6.3.1.13: L-cysteine:1D-myo-inositol 2-amino-2-deoxy-alpha-D-glucopyranoside ligase
This is an abbreviated version!
For detailed information about L-cysteine:1D-myo-inositol 2-amino-2-deoxy-alpha-D-glucopyranoside ligase, go to the full flat file.
Word Map on EC 6.3.1.13
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6.3.1.13
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gsh
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oxygenase-1
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2-related
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nadph:quinone
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gamma-glutamate
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nrf2-are
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kelch-like
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nf-e2-related
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ech-associated
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oxidoreductase-1
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accys-glcn-ins
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erythroid-2-related
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drug development
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hemeoxygenase-1
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pharmacology
- 6.3.1.13
- gsh
- oxygenase-1
-
2-related
-
nadph:quinone
-
gamma-glutamate
-
nrf2-are
-
kelch-like
-
nf-e2-related
-
ech-associated
-
oxidoreductase-1
- accys-glcn-ins
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erythroid-2-related
- drug development
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hemeoxygenase-1
- pharmacology
Reaction
Synonyms
Cys:GlcN-Ins ligase, cysS2, cysteine ligase, L-cysteine:1-D-myo-inosityl 2-amino-2-deoxy-alpha-D-glucopyranoside ligase, More, MSH ligase, MshC, MshC ligase, MTCY261.29c, mycothiol cysteine ligase, mycothiol ligase, Rv2130c
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Substrates Products
Substrates Products on EC 6.3.1.13 - L-cysteine:1D-myo-inositol 2-amino-2-deoxy-alpha-D-glucopyranoside ligase
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REACTION DIAGRAM
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
additional information
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penultimate enzyme in the mycothiol biosynthetic pathway
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1-O-[2-(L-cysteinamido)-2-deoxy-alpha-D-glucopyranosyl]-1D-myo-inositol + AMP + diphosphate
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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
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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
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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
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enzyme is important in the biosynthesis of mycothiol, which plays a role in protecting bacteria against oxidative stress
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?
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
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the ATP-dependent ligation of Cys to GlcNIns is a key step in mycothiol biosynthesis, catalyzed by MshC, which is essential for growth of Mycobacterium tuberculosis
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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
Mycobacterium tuberculosis ATCC 25618 / H37Rv
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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
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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
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the ATP-dependent ligation of Cys to GlcNIns is a key step in mycothiol biosynthesis, catalyzed by MshC, which is essential for growth of Mycobacterium tuberculosis
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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
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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
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?
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
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?
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
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enzyme is important in the biosynthesis of mycothiol, which plays a role in protecting bacteria against oxidative stress
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?
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
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a key step in mycothiol, i.e. 1-D-myo-inosityl-2-(N-acetyl-L-cysteinyl)amido-2-deoxy-R-D-glucopyranoside or MSH or AcCys-GlcN-Ins, biosynthesis, mycothiol is produced to act against oxidative and antibiotic stress and is essential for cell growth, biosynthetic pathway, overview
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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
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key enzyme in the biosynthesis of mycothiol, pathway overview
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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
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the product 1D-myo-inositol 2-(L-cysteinyl)amido-2-deoxy-alpha-D-glucopyranoside is an intermediate in the biosynthetic pathway of mycothiol. Mycothiol is produced by Mycobacterium tuberculosis to maintain an intracellular reducing environment and protect against oxidative and antibiotic induced stress. The biosynthesis of mycothiol is essential for cell growth
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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
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positional isotope exchange analysis confirms that MshC catalyzes the formation of a kinetically competent cysteinyl-adenylate intermediate after the addition of ATP and cysteine
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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
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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
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enzyme is important in the biosynthesis of mycothiol, which plays a role in protecting bacteria against oxidative stress
-
?
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
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?
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
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inactivation of the mshC gene in RHA1 results in the accumulation of the MSH pathway intermediate, 1D-myo-inositol 2-amino-2-deoxy-alpha-D-glucopyranoside. The mutant is deficient in the biochemical degradation of a number of xenobiotics metabolized by the parent strain, it shows increased susceptibility to a number of antibiotics and it shows unusual growth characteristics, exhibiting a long lag phase before normal exponential growth
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