4.1.2.55: 2-dehydro-3-deoxy-phosphogluconate/2-dehydro-3-deoxy-6-phosphogalactonate aldolase
This is an abbreviated version!
For detailed information about 2-dehydro-3-deoxy-phosphogluconate/2-dehydro-3-deoxy-6-phosphogalactonate aldolase, go to the full flat file.
Word Map on EC 4.1.2.55
-
4.1.2.55
-
sulfolobus
-
solfataricus
-
entner-doudoroff
-
hyperthermophilic
-
dehydratase
-
non-phosphorylative
-
aldolases
-
archaeon
-
galactose
-
n-acetylneuraminate
-
stereochemical
-
thermoacidophilic
-
nonphosphorylated
-
picrophilus
-
acidocaldarius
-
dhdps
-
stereoselectivity
-
dihydrodipicolinate
-
torridus
-
synthesis
- 4.1.2.55
-
sulfolobus
- solfataricus
-
entner-doudoroff
-
hyperthermophilic
- dehydratase
-
non-phosphorylative
- aldolases
- archaeon
- galactose
- n-acetylneuraminate
-
stereochemical
-
thermoacidophilic
-
nonphosphorylated
-
picrophilus
- acidocaldarius
- dhdps
-
stereoselectivity
- dihydrodipicolinate
- torridus
- synthesis
Reaction
Synonyms
2-keto-3-deoxy-6-phosphogluconate aldolase, 2-keto-3-deoxygluconate aldolase, KD(P)G-aldolase, KDG aldolase, KDG-aldolase, KDGA, SacKdgA
ECTree
4.1.2.55 2-dehydro-3-deoxy-phosphogluconate/2-dehydro-3-deoxy-6-phosphogalactonate aldolaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 4.1.2.55 - 2-dehydro-3-deoxy-phosphogluconate/2-dehydro-3-deoxy-6-phosphogalactonate aldolase
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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
2-dehydro-3-deoxy-6-phospho-D-gluconate
pyruvate + D-glyceraldehyde 3-phosphate
preferred substrate
-
-
?
pyruvate + D-erythrose
(4S,5S,6R)-4,5,6,7-tetrahydroxy-2-oxoheptanoate
-
formation of (4S,5S,6R)-4,5,6,7-tetrahydroxy-2-oxoheptanoate and (4S,5S,6R)-4,5,6,7-tetrahydroxy-2-oxoheptanoate in the ratio 35:65
-
-
?
pyruvate + D-glyceraldehyde
3-deoxy-D-erythro-hex-2-ulosonate
-
formation of 3-deoxy-D-erythro-hex-2-ulosonate and 3-deoxy-D-threo-hex-2-ulosonate in the ratio 45:55
-
-
?
pyruvate + D-glyceraldehyde
3-deoxy-D-threo-hex-2-ulosonate
-
formation of 3-deoxy-D-erythro-hex-2-ulosonate and 3-deoxy-D-threo-hex-2-ulosonate in the ratio 45:55
-
-
?
pyruvate + D-glyceraldehyde 3-phosphate
2-dehydro-3-deoxy-D-galactonate 6-phosphate
higher activity with D-glyceraldehyde 3-phosphate compared to D-glyceraldehyde
-
-
r
pyruvate + D-glyceraldehyde acetonide
3-deoxy-5,6-O-(1-methylethylidene)-D-erythro-hex-2-ulosonate
-
highly stereoselective formation of 3-deoxy-5,6-O-(1-methylethylidene)-D-erythro-hex-2-ulosonate in 92% diastereomeric excess
-
-
?
pyruvate + D-threose
(4R,5R,6R)-4,5,6,7-tetrahydroxy-2-oxoheptanoate
-
formation of (4S,5R,6R)-4,5,6,7-tetrahydroxy-2-oxoheptanoate and (4R,5R,6R)-4,5,6,7-tetrahydroxy-2-oxoheptanoate in the ratio 40:60
-
-
?
pyruvate + D-threose
(4S,5R,6R)-4,5,6,7-tetrahydroxy-2-oxoheptanoate
-
formation of (4S,5R,6R)-4,5,6,7-tetrahydroxy-2-oxoheptanoate and (4R,5R,6R)-4,5,6,7-tetrahydroxy-2-oxoheptanoate in the ratio 40:60
-
-
?
