Any feedback?
Enzyme Nomenclature
Information on EC 2.4.1.250 - D-inositol-3-phosphate glycosyltransferase
for references in articles please use BRENDA:EC2.4.1.250Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
EC Tree
2.4.1.250 D-inositol-3-phosphate glycosyltransferaseIUBMB Comments
The enzyme, which belongs to the GT-B fold superfamily, catalyses the first dedicated reaction in the biosynthesis of mycothiol . The substrate was initially believed to be inositol, but eventually shown to be D-myo-inositol 3-phosphate . A substantial conformational change occurs upon UDP binding, which generates the binding site for D-myo-inositol 3-phosphate .
Specify your search results
The expected taxonomic range for this enzyme is: Bacteria, Archaea, Eukaryota
Reaction Schemes
topPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
MshA
MSMEG0924
mycothiol glycosyltransferases
-
-
-
-
MshA
-
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
UDP-N-acetyl-alpha-D-glucosamine + 1D-myo-inositol 3-phosphate = 1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol 3-phosphate + UDP
UDP-N-acetyl-alpha-D-glucosamine + 1D-myo-inositol 3-phosphate = 1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol 3-phosphate + UDP
-
-
-
-
UDP-N-acetyl-alpha-D-glucosamine + 1D-myo-inositol 3-phosphate = 1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol 3-phosphate + UDP
1D-myo-inositol 3-phosphate i.e. 1L-myo-inositol 1-phosphate
-
UDP-N-acetyl-alpha-D-glucosamine + 1D-myo-inositol 3-phosphate = 1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol 3-phosphate + UDP
1D-myo-inositol 3-phosphate i.e. 1L-myo-inositol 1-phosphate
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PATHWAY SOURCE
PATHWAYS
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SYSTEMATIC NAME
IUBMB Comments
UDP-N-acetyl-D-glucosamine:1D-myo-inositol 3-phosphate alpha-D-glycosyltransferase
The enzyme, which belongs to the GT-B fold superfamily, catalyses the first dedicated reaction in the biosynthesis of mycothiol [1]. The substrate was initially believed to be inositol, but eventually shown to be D-myo-inositol 3-phosphate [2]. A substantial conformational change occurs upon UDP binding, which generates the binding site for D-myo-inositol 3-phosphate [3].
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
1D-myo-inositol 3-phosphate + UDP-N-acetyl-alpha-D-glucosamine
1D-myo-inositol 2-acetamido-2-deoxy-alpha-D-glucopyranoside 3-phosphate + UDP
UDP-N-acetyl-D-glucosamine + 1D-myo-inositol 3-phosphate
1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol 3-phosphate + UDP
1D-myo-inositol 3-phosphate + UDP-N-acetyl-alpha-D-glucosamine
1D-myo-inositol 2-acetamido-2-deoxy-alpha-D-glucopyranoside 3-phosphate + UDP
the reaction proceeds via a front-side SNi-like concerted reaction mechanism
-
-
?
1D-myo-inositol 3-phosphate + UDP-N-acetyl-alpha-D-glucosamine
1D-myo-inositol 2-acetamido-2-deoxy-alpha-D-glucopyranoside 3-phosphate + UDP
the reaction proceeds via a front-side SNi-like concerted reaction mechanism
-
-
?
UDP-N-acetyl-D-glucosamine + 1D-myo-inositol 1-phosphate
?
at 10% of the activity with 1D-myo-inositol 3-phosphate
-
-
?
UDP-N-acetyl-D-glucosamine + 1D-myo-inositol 1-phosphate
?
Mycolicibacterium smegmatis mc(2)155 / ATCC 700084
at 10% of the activity with 1D-myo-inositol 3-phosphate
-
-
?
UDP-N-acetyl-D-glucosamine + 1D-myo-inositol 3-phosphate
1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol 3-phosphate + UDP
-
1D-myo-inositol 3-phosphate i.e. 1L-myo-inositol 1-phosphate, committed step of mycothiol biosynthesis
-
-
?
UDP-N-acetyl-D-glucosamine + 1D-myo-inositol 3-phosphate
1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol 3-phosphate + UDP
-
1D-myo-inositol 3-phosphate i.e. 1L-myo-inositol 1-phosphate. Molecular models of the ternary complex suggest a mechanism in which the beta-phosphate of the substrate, UDP-N-acetylglucosamine, promotes the nucleophilic attack of the 3-hydroxyl group of 1D-myo-inositol 3-phosphate while at the same time promoting the cleavage of the sugar nucleotide bond
-
-
?
