Information on EC 1.1.1.14 - L-iditol 2-dehydrogenase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

EC NUMBER
COMMENTARY hide
1.1.1.14
-
RECOMMENDED NAME
GeneOntology No.
L-iditol 2-dehydrogenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
L-iditol + NAD+ = L-sorbose + NADH + H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
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reduction
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
D-sorbitol degradation I
-
-
degradation of sugar alcohols
-
-
Pentose and glucuronate interconversions
-
-
Fructose and mannose metabolism
-
-
Metabolic pathways
-
-
SYSTEMATIC NAME
IUBMB Comments
L-iditol:NAD+ 2-oxidoreductase
This enzyme is widely distributed and has been described in archaea, bacteria, yeast, plants and animals. It acts on a number of sugar alcohols, including (but not limited to) L-iditol, D-glucitol, D-xylitol, and D-galactitol. Enzymes from different organisms or tissues display different substrate specificity. The enzyme is specific to NAD+ and can not use NADP+.
CAS REGISTRY NUMBER
COMMENTARY hide
9028-21-1
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
acetic acid bacteria
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
(Kloeckera sp.) No. 2201
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Manually annotated by BRENDA team
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
Gluconobacter oxydans G624 (FERM BP-4415)
strain G624 (FERM BP-4415)
UniProt
Manually annotated by BRENDA team
strain IFO 3255
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Manually annotated by BRENDA team
strain IFO3257
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Manually annotated by BRENDA team
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
pheasant
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
japanese pear
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Manually annotated by BRENDA team
quail
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Automatic Mining of ENzyme DAta
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1064330 A+, 1133171 A+, 1163687 A+, 1337349 A+, 1425761 A+, 1448750 A+, 1454152 A+, 1458888 A+, 1464592 A+, 1468339 A+, 1468706 A+, 1485265 A+, 1573148 A+, 1573259 A+, 1573753 A+, 1647051 A+, 1661467 A+, 1675943 A+, 1682366 A+, 1682386 A+, 1682387 A+, 1682391 A+, 1682426 A+, 1682429 A+, 1682444 A+, 1682446 A+, 1682451 A+, 1682452 A+, 1682454 A+, 1682460 A+, 1682464 A+, 1682470 A+, 1682476 A+, 1682479 A+, 1682486 A+, 1682506 A+, 1682509 A+, 1682510 A+, 1682525 A+, 1682527 A+, 1682540 A+, 1682547 A+, 1682548 A+, 1682559 A+, 1682571 A+, 1682572 A+, 1682579 A+, 1682580 A+, 1682582 A+, 1682588 A+, 1682593 A+, 1682601 A+, 1682624 A+, 1682626 A+, 1682634 A+, 1682663 A+, 1682669 A+, 1682670 A+, 1682679 A+, 2239373 A+, 2239391 A+, 2470347 A+, 2551115 A+, 2585404 A+, 2749187 A+, 2749279 A+, 2749313 A+, 2749345 A+, 2749348 A+, 2749357 A+, 784560 A+, 789261 A+, 989795 A+, 989797 A+, 989799 A+, 989807 A+, 989808 A+, 989814 A+, 989817 A+, 989885 A+, 989889 A+, 989907 A+, 991434 A+, 1012991 A++, 1022830 A++, 1163665 A++, 1257446 A++, 1257779 A++, 1258659 A++, 1258672 A++, 1259605 A++, 1292898 A++, 1464272 A++, 1470777 A++, 1485365 A++, 1573226 A++, 1573377 A++, 1682368 A++, 1682373 A++, 1682376 A++, 1682378 A++, 1682379 A++, 1682385 A++, 1682392 A++, 1682395 A++, 1682406 A++, 1682408 A++, 1682415 A++, 1682431 A++, 1682435 A++, 1682437 A++, 1682439 A++, 1682441 