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Literature summary extracted from

  • Gammon, D.W.; Steenkamp, D.J.; Mavumengwana, V.; Marakalala, M.J.; Mudzunga, T.T.; Hunter, R.; Munyololo, M.
    Conjugates of plumbagin and phenyl-2-amino-1-thioglucoside inhibit MshB, a deacetylase involved in the biosynthesis of mycothiol (2010), Bioorg. Med. Chem., 18, 2501-2514.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.5.1.103 benzyl 2-deoxy-2-acetamido-1-thio-beta-D-glucopyranoside 0.5 mM, 13% inhibition Mycobacterium tuberculosis
3.5.1.103 cyclohexyl (2''R),(2''S)-3,3''-anhydro-2-deoxy-2-C-(2'',3''-dihydroxypropyl)-alpha-D-glucopyranoside 0.5 mM, 6.6% inhibition Mycobacterium tuberculosis
3.5.1.103 cyclohexyl 2-deoxy-2-C-(2'',3''-epoxypropyl)-alpha-D-glucopyranoside 0.5 mM, 19.7% inhibition Mycobacterium tuberculosis
3.5.1.103 cyclohexyl 2-deoxy-2-C-(2''-hydroxypropyl)-alpha-D-glucopyranoside 0.5 mM, 11.4% inhibition Mycobacterium tuberculosis
3.5.1.103 cyclohexyl 2-deoxy-2-C-(2''-oxopropyl)-a-D-glucopyranoside 0.5 mM, 6.7% inhibition Mycobacterium tuberculosis
3.5.1.103 cyclohexyl-2-chloroacetamido-2-deoxy-1-thio-alpha-D-glucopyranoside 0.5 mM, 15% inhibition Mycobacterium tuberculosis
3.5.1.103 phenyl-2-acetamido-2-deoxy-1-thio-alpha-D-glucopyranoside 0.5 mM, 6% inhibition Mycobacterium tuberculosis
3.5.1.103 phenyl-2-deoxy-2-acetamido-1-thio-beta-D-glucopyranoside 0.5 mM, 15% inhibition Mycobacterium tuberculosis
3.5.1.103 phenyl-2-deoxy-2-[3'-(8''-hydroxy-3''-methyl-1'',4''-dioxo-1'',4''-dihydronaphthalen-2''-yl)butanamido]-1-thio-alpha-D-glucopyranoside 0.5 mM, 81.6% inhibition Mycobacterium tuberculosis
3.5.1.103 phenyl-2-deoxy-2-[3'-(8''-hydroxy-3''-methyl-1'',4''-dioxo-1'',4''-dihydronaphthalen-2''-yl)pentanamido]-1-thio-alpha-D-glucopyranoside 0.5 mM, 81.4% inhibition Mycobacterium tuberculosis
3.5.1.103 phenyl-2-deoxy-2-[3'-(8''-hydroxy-3''-methyl-1'',4''-dioxo-1'',4''-dihydronaphthalen-2''-yl)propanamido]-1-thio-alpha-D-glucopyranoside 0.5 mM, 57.4% inhibition Mycobacterium tuberculosis

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
3.5.1.103 0.348
-
 1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol pH 7.5, 37°C Mycobacterium tuberculosis
3.5.1.103 1.695
-
 phenyl-2-acetamido-2-deoxy-1-thio-alpha-D-glucopyranoside
-
 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 biosynthesis of mycothiol and detoxification of xenobiotics as their mycothiol-S-conjugates 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
-
-
-

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 biosynthesis of mycothiol and detoxification of xenobiotics as their mycothiol-S-conjugates Mycobacterium tuberculosis 1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate
-
 ?
3.5.1.103 cyclohexyl-2-acetamido-2-deoxy-1-thio-alpha-D-glucopyranoside + H2O 6% of the activity with 1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol Mycobacterium tuberculosis cyclohexyl-2-amino-2-deoxy-1-thio-alpha-D-glucopyranoside + acetate
-
 ?
3.5.1.103 cyclohexyl-2-acetamido-2-deoxy-alpha-D-glucopyranoside + H2O 6% of the activity with 1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol Mycobacterium tuberculosis cyclohexyl-2-amino-2-deoxy-alpha-D-glucopyranoside + acetate
-
 ?
3.5.1.103 phenyl 2-acetamido-2-deoxy-1-thio-alpha-D-glucopyranoside + H2O
-
 Mycobacterium tuberculosis phenyl 2-amino-2-deoxy-1-thio-alpha-D-glucopyranoside + acetate
-
 ?
3.5.1.103 phenyl 2-acetamido-2-deoxy-1-thio-alpha-D-glucopyranoside + H2O 25% of the activity with 1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol Mycobacterium tuberculosis phenyl 2-amino-2-deoxy-1-thio-alpha-D-glucopyranoside + acetate
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.5.1.103 GlcNAc-Ins-deacetylase
-
 Mycobacterium tuberculosis
3.5.1.103 MshB
-
 Mycobacterium tuberculosis
3.5.1.103 N-acetylglucosaminylinositol-deacetylase
-
 Mycobacterium tuberculosis

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
3.5.1.103 37
-
 assay at Mycobacterium tuberculosis

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
3.5.1.103 0.12
-
 phenyl-2-acetamido-2-deoxy-1-thio-alpha-D-glucopyranoside pH 7.5, 37°C Mycobacterium tuberculosis
3.5.1.103 0.24
-
 1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol pH 7.5, 37°C Mycobacterium tuberculosis

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
3.5.1.103 7.5
-
 assay at Mycobacterium tuberculosis

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
3.5.1.103 0.07
-
 phenyl-2-acetamido-2-deoxy-1-thio-alpha-D-glucopyranoside pH 7.5, 37°C Mycobacterium tuberculosis
3.5.1.103 0.68
-
 1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol pH 7.5, 37°C Mycobacterium tuberculosis