pyruvate + L-erythrose
(4R,5R,6S)-4,5,6,7-tetrahydroxy-2-oxoheptanoate
-
formation of (4S,5R,6S)-4,5,6,7-tetrahydroxy-2-oxoheptanoate and (4R,5R,6S)-4,5,6,7-tetrahydroxy-2-oxoheptanoate in the ratio 60:40
-
-
?
pyruvate + L-erythrose
(4S,5R,6S)-4,5,6,7-tetrahydroxy-2-oxoheptanoate
-
formation of (4S,5R,6S)-4,5,6,7-tetrahydroxy-2-oxoheptanoate and (4R,5R,6S)-4,5,6,7-tetrahydroxy-2-oxoheptanoate in the ratio 60:40
-
-
?
pyruvate + L-glyceraldehyde
2-dehydro-3-deoxy-L-galactonate
-
condensation of pyruvate with L-glyceraldehyde proceeds with no stereocontrol, yielding a 53:47 diastereoisomeric mixture of 2-dehydro-3-deoxy-L-gluconate (anti-(4S,5R)-3-deoxy-2-hexulosonate) and 2-dehydro-3-deoxy-L-galactonate (syn-(4S,5S)-3-deoxy-2-hexulosonate)
-
-
?
pyruvate + L-glyceraldehyde
2-dehydro-3-deoxy-L-gluconate
-
condensation of pyruvate with L-glyceraldehyde proceeds with no stereocontrol, yielding a 53:47 diastereoisomeric mixture of 2-dehydro-3-deoxy-L-gluconate (anti-(4S,5R)-3-deoxy-2-hexulosonate) and 2-dehydro-3-deoxy-L-galactonate (syn-(4S,5S)-3-deoxy-2-hexulosonate)
-
-
?
pyruvate + L-glyceraldehyde
3-deoxy-D-erythro-hex-2-ulosonate
-
formation of 3-deoxy-L-threo-hex-2-ulosonate and 3-deoxy-L-erythro-hex-2-ulosonate in the ratio 50:50
-
-
?
pyruvate + L-glyceraldehyde
3-deoxy-D-threo-hex-2-ulosonate
-
formation of 3-deoxy-L-threo-hex-2-ulosonate and 3-deoxy-L-erythro-hex-2-ulosonate in the ratio 50:50
-
-
?
pyruvate + L-glyceraldehyde acetonide
3-deoxy-5,6-O-(1-methylethylidene)-L-threo-hex-2-ulosonate
-
highly stereoselective formation of 3-deoxy-5,6-O-(1-methylethylidene)-L-threo-hex-2-ulosonate in 94% diastereomeric excess
-
-
?
pyruvate + L-threose
(4R,5S,6S)-4,5,6,7-tetrahydroxy-2-oxoheptanoate
-
formation of (4S,5S,6S)-4,5,6,7-tetrahydroxy-2-oxoheptanoate and (4R,5S,6S)-4,5,6,7-tetrahydroxy-2-oxoheptanoate in the ratio 90:10
-
-
?
pyruvate + L-threose
(4S,5S,6S)-4,5,6,7-tetrahydroxy-2-oxoheptanoate
-
formation of (4S,5S,6S)-4,5,6,7-tetrahydroxy-2-oxoheptanoate and (4R,5S,6S)-4,5,6,7-tetrahydroxy-2-oxoheptanoate in the ratio 90:10
-
-
?
2-dehydro-3-deoxy-D-galactonate
pyruvate + D-glyceraldehyde
-
-
-
-
?
2-dehydro-3-deoxy-D-galactonate
pyruvate + D-glyceraldehyde
-
-
-
?
2-dehydro-3-deoxy-D-galactonate
pyruvate + D-glyceraldehyde
key enzyme in both the non- and the semi-phosphorylative EntnerDoudoroff pathway
-
-
?
2-dehydro-3-deoxy-D-galactonate
pyruvate + D-glyceraldehyde
the same enzyme is responsible for the catabolism of both glucose and galactose
-
-
?