A++, 1682445 A++, 1682448 A++, 1682449 A++, 1682488 A++, 1682494 A++, 1682503 A++, 1682513 A++, 1682514 A++, 1682530 A++, 1682538 A++, 1682539 A++, 1682545 A++, 1682554 A++, 1682567 A++, 1682568 A++, 1682576 A++, 1682587 A++, 1682605 A++, 1682623 A++, 1682630 A++, 1682631 A++, 2237740 A++, 2238361 A++, 2238377 A++, 2238378 A++, 2238381 A++, 2238383 A++, 2238384 A++, 2238387 A++, 2238389 A++, 2238390 A++, 2239297 A++, 2365308 A++, 2522164 A++, 2526437 A++, 2583967 A++, 2586078 A++, 2601165 A++, 2749278 A++, 2749285 A++, 2749291 A++, 2749303 A++, 2749304 A++, 2749327 A++, 2749344 A++, 2749355 A++, 2749363 A++, 2749381 A++, 668540 A++, 712190 A++, 989838 A++, 989843 A++, 991387 A++, 991503 A++, 1590880 A++, 1682353 A++, 1682365 A++, 1682369 A++, 1682398 A++, 1682402 A++, 1682412 A++, 1682413 A++, 1682419 A++, 1682440 A++, 1682442 A++, 1682453 A++, 1682459 A++, 1682462 A++, 1682463 A++, 1682484 A++, 1682501 A++, 1682532 A++, 1682533 A++, 1682537 A++, 1682541 A++, 1682558 A++, 1682561 A++, 1682583 A++, 1682585 A++, 1682628 A++, 2238358 A++, 2238359 A++, 2238363 A++, 2238374 A++, 2238375 A++, 2238376 A++, 2238379 A++, 2238380 A++, 2238386 A++, 2238388 A++, 2238392 A++, 2668581 A++, 2745257 A++, 2747298 A++, 2747315 A++, 2747680 A++, 2749282 A++, 2749289 A++, 2749295 A++, 2749297 A++, 2749301 A++, 2749302 A++, 2749305 A++, 2749307 A++, 2749309 A++, 2749314 A++, 2749315 A++, 2749321 A++, 2749323 A++, 2749334 A++, 2749339 A++, 2749346 A++, 2749361 A++, 285872 A++, 285875 A++, 285879 A++, 285887 A++, 989763 A++, 989764 A++, 989774 A++, 989829 A++, 989835 A++, 989836 A++, 989840 A++, 989857 A++, 989859 A++, 989862 A++, 989871 A++, 989875 A++, 989877 A++, 989878 A++, 989881 A++, 989891 A++, 989894 A++, 989897 A++, 991758 A++, 285876 A++++, 987088 A++++, 989762 A++++, 989782 A++++, 989820 A++++, 989827 A++++, 989839 A++++, 989842 A++++, 989848 A++++, 989851 A++++, 989858 A++++, 989868 A++++
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Automatic Mining of ENzyme DAta
strain Si4 (DSM8371)
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Manually annotated by BRENDA team
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
shrimp
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Automatic Mining of ENzyme DAta
squirrel
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
toad
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
yeasts
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Automatic Mining of ENzyme DAta
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
physiological function
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sorbitol dehydrogenase can convert sorbitol to fructose, which can then be metabolized via the glycolytic pathway in sperm to make ATP. Sorbitol can serve as an alternative energy source for sperm motility and protein tyrosine phosphorylation
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1,2-butanediol + NAD+
? + NADH + H+
show the reaction diagram
1,2-hexanediol + NAD+
? + NADH + H+
show the reaction diagram
3-deoxy-D-sorbitol + NAD+
? + NADH
show the reaction diagram
-
-
-
-
?
6-deoxy-D-sorbitol + NAD+
? + NADH
show the reaction diagram
-
nearly 2fold higher activity compared to D-sorbitol
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-
?
6-fluoro-D-sorbitol + NAD+
? + NADH
show the reaction diagram
-
over 2fold higher activity compared to D-sorbitol, best substrate
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-
?