UDP-N-acetyl-D-glucosamine + 1D-myo-inositol 3-phosphate
1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol 3-phosphate + UDP
-
1D-myo-inositol 3-phosphate i.e. 1L-myo-inositol 1-phosphate, the mshA gene is essential for the growth of Mycobacterium tuberculosis
-
-
?
UDP-N-acetyl-D-glucosamine + 1D-myo-inositol 3-phosphate
1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol 3-phosphate + UDP
-
1D-myo-inositol 3-phosphate i.e. 1L-myo-inositol 1-phosphate
-
-
?
UDP-N-acetyl-D-glucosamine + 1D-myo-inositol 3-phosphate
1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol 3-phosphate + UDP
-
1D-myo-inositol 3-phosphate i.e. 1L-myo-inositol 1-phosphate, the mshA gene is essential for the growth of Mycobacterium tuberculosis
-
-
?
UDP-N-acetyl-D-glucosamine + 1D-myo-inositol 3-phosphate
1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol 3-phosphate + UDP
-
1D-myo-inositol 3-phosphate i.e. 1L-myo-inositol 1-phosphate
-
-
?
UDP-N-acetyl-D-glucosamine + 1D-myo-inositol 3-phosphate
1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol 3-phosphate + UDP
-
1D-myo-inositol 3-phosphate i.e. 1L-myo-inositol 1-phosphate, mycothiol biosynthesis
-
-
?
UDP-N-acetyl-D-glucosamine + 1D-myo-inositol 3-phosphate
1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol 3-phosphate + UDP
1D-myo-inositol 3-phosphate i.e. 1L-myo-inositol 1-phosphate, mycothiol biosynthesis
-
-
?
UDP-N-acetyl-D-glucosamine + 1D-myo-inositol 3-phosphate
1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol 3-phosphate + UDP
1D-myo-inositol 3-phosphate i.e. 1L-myo-inositol 1-phosphate. Little activity is obtained with myo-inositol, 1D-myo-inositol 1-phosphate, or myo-inositol 2-phosphate as the N-acetylglucosamine acceptor. 1D-myo-inositol 1-phosphate is neither a good substrate nor an inhibitor of MshA. Therfore the commercially available 1DL-myo-inositol 1-phosphate can be used as substrate for MshA assays without complications
-
-
?
UDP-N-acetyl-D-glucosamine + 1D-myo-inositol 3-phosphate
1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol 3-phosphate + UDP
Mycolicibacterium smegmatis mc(2)155 / ATCC 700084
1D-myo-inositol 3-phosphate i.e. 1L-myo-inositol 1-phosphate, mycothiol biosynthesis
-
-
?
UDP-N-acetyl-D-glucosamine + 1D-myo-inositol 3-phosphate
1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol 3-phosphate + UDP
Mycolicibacterium smegmatis mc(2)155 / ATCC 700084
1D-myo-inositol 3-phosphate i.e. 1L-myo-inositol 1-phosphate. Little activity is obtained with myo-inositol, 1D-myo-inositol 1-phosphate, or myo-inositol 2-phosphate as the N-acetylglucosamine acceptor. 1D-myo-inositol 1-phosphate is neither a good substrate nor an inhibitor of MshA. Therfore the commercially available 1DL-myo-inositol 1-phosphate can be used as substrate for MshA assays without complications
-
-
?
UDP-N-acetyl-D-glucosamine + myo-inositol 2-phosphate
?
at 10% of the activity with 1D-myo-inositol 3-phosphate
-
-
?
UDP-N-acetyl-D-glucosamine + myo-inositol 2-phosphate
?
Mycolicibacterium smegmatis mc(2)155 / ATCC 700084
at 10% of the activity with 1D-myo-inositol 3-phosphate
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
UDP-N-acetyl-D-glucosamine + 1D-myo-inositol 3-phosphate
1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol 3-phosphate + UDP
UDP-N-acetyl-D-glucosamine + 1D-myo-inositol 3-phosphate
1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol 3-phosphate + UDP
-
1D-myo-inositol 3-phosphate i.e. 1L-myo-inositol 1-phosphate, committed step of mycothiol biosynthesis
-
-
?
UDP-N-acetyl-D-glucosamine + 1D-myo-inositol 3-phosphate
1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol 3-phosphate + UDP
-
1D-myo-inositol 3-phosphate i.e. 1L-myo-inositol 1-phosphate, the mshA gene is essential for the growth of Mycobacterium tuberculosis
-
-
?
