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Literature summary for 3.5.1.103 extracted from

  • Lamprecht, D.A.; Muneri, N.O.; Eastwood, H.; Naidoo, K.J.; Strauss, E.; Jardine, A.
    An enzyme-initiated Smiles rearrangement enables the development of an assay of MshB, the GlcNAc-Ins deacetylase of mycothiol biosynthesis (2012), Org. Biomol. Chem., 10, 5278-5288.
    View publication on PubMed

Metals/Ions

Metals/Ions Comment Organism Structure
Fe2+ the active site metal ion is coordinated to two histidine residues, His13 and His147, and an aspartate, Asp16 Mycobacterium tuberculosis
Zn2+ the active site metal ion is coordinated to two histidine residues, His13 and His147, and an aspartate, Asp16 Mycobacterium tuberculosis

Organism

Organism UniProt Comment Textmining
Mycobacterium tuberculosis P9WJN3
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Reaction

Reaction Comment Organism Reaction ID
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 Mycobacterium tuberculosis

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
additional information 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 Mycobacterium tuberculosis ?
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N-acetyl-1-D-myo-inosityl-2-amino-2-deoxy-D-glucopyranoside + H2O molecular docking analysis of the MshB active site binding pocket, overview Mycobacterium tuberculosis 1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + acetate
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N-acetyl-D-glucosamine + H2O commercially available alternate minimal substrate, MshB is 100fold less active towards this compound than toward the natural substrate Mycobacterium tuberculosis acetate + D-glucosamine
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Synonyms

Synonyms Comment Organism
GlcNAc-Ins deacetylase
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Mycobacterium tuberculosis
MshB
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Mycobacterium tuberculosis
N-acetyl-1-D-myo-inosityl-2-amino-2-deoxy-D-glucopyranoside deacetylase
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Mycobacterium tuberculosis

General Information

General Information Comment Organism
metabolism the enzyme is involved in the biosynthesis of mycothiol (MSH), a protective low molecular weight thiol present only in Mycobacterium tuberculosis and other actinomycetes Mycobacterium tuberculosis