D-adonitol + NAD+
D-ribulose + NADH
show the reaction diagram
-
-
-
-
?
D-arabinose + NADH
?
show the reaction diagram
D-arabitol + NAD(P)+
D-xylulose + NAD(P)H + H+
show the reaction diagram
D-arabitol + NAD+
?
show the reaction diagram
D-arabitol + NAD+
D-xylulose + NADH + H+
show the reaction diagram
D-fructose + NADH
?
show the reaction diagram
-
-
-
-
?
D-fructose + NADH + H+
D-sorbitol + NAD+
show the reaction diagram
D-galactitol + NAD+
D-tagatose + NADH
show the reaction diagram
D-galactitol + NAD+
D-tagatose + NADH + H+
show the reaction diagram
D-gluconate + NAD+
?
show the reaction diagram
-
low activity
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-
?
D-glucose + NADH
?
show the reaction diagram
-
low activity
-
-
?
D-glycero-D-gluco-heptitol + NAD+
?
show the reaction diagram
-
-
-
-
?
D-mannitol + NAD(P)+
D-fructose + NAD(P)H + H+
show the reaction diagram
D-mannitol + NAD+
?
show the reaction diagram
D-mannitol + NAD+
D-fructose + NADH + H+
show the reaction diagram
D-mannose + NADH
?
show the reaction diagram
-
low activity
-
-
?
D-psicose + NADH
?
show the reaction diagram
-
-
-
-
?
D-raffinose + NADH
?
show the reaction diagram
-
low activity
-
-
?
D-ribitol + NAD+
?
show the reaction diagram
D-ribose + NADH
?
show the reaction diagram
-
low activity
-
-
?
D-ribulose + NADH
?
show the reaction diagram
D-sorbitol + 2,6-dichlorophenolindophenol
L-sorbose + ?
show the reaction diagram
-
electron acceptor: i.e. DCIP
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-
?
D-sorbitol + NAD(P)+
L-sorbose + NAD(P)H + H+
show the reaction diagram
D-sorbitol + NAD+
? + NADH + H+
show the reaction diagram
-
-
-
-
?
D-sorbitol + NAD+
D-fructose + NADH + H+
show the reaction diagram
D-sorbitol + NAD+
L-sorbose + NADH + H+
show the reaction diagram
D-sorbitol + NADH + H+
D-fructose + NADH + H+
show the reaction diagram
D-sorbose + NADH
?
show the reaction diagram
-
low activity
-
-
?
D-tagatose + NADH
D-galactitol + NAD+
show the reaction diagram
D-xylitol + NAD+
?
show the reaction diagram
D-xylitol + NAD+
? + NADH + H+
show the reaction diagram
D-xylitol + NADP+
? + NADPH + H+
show the reaction diagram
NADP+ is not a cofactor for wild-type, but for a substrate-binding loop chimera
-
-
?
D-xylose + NADH
?
show the reaction diagram
D-xylulose + NADH
?
show the reaction diagram
erythritol + NAD+
?
show the reaction diagram
ethanol + NAD+
acetaldehyde + NADH
show the reaction diagram
glycerol + NAD+
?
show the reaction diagram
-
low activity
-
-
?
glycerol + NAD+
dihydroxyacetone + NADH
show the reaction diagram
L-arabitol + NAD+
?
show the reaction diagram
L-erythrulose + NADH
?
show the reaction diagram
-
-
-
-
?
L-iditol + NAD+
?
show the reaction diagram
L-rhamnose + NADH
?
show the reaction diagram
-
low activity
-
-
?