UDP-N-acetyl-D-glucosamine + 1D-myo-inositol 3-phosphate
1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol 3-phosphate + UDP
-
1D-myo-inositol 3-phosphate i.e. 1L-myo-inositol 1-phosphate, the mshA gene is essential for the growth of Mycobacterium tuberculosis
-
-
?
UDP-N-acetyl-D-glucosamine + 1D-myo-inositol 3-phosphate
1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol 3-phosphate + UDP
-
1D-myo-inositol 3-phosphate i.e. 1L-myo-inositol 1-phosphate, mycothiol biosynthesis
-
-
?
UDP-N-acetyl-D-glucosamine + 1D-myo-inositol 3-phosphate
1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol 3-phosphate + UDP
1D-myo-inositol 3-phosphate i.e. 1L-myo-inositol 1-phosphate, mycothiol biosynthesis
-
-
?
UDP-N-acetyl-D-glucosamine + 1D-myo-inositol 3-phosphate
1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol 3-phosphate + UDP
Mycolicibacterium smegmatis mc(2)155 / ATCC 700084
1D-myo-inositol 3-phosphate i.e. 1L-myo-inositol 1-phosphate, mycothiol biosynthesis
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
1D-myo-inositol 1-phosphate is neither a good substrate nor an inhibitor of MshA. Therefore the commercially available 1DL-myo-inositol 1-phosphate can be used as substrate for MshA assays without complications
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
metabolism
physiological function
malfunction
-
characterization of mutant mshA::Tn5 which is defective in MshA produces no measurable amount of the pseudodisaccharide precursors of mycothiol, 1D-myo-inosityl 2-acetamido-2-deoxy-alpha-D-glucopyranoside and 1D-myo-inosityl 2-amino-2-deoxy-alpha-D-glucopyranoside
malfunction
-
inability to disrupt the mshA gene in Mycobacterium tuberculosis containing a single copy of mshA. Directed knock-out of the mshA gene in Mycobacterium tuberculosis Erdman is only possible when a second copy of mshA is first incorporated into the chromosome. Bacteria with only a single copy of mshA that grew after mutagenesis produced normal levels of mycothiol
malfunction
-
seven independent missense or frameshift mutations within mshA are identified and characterized. Precise null deletion mutations of the mshA gene are generated by specialized transduction in three different strains of Mycobacterium tuberculosis. The mshA deletion mutants are defective in mycothiol biosynthesis, are only ethionamide-resistant and require catalase to grow. Biochemical studies suggest that the mechanism of ethionamide resistance in mshA mutants is likely due to a defect in ethionamide activation. In vivo, a mycothiol-deficient strain grows normally in immunodeficient mice, but is slightly defective for growth in immunocompetent mice. Mutations in mshA demonstrate the nonessentiality of mycothiol for growth in vitro and in vivo
malfunction
-
inability to disrupt the mshA gene in Mycobacterium tuberculosis containing a single copy of mshA. Directed knock-out of the mshA gene in Mycobacterium tuberculosis Erdman is only possible when a second copy of mshA is first incorporated into the chromosome. Bacteria with only a single copy of mshA that grew after mutagenesis produced normal levels of mycothiol
-
metabolism
key enzyme responsible for the first step of mycothiol biosynthesis
metabolism
-
key enzyme responsible for the first step of mycothiol biosynthesis
-
physiological function
overexpression of the gene, MshA, coding for mycothiol glycosyl transferase improves the robustness of Corynebacterium glutamicum to various stresses. Intracellular mycothiol content is increased by 114% upon overexpression of MshA. Survival rates increased by 44, 39, 90, 77, 131, 87, 52, 47, 57, 85 and 33% as compared to wild-type under stress by H2O2 (40 mM), methylglyoxal (5.8 mM), erythromycin (0.08 mg/ml), streptomycin (0.005 mg/ml), Cd2+ (0.01 mM), Mn2+ (2 mM), formic acid (0.05%), acetic acid (0.15%), levulinic acid (0.25%), furfural (7.2 mM), and ethanol (10% v/v), respectively. Increased mycothiol content also decreases the concentration of reactive oxygen species in the presence of the above stresses
physiological function
-
overexpression of the gene, MshA, coding for mycothiol glycosyl transferase improves the robustness of Corynebacterium glutamicum to various stresses. Intracellular mycothiol content is increased by 114% upon overexpression of MshA. Survival rates increased by 44, 39, 90, 77, 131, 87, 52, 47, 57, 85 and 33% as compared to wild-type under stress by H2O2 (40 mM), methylglyoxal (5.8 mM), erythromycin (0.08 mg/ml), streptomycin (0.005 mg/ml), Cd2+ (0.01 mM), Mn2+ (2 mM), formic acid (0.05%), acetic acid (0.15%), levulinic acid (0.25%), furfural (7.2 mM), and ethanol (10% v/v), respectively. Increased mycothiol content also decreases the concentration of reactive oxygen species in the presence of the above stresses
-
Show AA Sequence and Transmembrane Helices (7285 entries)
Longer loading times are possible. Please use the AA Sequence and Transmembrane Helices Search for a specific query.