2-dehydro-3-deoxy-D-galactonate
pyruvate + D-glyceraldehyde
catalytic efficiency (kcat/KM) is 295fold lower compared to 2-dehydro-3-deoxy-D-galactonate 6-phosphate
-
-
?
2-dehydro-3-deoxy-D-galactonate
pyruvate + D-glyceraldehyde
lack of stereoselectivity in the condensation reaction of pyruvate and D-glyceraldehyde, forming a mixture of 2-dehydro-3-deoxy-D-gluconate and 2-dehydro-3-deoxy-D-galactonate
-
-
r
2-dehydro-3-deoxy-D-galactonate
pyruvate + D-glyceraldehyde
key enzyme in both the non- and the semi-phosphorylative EntnerDoudoroff pathway
-
-
?
2-dehydro-3-deoxy-D-galactonate
pyruvate + D-glyceraldehyde
-
key enzyme in both the non- and the semi-phosphorylative EntnerDoudoroff pathway
-
-
?
2-dehydro-3-deoxy-D-galactonate 6-phosphate
pyruvate + D-glyceraldehyde 3-phosphate
-
-
-
?
2-dehydro-3-deoxy-D-galactonate 6-phosphate
pyruvate + D-glyceraldehyde 3-phosphate
key enzyme in both the non- and the semi-phosphorylative EntnerDoudoroff pathway
-
-
?
2-dehydro-3-deoxy-D-galactonate 6-phosphate
pyruvate + D-glyceraldehyde 3-phosphate
catalytic efficiency (kcat/KM) is 295fold higher compared to 2-dehydro-3-deoxy-D-galactonate
-
-
?
2-dehydro-3-deoxy-D-galactonate 6-phosphate
pyruvate + D-glyceraldehyde 3-phosphate
key enzyme in both the non- and the semi-phosphorylative EntnerDoudoroff pathway
-
-
?
2-dehydro-3-deoxy-D-galactonate 6-phosphate
pyruvate + D-glyceraldehyde 3-phosphate
-
key enzyme in both the non- and the semi-phosphorylative EntnerDoudoroff pathway
-
-
?
2-dehydro-3-deoxy-D-gluconate
pyruvate + D-glyceraldehyde
-
-
-
-
?
2-dehydro-3-deoxy-D-gluconate
pyruvate + D-glyceraldehyde
-
-
-
?
2-dehydro-3-deoxy-D-gluconate
pyruvate + D-glyceraldehyde
comparison of the catalytic efficiency (kcat/KM) for 2-dehydro-3-deoxy-D-gluconate (1.1 mM/s) and 2-dehydro-3-deoxy-D-gluconate 6-phosphate (643 mM/s) suggests that cleavage of the phosphorylated substrate would be significantly favoured in a situation where both compounds are present. If the 2-dehydro-3-deoxy-D-gluconate kinase is present and active then central metabolism will occur via the part-phosphorylative route.The Km of the kinase for ATP of 2.8 mM is high compared to the likely intracellular concentration, and it is possible that the non-phosphorylative pathway would be favoured under starvation conditions, which could produce pyruvate to allow the citric acid cycle to function without ATP input. regardless of whether Sulfolobus solfataricus uses the part-phosphorylative or the non-phosphorylative Entner-Doudoroff pathway, then the same enzymes can be used for the metabolism of glucose and its C4 epimer galactose
-
-
?
2-dehydro-3-deoxy-D-gluconate
pyruvate + D-glyceraldehyde
key enzyme in both the non- and the semi-phosphorylative EntnerDoudoroff pathway
-
-
?
2-dehydro-3-deoxy-D-gluconate
pyruvate + D-glyceraldehyde
the same enzyme is responsible for the catabolism of both glucose and galactose
-
-
?
2-dehydro-3-deoxy-D-gluconate
pyruvate + D-glyceraldehyde
catalytic efficiency (kcat/KM) is 580fold lower compared to 2-dehydro-3-deoxy-D-gluconate 6-phosphate
-
-
?
2-dehydro-3-deoxy-D-gluconate
pyruvate + D-glyceraldehyde
lack of stereoselectivity in the condensation reaction of pyruvate and D-glyceraldehyde, forming a mixture of 2-dehydro-3-deoxy-D-gluconate and 2-dehydro-3-deoxy-D-galactonate
-
-
r
2-dehydro-3-deoxy-D-gluconate
pyruvate + D-glyceraldehyde
key enzyme in both the non- and the semi-phosphorylative EntnerDoudoroff pathway
-
-
?
