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Ligand (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

BRENDA

benzoxazinoid glucosides biosynthesis, tryptophan metabolism

KEGG

Benzoxazinoid biosynthesis, Biosynthesis of alkaloids derived from shikimate pathway, Biosynthesis of amino acids, Biosynthesis of secondary metabolites, Biosynthesis of various plant secondary metabolites, Indole diterpene alkaloid biosynthesis, Phenylalanine, tyrosine and tryptophan biosynthesis more

MetaCyc

DIBOA-glucoside biosynthesis, L-tryptophan biosynthesis, paspaline biosynthesis

Show all BRENDA pathways known for (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (18 results)

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Show Natural Substrate (18 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.1.2.8

(1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate = indole + D-glyceraldehyde 3-phosphate

691784, 691511, 693498

-

4.1.2.8

indole-3-glycerol phosphate = indole + glyceraldehyde 3-phosphate

670884, 670717, 670511, 666055

-

4.2.1.20

(1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate + L-serine = L-tryptophan + D-glyceraldehyde 3-phosphate + H2O

692750, 694748

1a5b, 3D-view

4.2.1.20

(1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate + L-serine = L-tryptophan + D-glyceraldehyde 3-phosphate + H2O

692750, 694748

1qoq, 3D-view

4.2.1.20

(1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate + L-serine = L-tryptophan + D-glyceraldehyde 3-phosphate + H2O

692750, 694748

2rh9, 3D-view

4.2.1.20

(1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate + L-serine = L-tryptophan + D-glyceraldehyde 3-phosphate + H2O

692750, 694748

2rhg, 3D-view

4.2.1.20

L-serine + 1-C-(indol-3-yl)glycerol 3-phosphate = L-tryptophan + D-glyceraldehyde 3-phosphate + H2O

728850, 729226, 729240, 729952, 730212, 730868, 747735, 730007, 727489, 729099

1a5b, 3D-view

4.2.1.20

L-serine + 1-C-(indol-3-yl)glycerol 3-phosphate = L-tryptophan + D-glyceraldehyde 3-phosphate + H2O

728850, 729226, 729240, 729952, 730212, 730868, 747735, 730007, 727489, 729099

1qoq, 3D-view

4.2.1.20

L-serine + 1-C-(indol-3-yl)glycerol 3-phosphate = L-tryptophan + D-glyceraldehyde 3-phosphate + H2O

728850, 729226, 729240, 729952, 730212, 730868, 747735, 730007, 727489, 729099

2rh9, 3D-view

4.2.1.20

L-serine + 1-C-(indol-3-yl)glycerol 3-phosphate = L-tryptophan + D-glyceraldehyde 3-phosphate + H2O

728850, 729226, 729240, 729952, 730212, 730868, 747735, 730007, 727489, 729099

2rhg, 3D-view

4.2.1.20

L-serine + 1-C-(indol-3-yl)glycerol 3-phosphate = L-tryptophan + glyceraldehyde 3-phosphate + H2O

715294, 714182, 694034

1a5b, 3D-view

4.2.1.20

L-serine + 1-C-(indol-3-yl)glycerol 3-phosphate = L-tryptophan + glyceraldehyde 3-phosphate + H2O

715294, 714182, 694034

1qoq, 3D-view

4.2.1.20

L-serine + 1-C-(indol-3-yl)glycerol 3-phosphate = L-tryptophan + glyceraldehyde 3-phosphate + H2O

715294, 714182, 694034

2rh9, 3D-view

4.2.1.20

L-serine + 1-C-(indol-3-yl)glycerol 3-phosphate = L-tryptophan + glyceraldehyde 3-phosphate + H2O

715294, 714182, 694034

2rhg, 3D-view

4.2.1.20

indoleglycerol phosphate = indole + D-glyceraldehyde 3-phosphate

727489

1a5b, 3D-view

4.2.1.20

indoleglycerol phosphate = indole + D-glyceraldehyde 3-phosphate

727489

1qoq, 3D-view

4.2.1.20

indoleglycerol phosphate = indole + D-glyceraldehyde 3-phosphate

727489

2rh9, 3D-view

4.2.1.20

indoleglycerol phosphate = indole + D-glyceraldehyde 3-phosphate

727489

2rhg, 3D-view

4.1.2.8

2 entries

4.2.1.20

16 entries

In Vivo Product in Enzyme-catalyzed Reactions (6 results)

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Show Natural Product (6 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.1.1.48