Longer loading times are possible. Please use the AA Sequence and Transmembrane Helices Search for a specific query.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
vapor diffusion under silicon oil. The structure of MshA is determined both in the absence of substrates and in a complex with UDP and 11D-myo-inositol 3-phosphate. The structure of unliganded CgMshA (APO form) is determined by single isomorphous replacement with anomalous scattering utilizing a CuKalpha home source and a mercury derivative to 2.1 A resolution. Crystallization of CgMshA in the presence of UDP or UDP-GlcNAc results in a tetragonal crystal form. The structure of MshA from Corynebacterium glutamicum is determined both in the absence of substrates and in a complex with UDP and 1L-myo-inositol-1-phosphate
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
construction of Mycobacterium tuberculosis with two copies of mshA
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Buchmeier, N.; Fahey, R.C.
The mshA gene encoding the glycosyltransferase of mycothiol biosynthesis is essential in Mycobacterium tuberculosis Erdman
FEMS Microbiol. Lett.
264
74-79
2006
Mycobacterium tuberculosis, Mycobacterium tuberculosis Erdman
brenda
Newton, G.L.; Koledin, T.; Gorovitz, B.; Rawat, M.; Fahey, R.C.; Av-Gay, Y.
The glycosyltransferase gene encoding the enzyme catalyzing the first step of mycothiol biosynthesis (mshA)
J. Bacteriol.
185
3476-3479
2003
Mycolicibacterium smegmatis
brenda
Newton, G.L.; Ta, P.; Bzymek, K.P.; Fahey, R.C.
Biochemistry of the initial steps of mycothiol biosynthesis
J. Biol. Chem.
281
33910-33920
2006
Mycolicibacterium smegmatis (A0QQY9), Mycolicibacterium smegmatis mc(2)155 / ATCC 700084 (A0QQY9)
brenda
Vetting, M.W.; Frantom, P.A.; Blanchard, J.S.
Structural and enzymatic analysis of MshA from Corynebacterium glutamicum: substrate-assisted catalysis
J. Biol. Chem.
283
15834-15844
2008
Corynebacterium glutamicum
brenda
Vilcheze, C.; Av-Gay, Y.; Attarian, R.; Liu, Z.; Hazbon, M.H.; Colangeli, R.; Chen, B.; Liu, W.; Alland, D.; Sacchettini, J.C.; Jacobs, W.R. Jr.
Mycothiol biosynthesis is essential for ethionamide susceptibility in Mycobacterium tuberculosis
Mol. Microbiol.
69
1316-1329
2008
Mycobacterium tuberculosis
brenda
Liu, Y.B.; Chen, C.; Chaudhry, M.T.; Si, M.R.; Zhang, L.; Wang, Y.; Shen, X.H.
Enhancing Corynebacterium glutamicum robustness by over-expressing a gene, mshA, for mycothiol glycosyltransferase
Biotechnol. Lett.
36
1453-1459
2014
Corynebacterium glutamicum (Q8NTA6), Corynebacterium glutamicum DSM 20300 (Q8NTA6)
brenda
Blanco Capurro, J.I.; Hopkins, C.W.; Pierdominici Sottile, G.; Gonzalez Lebrero, M.C.; Roitberg, A.E.; Marti, M.A.
Theoretical insights into the reaction and inhibition mechanism of metal-independent retaining glycosyltransferase responsible for mycothiol biosynthesis
J. Phys. Chem. B
121
471-478
2017
Corynebacterium glutamicum (Q8NTA6), Corynebacterium glutamicum ATCC 13032 (Q8NTA6)
brenda
Select items on the left to see more content.
EXTERNAL LINKS (specific for EC-Number 2.4.1.250)
html completed
Use of this online version of BRENDA is free under the CC BY 4.0 license. See terms of use for full details.
Release 2023.1 (January 2023)
About BRENDA
Social media
Help
Survey
Download
Contribution
Legal
Curated at
Member of