2-dehydro-3-deoxy-D-gluconate
pyruvate + D-glyceraldehyde
-
key enzyme in both the non- and the semi-phosphorylative EntnerDoudoroff pathway
-
-
?
2-dehydro-3-deoxy-D-gluconate 6-phosphate
pyruvate + D-glyceraldehyde 3-phosphate
-
-
-
?
2-dehydro-3-deoxy-D-gluconate 6-phosphate
pyruvate + D-glyceraldehyde 3-phosphate
key enzyme in both the non- and the semi-phosphorylative EntnerDoudoroff pathway
-
-
?
2-dehydro-3-deoxy-D-gluconate 6-phosphate
pyruvate + D-glyceraldehyde 3-phosphate
catalytic efficiency (kcat/KM) is 580fold higher compared to 2-dehydro-3-deoxy-D-gluconate
-
-
?
2-dehydro-3-deoxy-D-gluconate 6-phosphate
pyruvate + D-glyceraldehyde 3-phosphate
key enzyme in both the non- and the semi-phosphorylative EntnerDoudoroff pathway
-
-
?
2-dehydro-3-deoxy-D-gluconate 6-phosphate
pyruvate + D-glyceraldehyde 3-phosphate
-
key enzyme in both the non- and the semi-phosphorylative EntnerDoudoroff pathway
-
-
?
2-dehydro-3-deoxy-D-xylonate
pyruvate + glycolaldehyde
non-phosphorylative Entner-Doudoroff pathway for catabolism of D-xylose and L-arabinose
-
-
?
2-dehydro-3-deoxy-D-xylonate
pyruvate + glycolaldehyde
since the substrate is not commercially available a coupled assay is carried out
-
-
r
2-dehydro-3-deoxy-D-xylonate
pyruvate + glycolaldehyde
non-phosphorylative Entner-Doudoroff pathway for catabolism of D-xylose and L-arabinose
-
-
?
2-dehydro-3-deoxy-D-xylonate
pyruvate + glycolaldehyde
since the substrate is not commercially available a coupled assay is carried out
-
-
r
2-dehydro-3-deoxy-L-arabinonate
pyruvate + glycolaldehyde
-
-
-
-
?
2-dehydro-3-deoxy-L-arabinonate
pyruvate + glycolaldehyde
non-phosphorylative Entner-Doudoroff pathway for catabolism of D-xylose and L-arabinose
-
-
?
2-dehydro-3-deoxy-L-arabinonate
pyruvate + glycolaldehyde
since the substrate is not commercially available a coupled assay is carried out
-
-
r
2-dehydro-3-deoxy-L-arabinonate
pyruvate + glycolaldehyde
non-phosphorylative Entner-Doudoroff pathway for catabolism of D-xylose and L-arabinose
-
-
?
2-dehydro-3-deoxy-L-arabinonate
pyruvate + glycolaldehyde
since the substrate is not commercially available a coupled assay is carried out
-
-
r
pyruvate + D-glyceraldehyde
2-dehydro-3-deoxy-D-galactonate
the enzyme exhibits poor diastereocontrol in many of its aldol reactions, including the reaction of its natural substrates, pyruvate and D-glyceraldehyde, which afford a 55:45 mixture of D-2-keto-3-deoxygluconate and D-2-keto-3-deoxy-galactonate
-
-
r
pyruvate + D-glyceraldehyde
2-dehydro-3-deoxy-D-galactonate
the enzyme shows a lack of facial selectivity, yielding approximately equal quantities of 2-keto-3-deoxy-D-gluconate and 2-keto-3-deoxy-D-galactonate
-
-
r
pyruvate + D-glyceraldehyde
2-dehydro-3-deoxy-D-galactonate
-
the enzyme exhibits no diastereocontrol for the aldol condensation of its natural substrates pyruvate and D-glyceraldehyde and gives a 50:50 mixture of 2-dehydro-3-deoxy-D-gluconate (anti-(4S,5R)-3-deoxy-2-hexulosonate) and 2-dehydro-3-deoxy-D-galactobate (syn-(4R,5R)-3-deoxy-2-hexulosonate)
-
-
?
