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Ligand isoascorbic acid

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

Substrate in Enzyme-catalyzed Reactions (1 result)

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Show Substrate (1 entry)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.19

alpha-cyclodextrin + isoascorbic acid = L-isoascorbic acid-2-O-alpha-D-glucoside + L-isoascorbic acid-2-O-alpha-D-oligoglucoside

488841

-

Product in Enzyme-catalyzed Reactions (4 results)

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Show Product (4 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.10.3.3

D-isoascorbate + O2 = 2-dehydroisoascorbate + H2O

0

-

1.10.3.3

D-isoascorbic acid + O2 = 2-dehydroisoascorbate + H2O

439938, 439889, 439931, 439932

-

1.10.3.3

2 entries

1.6.5.4

NADH + monodehydroisoascorbate = NAD+ + isoascorbate

0

-

1.8.5.1

GSH + isodehydroascorbate = GSSG + isoascorbate

0

-

Enzyme Cofactor/Cosubstrate (1 result)

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Show Cofactor (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.14.17.4

may substitute for ascorbate, 75% of the efficiency of ascorbate

716448

-

Activator in Enzyme-catalyzed Reactions (4 results)

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Show Activating Compound (4 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.14.11.1

increase of activity

439283

-

1.14.11.11

partial activation

439275

-

1.14.13.81

prevents degradation of tetrapyrroles by reactive oxygen species

636329

-

1.14.15.20

-

739342

-

Inhibitor in Enzyme-catalyzed Reactions (8 results)

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Show Inhibitors (8 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.179

competitive inhibitor

684150

-

1.10.3.1

-

745732

-

1.10.3.1

1 mM, 99% inhibition

440427

-

1.10.3.1

1 mM, complete inhibition of isoenzymes Ia, Ib and II

440441

-

1.10.3.1

3 entries

1.10.3.2

-

396346

-

1.3.1.20

-

286128, 349254, 684150

2poq, 3D-view

1.3.1.20

competitive inhibitor

684150, 686023

2poq, 3D-view

1.3.1.20

inhibits dihydrodiol and D-xylose dehydrogenase activity

286128

2poq, 3D-view

1.3.1.20

3 entries

3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (1 entry)

EC NUMBER

ENZYME 3D STRUCTURE

1.3.1.20

2poq, 3D-view

Enzyme Kinetic Parameters

IC₅₀ Value (13 results)

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Show IC50 Value (13 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

1.3.1.20

0.037

-

wild type enzyme, in 25 mM Tris-HCl pH 7.5, at 25°C

684150

1.3.1.20

0.038

-

determined in the camphorquinone reduction, inhibitor is uncompetitive with respect to camphorquinone

684150

1.3.1.20

0.038

-

mutant enzyme W254Y, in 25 mM Tris-HCl pH 7.5, at 25°C

684150

1.3.1.20

0.038

-

mutant W254Y

684150

1.3.1.20

0.043

-

-

686023

1.3.1.20

0.066

-

mutant enzyme W254A, in 25 mM Tris-HCl pH 7.5, at 25°C

684150

1.3.1.20

0.066

-

mutant W254A

684150

1.3.1.20

0.288

-

mutant enzyme F154A, in 25 mM Tris-HCl pH 7.5, at 25°C

684150

1.3.1.20

0.288

-

mutant F154A

684150

1.3.1.20

3.94

-

mutant enzyme F154A, in 25 mM Tris-HCl pH 7.5, at 25°C

684150

1.3.1.20

3.94

-

mutant F279A

684150

1.3.1.20

4.176

-

mutant enzyme W125Y, in 25 mM Tris-HCl pH 7.5, at 25°C

684150

1.3.1.20

4.176

-

mutant W125Y

684150

1.3.1.20

13 entries

References & Links

Literature References (18)

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Show Reference (18 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

286128

11306093

Identity of dimeric dihydrodiol dehydrogenase as NADP+-dependent D-xylose dehydrogenase in pig liver

2001

Aoki, S.; Ishikura, S.; Asada, Y.; Usami, N.; Hara, A.

Chem. Biol. Interact.

