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Literature summary extracted from

  • Patel, K.; Song, F.; Andreana, P.R.
    Synthesis of substrate analogues as potential inhibitors for Mycobacterium tuberculosis enzyme MshC (2017), Carbohydr. Res., 453-454, 10-18 .
    View publication on PubMed

Application

EC Number Application Comment Organism
6.3.1.13 drug development mycothiol cysteine ligase (MshC) is a promising target for developing anti-mycobacterial compounds Mycobacterium tuberculosis

Inhibitors

EC Number Inhibitors Comment Organism Structure
6.3.1.13 1,3,4,6-tetra-O-acetyl-2-deoxy-2-azido-D-glucopyranose
-
 Mycobacterium tuberculosis
6.3.1.13 1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-alpha-D-mannopyranose
-
 Mycobacterium tuberculosis
6.3.1.13 1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-D-glucopyranose
-
 Mycobacterium tuberculosis
6.3.1.13 1-D-myo-inositol 2-azido-2-deoxy-alpha-D-glucopyranoside
-
 Mycobacterium tuberculosis
6.3.1.13 1-D-myo-inositol 2-fluoro-2-deoxy-alpha-D-glucopyranoside
-
 Mycobacterium tuberculosis
6.3.1.13 2,3:4,5-di-O-cyclohexylidene-(1R)-menthyloxycarbonyl-D-myo-inositol
-
 Mycobacterium tuberculosis
6.3.1.13 2,3:4,5-di-O-cyclohexylidene-D-myo-inositol
-
 Mycobacterium tuberculosis
6.3.1.13 3,4,6-tri-O-acetyl-2-deoxy-2-azido-D-glucopyranose
-
 Mycobacterium tuberculosis
6.3.1.13 3,4,6-tri-O-acetyl-2-deoxy-2-azido-D-glucopyranosyl trichloroacetimidate
-
 Mycobacterium tuberculosis
6.3.1.13 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-D-glucopyranose
-
 Mycobacterium tuberculosis
6.3.1.13 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-D-glucopyranosyl trichloroacetimidate
-
 Mycobacterium tuberculosis
6.3.1.13 5'-O-(N-(L-cysteinyl)-sulfamoyl) dequalinium chloride adenosine
-
 Mycobacterium tuberculosis
6.3.1.13 6-O-benzyl-2,3; 4,5-di-O-cyclohexylidene-(1R)-menthyloxycarbonyl-D-myo-inositol
-
 Mycobacterium tuberculosis
6.3.1.13 6-O-benzyl-2,3; 4,5-di-O-cyclohexylidene-D-myo-inositol
-
 Mycobacterium tuberculosis
6.3.1.13 6-O-benzyl-O-(3,4,6-tri-O-acetyl-2-deoxy-2-azido-alpha-D-glucopyranosyl)-(1 <->1)-2,3:4,5-di-O-cyclohexylidene-D-myo-inositol
-
 Mycobacterium tuberculosis
6.3.1.13 6-O-benzyl-O-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-alpha-D-glucopyranosyl)-(1<->1)-2,3:4,5-di-O-cyclohexylidene-D-myo-inositol
-
 Mycobacterium tuberculosis
6.3.1.13 dequalinium chloride
-
 Mycobacterium tuberculosis
6.3.1.13 additional information the enzyme structure is critical to developing potential inhibitors, synthesis of substrate analogues as potential inhibitors for the MshC enzyme. Target molecules are synthesized employing a Schmidt glycosylation strategy using an enantiomerically pure inositol acceptor and 2-deoxy trichloroacetimidate glycosyl donors with glycosylation yields greater than 70% and overall yields over 5%. The inositol acceptor is obtained via chiral resolution of myo-inositol Mycobacterium tuberculosis
6.3.1.13 NTF1836
-
 Mycobacterium tuberculosis
6.3.1.13 O-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-alpha-D-glucopyranosyl)-(1<->1)-2,3:4,5-di-O-cyclohexylidene-D-myo-inositol
-
 Mycobacterium tuberculosis

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
6.3.1.13 Mg2+ required Mycobacterium tuberculosis

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
6.3.1.13 1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + L-cysteine + ATP Mycobacterium tuberculosis
-
 1-O-[2-(L-cysteinamido)-2-deoxy-alpha-D-glucopyranosyl]-1D-myo-inositol + AMP + diphosphate
-
 ?
6.3.1.13 1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + L-cysteine + ATP Mycobacterium tuberculosis ATCC 25618 / H37Rv
-
 1-O-[2-(L-cysteinamido)-2-deoxy-alpha-D-glucopyranosyl]-1D-myo-inositol + AMP + diphosphate
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
6.3.1.13 Mycobacterium tuberculosis P9WJM9
-
-
6.3.1.13 Mycobacterium tuberculosis ATCC 25618 / H37Rv P9WJM9
-
-

Reaction

EC Number Reaction Comment Organism Reaction ID
6.3.1.13 1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + L-cysteine + ATP = 1-O-[2-(L-cysteinamido)-2-deoxy-alpha-D-glucopyranosyl]-1D-myo-inositol + AMP + diphosphate the mechanism of MshC has been proposed as bi-uni-uni-bi ping pong using steady state kinetics and positional isotope exchange studies. In the first phase of the enzymatic reaction, the nucleophilic attack of carboxylate of cysteine onto the phosphate of ATP leads to the formation of the cysteine-adenylate intermediate releasing inorganic diphosphate. This cysteine-adenylate intermediate is attacked by the amine of GlcN-Ins to form Cys-GlcN-Ins and in the process releases AMP, which completes the second phase of the enzymatic reaction, overview. During this stage, the reacting substrates and coenzymes are held in place by the amino acid residues W227, H55, T46, and D251 Mycobacterium tuberculosis
a

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
6.3.1.13 1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + L-cysteine + ATP
-
 Mycobacterium tuberculosis 1-O-[2-(L-cysteinamido)-2-deoxy-alpha-D-glucopyranosyl]-1D-myo-inositol + AMP + diphosphate
-
 ?
6.3.1.13 1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + L-cysteine + ATP
-
 Mycobacterium tuberculosis ATCC 25618 / H37Rv 1-O-[2-(L-cysteinamido)-2-deoxy-alpha-D-glucopyranosyl]-1D-myo-inositol + AMP + diphosphate
-
 ?

Synonyms

EC Number Synonyms Comment Organism
6.3.1.13 cysS2
-
 Mycobacterium tuberculosis
6.3.1.13 MshC
-
 Mycobacterium tuberculosis
6.3.1.13 MTCY261.29c
-
 Mycobacterium tuberculosis
6.3.1.13 mycothiol cysteine ligase
-
 Mycobacterium tuberculosis
6.3.1.13 Rv2130c
-
 Mycobacterium tuberculosis

Cofactor

EC Number Cofactor Comment Organism Structure
6.3.1.13 ATP
-
 Mycobacterium tuberculosis

General Information

EC Number General Information Comment Organism
6.3.1.13 metabolism mycothiol cysteine ligase (MshC) is a key enzyme in the mycothiol (MSH) biosynthesis, mycothiol biosynthesis and metabolic pathway, overview Mycobacterium tuberculosis
6.3.1.13 physiological function mycothiol cysteine ligase (MshC) is a key enzyme in the mycothiol (MSH) biosynthesis. The function of MshC is irreplaceable Mycobacterium tuberculosis