1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate = 1-(3-indolyl)glycerol-3-phosphate + CO2 + H2O

0

1a53, 3D-view

4.1.1.48

1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate = 1-(3-indolyl)glycerol-3-phosphate + CO2 + H2O

0

3t44, 3D-view

4.1.1.48

1-(2-Carboxyphenylamino)-1-deoxy-D-ribulose-5-phosphate = 1-(3-Indolyl)glycerol-3-phosphate + CO2 + H2O

652796

1a53, 3D-view

4.1.1.48

1-(2-Carboxyphenylamino)-1-deoxy-D-ribulose-5-phosphate = 1-(3-Indolyl)glycerol-3-phosphate + CO2 + H2O

652796

3t44, 3D-view

4.1.1.48

1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate = 1-C-(indol-3-yl)glycerol 3-phosphate + CO2 + H2O

0

1a53, 3D-view

4.1.1.48

1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate = 1-C-(indol-3-yl)glycerol 3-phosphate + CO2 + H2O

0

3t44, 3D-view

4.1.1.48

6 entries

Substrate in Enzyme-catalyzed Reactions (31 results)

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Show Substrate (31 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.1.2.8

(1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate = indole + D-glyceraldehyde 3-phosphate

691784, 691511, 693498, 728444

-

4.1.2.8

indole-3-glycerol phosphate = indole + D-glyceraldehyde 3-phosphate

695226, 691963

-

4.1.2.8

indole-3-glycerol phosphate = indole + glyceraldehyde 3-phosphate

670511, 670884, 670717, 666055

-

4.2.1.20

(1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate + L-serine = L-tryptophan + D-glyceraldehyde 3-phosphate + H2O

692750, 694748

1a5b, 3D-view

4.2.1.20

(1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate + L-serine = L-tryptophan + D-glyceraldehyde 3-phosphate + H2O

692750, 694748

1qoq, 3D-view

4.2.1.20

(1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate + L-serine = L-tryptophan + D-glyceraldehyde 3-phosphate + H2O

692750, 694748

2rh9, 3D-view

4.2.1.20

(1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate + L-serine = L-tryptophan + D-glyceraldehyde 3-phosphate + H2O

692750, 694748

2rhg, 3D-view

4.2.1.20

1-C-(indol-3-yl)glycerol 3-phosphate = D-glyceraldehyde 3-phosphate + indole

729952

1a5b, 3D-view

4.2.1.20

1-C-(indol-3-yl)glycerol 3-phosphate = D-glyceraldehyde 3-phosphate + indole

729952

1qoq, 3D-view

4.2.1.20

1-C-(indol-3-yl)glycerol 3-phosphate = D-glyceraldehyde 3-phosphate + indole

729952

2rh9, 3D-view

4.2.1.20

1-C-(indol-3-yl)glycerol 3-phosphate = D-glyceraldehyde 3-phosphate + indole

729952

2rhg, 3D-view

4.2.1.20

L-serine + 1-C-(indol-3-yl)glycerol 3-phosphate = L-tryptophan + D-glyceraldehyde 3-phosphate + H2O

728850, 729226, 729240, 729952, 747116, 730212, 730868, 747735, 730007, 727489, 729099

1a5b, 3D-view

4.2.1.20

L-serine + 1-C-(indol-3-yl)glycerol 3-phosphate = L-tryptophan + D-glyceraldehyde 3-phosphate + H2O

728850, 729226, 729240, 729952, 747116, 730212, 730868, 747735, 730007, 727489, 729099

1qoq, 3D-view

4.2.1.20

L-serine + 1-C-(indol-3-yl)glycerol 3-phosphate = L-tryptophan + D-glyceraldehyde 3-phosphate + H2O

728850, 729226, 729240, 729952, 747116, 730212, 730868, 747735, 730007, 727489, 729099

2rh9, 3D-view

4.2.1.20

L-serine + 1-C-(indol-3-yl)glycerol 3-phosphate = L-tryptophan + D-glyceraldehyde 3-phosphate + H2O

728850, 729226, 729240, 729952, 747116, 730212, 730868, 747735, 730007, 727489, 729099

2rhg, 3D-view

4.2.1.20

L-serine + 1-C-(indol-3-yl)glycerol 3-phosphate = L-tryptophan + glyceraldehyde 3-phosphate + H2O

694034, 715294, 714182

1a5b, 3D-view

4.2.1.20

L-serine + 1-C-(indol-3-yl)glycerol 3-phosphate = L-tryptophan + glyceraldehyde 3-phosphate + H2O

