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Literature summary extracted from

  • Maynes, J.T.; Garen, C.; Cherney, M.M.; Newton, G.; Arad, D.; Av-Gay, Y.; Fahey, R.C.; James, M.N.
    The crystal structure of 1-D-myo-inosityl 2-acetamido-2-deoxy-alpha-D-glucopyranoside deacetylase (MshB) from Mycobacterium tuberculosis reveals a zinc hydrolase with a lactate dehydrogenase fold (2003), J. Biol. Chem., 278, 47166-47170.
    View publication on PubMed

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
3.5.1.103 vapor-diffusion method Mycobacterium tuberculosis
3.5.1.103 vapor-diffusion method with a mother liquor consisting of 15% polyethylene glycol 4000, 50 mm Tris-HCl (pH 8.0), 0.1 m Mg(NO3)2, 6% 1,6-hexanediol, and 10% ethylene glycol. A 1:2 ratio of protein solution (6 mg/ml) to mother liquor is mixed and left for vapor equilibration. Triclinic crystals form after approximately 1 week at room temperature Mycobacterium tuberculosis

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
3.5.1.103 Zn2+ metalloprotein, the deacetylase activity is completely dependent on the presence of a divalent metal cation. The Zn2+ is 5 coordinate with 3 residues from MshB (His-13, Asp-16, His-147) and two water molecules Mycobacterium tuberculosis
3.5.1.103 Zn2+ MshB is a Zn2+ metalloprotein, the deacetylase activity is completely dependent on the presence of a divalent metal cation. The Zn2+ is 5 coordinate with 3 residues from MshB (His-13, Asp-16, His-147) and two water molecules Mycobacterium tuberculosis

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3.5.1.103 1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O Mycobacterium tuberculosis key enzyme in mycothiol biosynthesis 1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
-
 ?
3.5.1.103 1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O Mycobacterium tuberculosis H37Rv key enzyme in mycothiol biosynthesis 1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
3.5.1.103 Mycobacterium tuberculosis P9WJN3
-
-
3.5.1.103 Mycobacterium tuberculosis H37Rv P9WJN3
-
-

Reaction

EC Number Reaction Comment Organism Reaction ID
3.5.1.103 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 Mycobacterium tuberculosis
a

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.5.1.103 1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O
-
 Mycobacterium tuberculosis 1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
-
 ?
3.5.1.103 1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O key enzyme in mycothiol biosynthesis Mycobacterium tuberculosis 1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
-
 ?
3.5.1.103 1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O
-
 Mycobacterium tuberculosis H37Rv 1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
-
 ?
3.5.1.103 1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O key enzyme in mycothiol biosynthesis Mycobacterium tuberculosis H37Rv 1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.5.1.103 1-D-myo-inosityl 2-acetamido-2-deoxy-alpha-D-glucopyranoside deacetylase
-
 Mycobacterium tuberculosis
3.5.1.103 MshB
-
 Mycobacterium tuberculosis