130-132

775-784

349254

7852295

Purification and characterization of dimeric dihydrodiol dehydrogenase from dog liver

1994

Sato, K.; Nakanishi, M.; Deyashiki, Y.; Hara, A.; Matsuura, K.; Ohya, I.

J. Biochem.

116

711-717

396346

-

Characterization of polyphenol oxidase from Chaetomium thermophile, a thermophilic fungus

1988

Ishigami, T.; Hirose, Y.; Yamada, Y.

J. Gen. Appl. Microbiol.

34

401-407

439275

3569262

Purification and characterization of hyoscyamine 6 beta-hydroxylase from root cultures of Hyoscyamus niger L. Hydroxylase and epoxidase activities in the enzyme preparation

1987

Hashimoto, T.; Yamada, Y.

Eur. J. Biochem.

164

277-285

439283

4396068

Cofactor requirements of gamma-butyrobetaine hydroxylase from rat liver

1970

Lindstedt, G.; Lindstedt, S.

J. Biol. Chem.

245

4178-4186

439889

-

Ascorbic acid oxidase

1963

Stark, G.R.; Dawson, C.R.

The Enzymes, 2nd Ed (Boyer, P. D. , Lardy, H. , Myrbäck, K. , eds. )

8

297-311

439931

7945293

Substrate specificity of ascorbate oxidase: unexpected similarity to the reduction site of dopamine beta-monooxygenase

1994

Wimalasena, K.; Dharmasena, S.

Biochem. Biophys. Res. Commun.

203

1471-1476

439932

-

Properties of ascorbate oxidase produced by Acremonium sp. HI-25

1995

Itoh, H.; Hirota, A.; Hirayama, K.; Shin, T.; Murao, S.

Biosci. Biotechnol. Biochem.

59

1052-1056

439938

100178558

Purification and characterisation of ascorbate oxidase from flour and immature wheat kernels.

1999

Every, D.

J. Cereal Sci.

30

245-254

440427

-

Properties of polyphenol oxidase from Alternaria tenuis

1979

Motoda, S.

J. Ferment. Technol.

57

79-85

440441

-

Purification and characterization of polyphenol oxidase from callus cultures of Portulaca grandiflora

2002

Yamamoto, K.; Yoshitama, K.; Teramoto, S.

Plant Biotechnol.

19

95-101

488841

1829640

Characterization of Bacillus stearothermophilus cyclodextrin glucanotransferase in ascorbic acid 2-O-alpha-glucoside formation

1991

Tanaka, M.; Muto, N.; Yamamoto, I.

Biochim. Biophys. Acta

1078

127-132

636329

12226378

The chlorophyll biosynthetic enzyme Mg-protoporphyrin IX monomethyl ester (oxidative) cyclase. Characterization and partial purification from Chlamydomonas reinhardtii and Synechocystis sp. PCC 6803

1996

Bollivar, D.W.; Beale, S.I.

Plant Physiol.

112

105-114

684150

18453689

Structure of monkey dimeric dihydrodiol dehydrogenase in complex with isoascorbic acid

2008

Carbone, V.; Sumii, R.; Ishikura, S.; Asada, Y.; Hara, A.; El-Kabbani, O.

Acta Crystallogr. Sect. D

64

532-542

686023

18264804

Structural and functional features of dimeric dihydrodiol dehydrogenase

2008

Carbone, V.; Hara, A.; El-Kabbani, O.

Cell. Mol. Life Sci.

65

1464-1474

716448

-

Characterization of the ethylene-forming enzyme partially purified from melon

1992

Smith, J.; Ververidis, P.; John, P.

Phytochemistry

31

1485-1494

739342

12481078

Expression and biochemical properties of a ferredoxin-dependent heme oxygenase required for phytochrome chromophore synthesis

2002

Muramoto, T.; Tsurui, N.; Terry, M.; Yokota, A.; Kohchi, T.

Plant Physiol.

130

1958-1966

745732

-

Characterization of polyphenol oxidase extracted from white radish

2014

Hua, Y.; Shen, G.; Liu, D.

Mod. Food Sci. Technol.

30

69-73

Links to other databases for isoascorbic acid

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Show Links (1 entry)

ChEBI

PubChem