694034, 715294, 714182

1qoq, 3D-view

4.2.1.20

L-serine + 1-C-(indol-3-yl)glycerol 3-phosphate = L-tryptophan + glyceraldehyde 3-phosphate + H2O

694034, 715294, 714182

2rh9, 3D-view

4.2.1.20

L-serine + 1-C-(indol-3-yl)glycerol 3-phosphate = L-tryptophan + glyceraldehyde 3-phosphate + H2O

694034, 715294, 714182

2rhg, 3D-view

4.2.1.20

L-threonine + 1-C-(indol-3-yl)glycerol 3-phosphate = (2S,3S)-beta-methyltryptophan + D-glyceraldehyde 3-phosphate + H2O

747116

1a5b, 3D-view

4.2.1.20

L-threonine + 1-C-(indol-3-yl)glycerol 3-phosphate = (2S,3S)-beta-methyltryptophan + D-glyceraldehyde 3-phosphate + H2O

747116

1qoq, 3D-view

4.2.1.20

L-threonine + 1-C-(indol-3-yl)glycerol 3-phosphate = (2S,3S)-beta-methyltryptophan + D-glyceraldehyde 3-phosphate + H2O

747116

2rh9, 3D-view

4.2.1.20

L-threonine + 1-C-(indol-3-yl)glycerol 3-phosphate = (2S,3S)-beta-methyltryptophan + D-glyceraldehyde 3-phosphate + H2O

747116

2rhg, 3D-view

4.2.1.20

indole-3-glycerol phosphate = indole + D-glyceraldehyde 3-phosphate

5568, 5569, 5559, 5570, 5560, 5548, 5567, 5555, 5566, 5557, 5550, 5563, 666055, 730007

1a5b, 3D-view

4.2.1.20

indole-3-glycerol phosphate = indole + D-glyceraldehyde 3-phosphate

5568, 5569, 5559, 5570, 5560, 5548, 5567, 5555, 5566, 5557, 5550, 5563, 666055, 730007

1qoq, 3D-view

4.2.1.20

indole-3-glycerol phosphate = indole + D-glyceraldehyde 3-phosphate

5568, 5569, 5559, 5570, 5560, 5548, 5567, 5555, 5566, 5557, 5550, 5563, 666055, 730007

2rh9, 3D-view

4.2.1.20

indole-3-glycerol phosphate = indole + D-glyceraldehyde 3-phosphate

5568, 5569, 5559, 5570, 5560, 5548, 5567, 5555, 5566, 5557, 5550, 5563, 666055, 730007

2rhg, 3D-view

4.2.1.20

indoleglycerol phosphate = indole + D-glyceraldehyde 3-phosphate

727489

1a5b, 3D-view

4.2.1.20

indoleglycerol phosphate = indole + D-glyceraldehyde 3-phosphate

727489

1qoq, 3D-view

4.2.1.20

indoleglycerol phosphate = indole + D-glyceraldehyde 3-phosphate

727489

2rh9, 3D-view

4.2.1.20

indoleglycerol phosphate = indole + D-glyceraldehyde 3-phosphate

727489

2rhg, 3D-view

4.1.2.8

3 entries

4.2.1.20

28 entries

Product in Enzyme-catalyzed Reactions (19 results)

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Show Product (19 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.2.14

phosphoribosylanthranilate = indoleglycerol phosphate + CO2 + H2O

0

-

4.1.1.48

1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate = 1-(3-indolyl)glycerol-3-phosphate + CO2 + H2O

0

1a53, 3D-view

4.1.1.48

1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate = 1-(3-indolyl)glycerol-3-phosphate + CO2 + H2O

0

3t44, 3D-view

4.1.1.48

1-(2-Carboxyphenylamino)-1-deoxy-D-ribulose-5-phosphate = 1-(3-Indolyl)glycerol-3-phosphate + CO2 + H2O

4596, 4606, 4600, 4593, 4598, 4602, 4609, 4611, 4612, 4614, 4615, 4594, 4597, 4603, 4604, 4599, 4616, 4608, 4605, 4607, 4601, 4595, 0, 4610, 4613, 4592, 648890, 652796

1a53, 3D-view

4.1.1.48

1-(2-Carboxyphenylamino)-1-deoxy-D-ribulose-5-phosphate = 1-(3-Indolyl)glycerol-3-phosphate + CO2 + H2O

