
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additional information
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MshB shows amidase activity with a wide range of substrates
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additional information
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the enzyme is unable to remove the acetyl residue from the acetylcysteinyl group of mycothiol or S-(2-oxo-2-phenylethyl)mycothiol, and it exhibits barely detectable amidase activity with mycothiol or mycothiol disulfide. It has significant amidase activity with S-(2-oxo-2-phenylethyl)mycothiol and even greater activity with N-deacetyl-N-formylmycothiol-monobromobimane conjugate, N-deacetyl-mycothiol-monobromobimane conjugate, formyl-CySmB-GlcN-Ins, and mycothiol-monobromobimane conjugate
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additional information
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MshB activity as a control point regulating mycothiol production
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additional information
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MshB activity as a control point regulating mycothiol production
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additional information
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Mycolicibacterium smegmatis mc(2)155 / ATCC 700084
MshB activity as a control point regulating mycothiol production
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