L-sorbose + NADH
?
show the reaction diagram
L-threitol + NAD+
?
show the reaction diagram
meso-erythritol + NAD+
erythrulose + NADH
show the reaction diagram
-
high activity
-
-
?
ribitol + NAD+
?
show the reaction diagram
60% of the activity with D-sorbitol
-
-
?
sorbitol + NAD+
D-fructose + NADH
show the reaction diagram
Xylitol + NAD+
?
show the reaction diagram
29% of the activity with D-sorbitol
-
-
?
xylitol + NAD+
D-xylulose + NADH + H+
show the reaction diagram
-
-
-
r
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
D-sorbitol + NAD+
D-fructose + NADH + H+
show the reaction diagram
D-sorbitol + NAD+
L-sorbose + NADH + H+
show the reaction diagram
D-sorbitol + NADH + H+
D-fructose + NADH + H+
show the reaction diagram
sorbitol + NAD+
D-fructose + NADH
show the reaction diagram
xylitol + NAD+
D-xylulose + NADH + H+
show the reaction diagram
-
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-
r
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADP+
NADPH
additional information
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Co2+
-
slightly activating
Fe3+
-
10 mM FeCl3 stimulates activity 2 fold
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(2S)-1-(3-thio-2-methylpropionyl)-L-proline
-
-
1,10-phenanthroline
1,2,3,4,5,6-cyclohexanehexolphosphoric acid
-
at pH 9.9
-
1,2-dithioethane
-
-
-
1,7-phenanthroline
-
-
1-thiobutane
-
-
1-thioglycol
-
-
1-thiosorbitol
-
-
2,2'-dipyridyl
-
-
2,3-Dimercaptopropanol
-
-
2,3-Dithiopropanol
-
-
2-hydroxybenzoic acid
-
at pH 9.9
2-hydroxymethyl-4-(4-N,N-dimethylaminosulfonyl-1-piperazino)pyrimidine
2-mercaptoethanol
-
-
2-methyl-4-(4-N,N-dimethylaminosulfonyl-1-piperazino)pyrimidine
i.e. SDI-157
2-methypropanoic acid amide
-
at pH 9.9
2-propylpentanoic acid
-
at pH 9.9
2-thiobutane
-
-
3,4-dihydroxyphenyl-1-hydroxyacetic acid
3,4-dihydroxyphenyl-ethanediol
-
at pH 7.4
3-hydroxy-4-methoxy-phenyl-1-hydroxy-acetic acid
-
at pH 7.4
4,4'-dipyridyl
-
-
4-hydroxy-3-methoxy-phenyl-1-hydroxy-acetic acid
-
at pH 7.4
4-hydroxy-3-methoxy-phenylacetic acid
-
at pH 7.4
4-hydroxy-3-methoxy-phenylethanediol
-
at pH 7.4
4-hydroxy-3-methoxy-phenylethyl alcohol
8-hydroxyquinoline
-
-
acetic acid amide
-
at pH 9.9
ADP
-
2 mM, 72% activity
AgNO3
Alrestatin
-
-
AMP
-
2 mM, 83% activity
ATP
-
2 mM, 54% activity
Ba(CH3COO)2
-
1 mM reduces activity to about 20%
Berberine
-
-
bis-diethylthiocarbamoyldisulfide
-
-
butanedioic acid
-
at pH 9.9
CdCl2
-
1 mM
Cibacron Blue 3G-A
-
-
CoCl2
CP-642,931
-
a potent and specific sorbitol dehydrogenase inhibitor, rmacokinetics, biomarker pharmacodynamics, and safety analysis, overview. The inhibitor is rapidly absorbed through the oral route and effectively inhibits SDH. However, the drug is not well tolerated due to adverse neuromuscular effects. The inhibitor alters the red blood cell sorbitol dehydrogenase activity after oral administration
-
CuSO4