4596, 4606, 4600, 4593, 4598, 4602, 4609, 4611, 4612, 4614, 4615, 4594, 4597, 4603, 4604, 4599, 4616, 4608, 4605, 4607, 4601, 4595, 0, 4610, 4613, 4592, 648890, 652796

3t44, 3D-view

4.1.1.48

1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate = 1-C-(indol-3-yl)glycerol 3-phosphate + CO2 + H2O

0

1a53, 3D-view

4.1.1.48

1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate = 1-C-(indol-3-yl)glycerol 3-phosphate + CO2 + H2O

0

3t44, 3D-view

4.1.1.48

1-(2-carboxyphenylamino)-1-deoxy-D-ribulose-5-phosphate + ? = 1-C-(indol-3-yl)glycerol 3-phosphate + CO2 + H2O

0

1a53, 3D-view

4.1.1.48

1-(2-carboxyphenylamino)-1-deoxy-D-ribulose-5-phosphate + ? = 1-C-(indol-3-yl)glycerol 3-phosphate + CO2 + H2O

0

3t44, 3D-view

4.1.1.48

1-(2-carboxyphenylamino)-1-deoxy-D-ribulose-5-phosphate = indoleglycerol phosphate + CO2 + H2O

0

1a53, 3D-view

4.1.1.48

1-(2-carboxyphenylamino)-1-deoxy-D-ribulose-5-phosphate = indoleglycerol phosphate + CO2 + H2O

0

3t44, 3D-view

4.2.1.20

indole + D-glyceraldehyde 3-phosphate = indole-3-glycerol phosphate

5567, 5555, 5566

1a5b, 3D-view

4.2.1.20

indole + D-glyceraldehyde 3-phosphate = indole-3-glycerol phosphate

5567, 5555, 5566

1qoq, 3D-view

4.2.1.20

indole + D-glyceraldehyde 3-phosphate = indole-3-glycerol phosphate

5567, 5555, 5566

2rh9, 3D-view

4.2.1.20

indole + D-glyceraldehyde 3-phosphate = indole-3-glycerol phosphate

5567, 5555, 5566

2rhg, 3D-view

4.2.1.20

L-tryptophan + D-glyceraldehyde 3-phosphate + H2O = indole-3-glycerol phosphate + L-serine

5555

1a5b, 3D-view

4.2.1.20

L-tryptophan + D-glyceraldehyde 3-phosphate + H2O = indole-3-glycerol phosphate + L-serine

5555

1qoq, 3D-view

4.2.1.20

L-tryptophan + D-glyceraldehyde 3-phosphate + H2O = indole-3-glycerol phosphate + L-serine

5555

2rh9, 3D-view

4.2.1.20

L-tryptophan + D-glyceraldehyde 3-phosphate + H2O = indole-3-glycerol phosphate + L-serine

5555

2rhg, 3D-view

4.1.1.48

10 entries

4.2.1.20

8 entries

Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

6.1.1.21

-

374

-

3D Structure of Enzyme-Ligand-Complex (PDB) (42 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (42 entries)

EC NUMBER

ENZYME 3D STRUCTURE

4.1.1.48

1a53, 3D-view

4.1.1.48

3t44, 3D-view

4.1.1.48

1a53, 3D-view

4.1.1.48

3t44, 3D-view

4.1.1.48

1a53, 3D-view

4.1.1.48

3t44, 3D-view

4.1.1.48

1a53, 3D-view

4.1.1.48

3t44, 3D-view

4.1.1.48

1a53, 3D-view

4.1.1.48

3t44, 3D-view

4.1.1.48

1a53, 3D-view

4.1.1.48

3t44, 3D-view

4.1.1.48

1a53, 3D-view

4.1.1.48

3t44, 3D-view

4.2.1.20

1a5b, 3D-view

4.2.1.20

1qoq, 3D-view

4.2.1.20

2rh9, 3D-view

4.2.1.20

2rhg, 3D-view

4.2.1.20

1a5b, 3D-view

4.2.1.20

1qoq, 3D-view

4.2.1.20

2rh9, 3D-view

4.2.1.20

2rhg, 3D-view

4.2.1.20

1a5b, 3D-view

4.2.1.20

1qoq, 3D-view

4.2.1.20

2rh9, 3D-view

4.2.1.20

2rhg, 3D-view

4.2.1.20

1a5b, 3D-view

4.2.1.20

1qoq, 3D-view

4.2.1.20

2rh9, 3D-view

4.2.1.20

2rhg, 3D-view

4.2.1.20

1a5b, 3D-view

4.2.1.20

1qoq, 3D-view

4.2.1.20

2rh9, 3D-view

4.2.1.20

2rhg, 3D-view

4.2.1.20

1a5b, 3D-view

4.2.1.20

1qoq, 3D-view

4.2.1.20

2rh9, 3D-view

4.2.1.20

2rhg, 3D-view

4.2.1.20

1a5b, 3D-view

4.2.1.20

1qoq, 3D-view

4.2.1.20

2rh9, 3D-view

4.2.1.20

2rhg, 3D-view

4.1.1.48

14 entries

4.2.1.20

28 entries

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (3 results)

