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Ligand 1D-myo-inositol 2-amino-2-deoxy-alpha-D-glucopyranoside

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (1 result)

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Show Natural Substrate (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

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

744634, 745132, 650166, 672220, 676970, 671300, 695095, 690956

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In Vivo Product in Enzyme-catalyzed Reactions (5 results)

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Show Natural Product (5 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.5.1.103

1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O = 1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate

0

-

3.5.1.103

1-D-myo-inosityl-2-acetamido-2-deoxy-alpha-D-glucopyranoside + H2O = 1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate

0

-

3.5.1.103

N-acetyl-1-D-myo-inosityl-2-amino-2-deoxy-alpha-D-glucopyranoside + H2O = 1-D-myo-inosityl-2-amino-2-deoxy-alpha-D-glucopyranoside + acetate

0

-

3.5.1.103

1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-D-myo-inositol + H2O = 1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-D-myo-inositol + acetate

0

-

3.5.1.103

4 entries

3.5.1.115

a mycothiol S-conjugate + H2O = an N-acetyl L-cysteine-S-conjugate + 1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol

0

-

Substrate in Enzyme-catalyzed Reactions (1 result)

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Show Substrate (1 entry)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

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

650166, 672220, 676970, 671300, 744634, 745132, 695095, 690956

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Product in Enzyme-catalyzed Reactions (9 results)

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Show Product (9 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.5.1.103

1-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + H2O = 1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate

0

-

3.5.1.103

1-D-myo-inosityl-2-acetamido-2-deoxy-alpha-D-glucopyranoside + H2O = 1-(2-amino-2-deoxy-alpha-D-glucopyranoside)-1D-myo-inositol + acetate

0

-

3.5.1.103

N-acetyl-1-D-myo-inosityl-2-amino-2-deoxy-alpha-D-glucopyranoside + H2O = 1-D-myo-inosityl-2-amino-2-deoxy-alpha-D-glucopyranoside + acetate

0

-

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

0

-

3.5.1.103

N-acetyl-1-D-myo-inosityl-2-amino-2-deoxy-D-glucopyranoside + H2O = 1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol + acetate

0

-

3.5.1.103

1-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-D-myo-inositol + H2O = 1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-D-myo-inositol + acetate

0

-

3.5.1.115

RifS13 + H2O = 1-D-myo-inositol-alpha-D-glucopyranoside + N-acetyl-S-[(2R,12Z,14E,16S,18S,19S,20S,21S,22S,23S,24E)-5,6,9,17,19-pentahydroxy-23-methoxy-21-(methoxycarbonyl)-2,4,12,16,18,20,22-heptamethyl-1,11-dioxo-1,2-dihydro-2,7-(epoxypentadeca[1,11,13]trienoimino)naphtho[2,1-b]furan-8-yl]-L-cysteine

0

-

3.5.1.115

RifS17 + H2O = 1-D-myo-inositol-alpha-D-glucopyranoside + N-acetyl-S-[(2R,12Z,14E,16S,18S,19S,20S,21S,22S,23S,24E)-5,17,19-trihydroxy-23-methoxy-21-(methoxycarbonyl)-2,4,12,16,18,20,22-heptamethyl-1,6,9,11-tetraoxo-1,2,6,9-tetrahydro-2,7-(epoxypentadeca[1,11,13]trienoimino)naphtho[2,1-b]furan-8-yl]-L-cysteine

0

-

3.5.1.115

a mycothiol S-conjugate + H2O = an N-acetyl L-cysteine-S-conjugate + 1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-1D-myo-inositol

0

-

3.5.1.103

6 entries

3.5.1.115

3 entries

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (1 result)

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Show Turnover Number (1 entry)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

6.3.1.13

3.15

-

pH 7.8, 25°C, recombinant enzyme

672220

K_M Value (2 results)

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Show KM Value (2 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

6.3.1.13

0.072

-

pH 7.5, 37°C

650166

6.3.1.13

0.16

-

pH 7.8, 25°C, recombinant enzyme

672220

6.3.1.13

2 entries

References & Links

Literature References (8)

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Show Reference (8 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

650166

12033919

ATP-dependent L-cysteine:1D-myo-inosityl 2-amino-2-deoxy-alpha-D-glucopyranoside ligase, mycothiol biosynthesis enzyme MshC, is related to class I cysteinyl-tRNA synthetases

2002

Sareen, D.; Steffek, M.; Newton, G.L.; Fahey, R.C.

Biochemistry

41

6885-6890

671300

16674910

A coupled spectrophotometric assay for l-cysteine:1-D-myo-inosityl 2-amino-2-deoxy-alpha-D-glucopyranoside ligase and its application for inhibitor screening

2006

Newton, G.L.; Ta, P.; Sareen, D.; Fahey, R.C.

Anal. Biochem.

353

167-173

672220

17848100

Steady-state and pre-steady-state kinetic analysis of Mycobacterium smegmatis cysteine ligase (MshC)

2007

Fan, F.; Luxenburger, A.; Painter, G.F.; Blanchard, J.S.

Biochemistry

46

11421-11429

676970

16908186

Cloning, expression and rapid purification of active recombinant mycothiol ligase as B1 immunoglobulin binding domain of streptococcal protein G, glutathione-S-transferase and maltose binding protein fusion proteins in Mycobacterium smegmatis

2006

Gutierrez-Lugo, M.T.; Newton, G.L.; Fahey, R.C.; Bewley, C.A.

Protein Expr. Purif.

50

128-136

690956

18373355

Positional isotope exchange analysis of the Mycobacterium smegmatis cysteine ligase (MshC)

2008

Williams, L.; Fan, F.; Blanchard, J.S.; Raushel, F.M.

Biochemistry

47

4843-4850

695095

18832026

Characterization of a mycothiol ligase mutant of Rhodococcus jostii RHA1

2008

Dosanjh, M.; Newton, G.L.; Davies, J.

Res. Microbiol.

159

643-650

744634

29107814

Synthesis of substrate analogues as potential inhibitors for Mycobacterium tuberculosis enzyme MshC

2017

Patel, K.; Song, F.; Andreana, P.R.

Carbohydr. Res.

453-454

10-18

745132

27321674

S-nitrosomycothiol reductase and mycothiol are required for survival under aldehyde stress and biofilm formation in Mycobacterium smegmatis

2016

Vargas, D.; Hageman, S.; Gulati, M.; Nobile, C.J.; Rawat, M.

IUBMB Life

68

621-628

Links to other databases for 1D-myo-inositol 2-amino-2-deoxy-alpha-D-glucopyranoside

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Show Links (1 entry)

ChEBI

PubChem