cyanamide
cyanide
-
-
cysteamine
-
significant only at pH 9.9
cysteine
D-fructose
D-sorbitol
-
above 49 mM, substrate inhibition
Decanoic acid
-
at pH 9.9
diethyldicarbonate
-
-
Diethylthiocarbamate
Disulfiram
-
-
dithioerythritol
-
protection at low concentration, inhibition at high concentration, 100 mM
dithiothreitol
DL-2-bromosuccinate
-
1 mM
DL-2-thiovaline
-
-
DTT
-
competitive and noncompetitive with respect to D-sorbitol and NAD+, respectively
Eriochrome Black T
-
-
ethanedioic acid
-
at pH 9.9
Fe2+
-
complete inhibition at 0.91 mM
FeSO4
-
1 mM
glutathione
-
-
HgCl2
ICI 171071
-
-
ICI 222155
-
-
imidazole
-
-
iodoacetamide
-
NADH 0.4 mM protects
iodoacetate
Isonicotinic acid hydrazide
-
-
KCl
-
0.1 M, inactivation
Mg2+
-
slightly inhibitory
MgCl2
MgSO4
-
1 mM
Mn2+
-
slightly inhibitory
monoiodoacetate
-
75% inhibition at 1.79 mM
N-bromosuccinimide
-
-
N-ethylmaleimide
-
1 mM
NiCl2
o-phenanthroline
-
-
p-chloromercuribenzoate
p-hydroxymercuribenzoate
-
-
Pb(CH3COO)2
-
-
Penicillamine
-
weak inhibition
Ponalrestat
-
-
propanedioic acid
-
at pH 9.9
pyrazole
quercetin
quinine x HCl
-
slightly inhibitory, 25% inhibition at 1.79 mM
Semicarbazide
-
10 mM
thioacetate
-
at pH 9.9
Thiocyanate
Thiourea
-
at pH 9.9
Tolrestat
-
-
Urea
-
at pH 9.9
Valproic acid
-
weak inhibition
ZnSO4
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(R)-(-)-2-octanol
-
at pH 9.9
(S)-(+)-2-octanol
-
at pH 9.9
1-Hexanol
-
-
1-Octanol
-
-
2,2,2-tribromoethanol
-
-
2,2,2-trichloroethanol
-
-
2,2,2-Trifluoroethanol
-
-
2-monobromoethanol
-
-
2-monochloroethanol
-
-
2-monofluoroethanol
-
-
cysteine
-
fructose reduction at pH 7.4, inhibits at pH 9.0
D-sorbitol
-
at high concentration
dithiothreitol
-
1 mM 24% stimulation
haloalcohols
-
at high concentration
-
Semicarbazide
-
1 mM
Sodium azide
-
10 mM stimulates 2fold
sodium taurodeoxycholate
-
-
ZnSO4
additional information
-
enzyme needs product, i.e. SldB, of upstream gene sldB, encoding a hydrophobic polypeptide, for activity, the polypeptide might be a chaperone-like component that signals processing and folding of the enzyme to give the active enzyme form
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
15.5
2-deoxy-D-sorbitol
1.9
3-deoxy-D-sorbitol
-
-
15.5
3-fluoro-D-sorbitol
-
-
26.4
4-deoxy-D-sorbitol
-
-
11.7
4-fluoro-D-sorbitol
-
-
0.48
6-deoxy-D-sorbitol
-
-
0.74
6-fluoro-D-sorbitol
-
-
1 - 1500
D-fructose
1.5 - 500
D-galactitol
6.2 - 9.1
D-glucitol
16 - 555
D-mannitol
1.3 - 125
D-ribitol
34 - 260
D-ribulose
0.0032 - 785
D-sorbitol
10 - 13
D-tagatose
0.17 - 37
D-xylitol
1
D-xylulose
-
-
20
L-arabitol
-
-
25
L-erythrulose
-
-
9 - 20
L-Iditol
110 - 800
L-sorbose
268
L-Threitol
-
-
0.041 - 0.6
NAD+
0.007 - 0.28
NADH
0.41
NADP+
substrate-binding loop chimera plus mutation D55N, pH 9.0, temperature not specified in the publication
additional information
additional information
-
kinetic mechanism
-