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Show Turnover Number (3 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

4.1.2.8

0.006

-

-

691511

4.1.2.8

2.3

-

-

670717

4.1.2.8

6.55

-

pH 8.0, 22°C

728444

4.1.2.8

3 entries

K_M Value (5 results)

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Show KM Value (5 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

4.1.2.8

0.096

-

pH 8.0, 22°C

728444

4.1.2.8

0.1

-

-

670717

4.1.2.8

0.458

-

-

691511

4.2.1.20

0.02

-

cosubstrate L-serine, pH 8.0, temperature not specified in the publication

747116

4.2.1.20

1.4

-

cosubstrate L-threonine, pH 8.0, temperature not specified in the publication

747116

4.1.2.8

3 entries

4.2.1.20

2 entries

References & Links

Literature References (66)

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Show Reference (66 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

374

6449959

Purification and characterization of histidyl-transfer RNA synthetase from Neurospora crassa

1980

Chen, C.C.; Somberg, E.W.

Biochim. Biophys. Acta

613

514-525

4592

2941339

A cloned tryptophan-synthesis gene from the ascomycete Cochliobolus heterostrophus functions in Escherichia coli, yeast and Aspergillus nidulans

1986

Turgeon, B.G.; MacRae, W.D.; Garber, R.C.; Fink, G.R.; Yoder, O.C.

Gene

42

79-88

4593

110789

Isolation and characterization of two tryptophan biosynthetic enzymes, indoleglycerol phosphate synthase and phosphoribosyl anthranilate isomerase, from Bacillus subtilis

1979

Hoch, S.O.

J. Bacteriol.

139

362-368

4594

348687

Tryptophan biosynthesis in Saccharomyces cerevisiae: control of the flux through the pathway

1978

Miozzari, G.; Niederberger, P.; Hutter, R.

J. Bacteriol.

134

48-59

4595

881418

Enzymes of the tryptophan synthetic pathway in Brevibacterium flavum

1977

Sugimoto, S.i.; Shiio, I.

J. Biochem.

81

823-833

4596

403178

Immunochemical comparison of phosphoribosylanthranilate isomerase-indoleglycerol phosphate synthetase among the enterobacteriaceae

1977

Reyers, G.R.; Rocha, V.

J. Bacteriol.

129

1448-1456

4597

769720

Free tryptophan pool and tryptophan biosynthetic enzymes in Saccharomyces cerevisiae

1976

Fantes, P.A.; Roberts, L.M.; Huetter, R.

Arch. Microbiol.

107

207-214

4598

766666

A rapid spectrophotofluorometric assay for indoleglycerol phosphate synthase

1975

Hankins, C.N.; Largen, M.; Mills, S.E.

Anal. Biochem.

69

510-517

4599

1116988

Tryptophan biosynthetic pathway in the Enterobacteriaceae: some physical properties of the enzymes

1975

Largen, M.; Belser, W.L.

J. Bacteriol.

121

239-249

4600

4698207

Tryptophan biosynthetic enzymes of Staphylococcus aureus

1973

Proctor, A.R.; Kloos, W.E.

J. Bacteriol.

114

169-177

4601

4559725

Partial characterization of phosphoribosyl transferase, phosphoribosyl anthranilate isomerase, and indole glycerol phosphate synthase from Serratia marcescens

1972

Potts, J.M.; Drapeau, G.R.

J. Bacteriol.

111

334-339

4602

5332729

Indole-3-glycerol phosphate synthetase of Escherichia coli, an enzyme of the tryptophan operon

1966

Creighton, T.E.; Yanofsky, C.

J. Biol. Chem.

241

4616-4624

4603

401810

A dimer of a single polypeptide chain catalyzes the terminal four reactions of the L-tryptophan pathway in Euglena gracilis

1977

Hankins, C.N.; Mills, S.E.

J. Biol. Chem.

252

235-239

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Links to other databases for (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate

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