pyruvate + D-glyceraldehyde
2-dehydro-3-deoxy-D-galactonate
-
-
-
?
pyruvate + D-glyceraldehyde
2-dehydro-3-deoxy-D-galactonate
higher activity with D-glyceraldehyde 3-phosphate compared to D-glyceraldehyde. The enzyme forms a mixture of D-2-keto-3-deoxygluconate and D-2-keto-3-deoxy-galactonate
-
-
r
pyruvate + D-glyceraldehyde
2-dehydro-3-deoxy-D-galactonate
higher activity with D-glyceraldehyde 3-phosphate compared to D-glyceraldehyde. The enzyme forms a mixture of D-2-dehydro-3-deoxygluconate and D-2-dehydro-3-deoxy-galactonate
-
-
r
pyruvate + D-glyceraldehyde
2-dehydro-3-deoxy-D-gluconate
-
-
-
r
pyruvate + D-glyceraldehyde
2-dehydro-3-deoxy-D-gluconate
no activity could be detected with D-glyceraldehyde 3-phosphate as substrate in place of glyceraldehyde or with the pyruvate analogues beta-hydroxypyruvate and alpha-ketobutyrate. Studies by other groups reveal activity with D-glyceraldehyde 3-phosphate
-
-
r
pyruvate + D-glyceraldehyde
2-dehydro-3-deoxy-D-gluconate
the enzyme exhibits poor diastereocontrol in many of its aldol reactions, including the reaction of its natural substrates, pyruvate and D-glyceraldehyde, which afford a 55:45 mixture of D-2-keto-3-deoxygluconate and D-2-keto-3-deoxy-galactonate
-
-
r
pyruvate + D-glyceraldehyde
2-dehydro-3-deoxy-D-gluconate
the enzyme shows a lack of facial selectivity, yielding approximately equal quantities of 2-keto-3-deoxy-D-gluconate and 2-keto-3-deoxy-D-galactonate
-
-
r
pyruvate + D-glyceraldehyde
2-dehydro-3-deoxy-D-gluconate
-
the enzyme exhibits no diastereocontrol for the aldol condensation of its natural substrates pyruvate and D-glyceraldehyde and gives a 50:50 mixture of 2-dehydro-3-deoxy-D-gluconate (anti-(4S,5R)-3-deoxy-2-hexulosonate) and 2-dehydro-3-deoxy-D-galactobate (syn-(4R,5R)-3-deoxy-2-hexulosonate)
-
-
?
pyruvate + D-glyceraldehyde
2-dehydro-3-deoxy-D-gluconate
no activity could be detected with D-glyceraldehyde 3-phosphate as substrate in place of glyceraldehyde or with the pyruvate analogues beta-hydroxypyruvate and alpha-ketobutyrate. Studies by other groups reveal activity with D-glyceraldehyde 3-phosphate
-
-
r
pyruvate + D-glyceraldehyde
2-dehydro-3-deoxy-D-gluconate
-
-
-
r
pyruvate + D-glyceraldehyde
2-dehydro-3-deoxy-D-gluconate
-
-
-
?
pyruvate + D-glyceraldehyde
2-dehydro-3-deoxy-D-gluconate
higher activity with D-glyceraldehyde 3-phosphate compared to D-glyceraldehyde. The enzyme forms a mixture of D-2-keto-3-deoxygluconate and D-2-keto-3-deoxy-galactonate
-
-
r
pyruvate + D-glyceraldehyde
2-dehydro-3-deoxy-D-gluconate
higher activity with D-glyceraldehyde 3-phosphate compared to D-glyceraldehyde. The enzyme forms a mixture of D-2-dehydro-3-deoxygluconate and D-2-dehydro-3-deoxy-galactonate
-
-
r
pyruvate + D-glyceraldehyde 3-phosphate
2-dehydro-3-deoxy-D-gluconate 6-phosphate
-
-
-
r
pyruvate + D-glyceraldehyde 3-phosphate
2-dehydro-3-deoxy-D-gluconate 6-phosphate
higher activity with D-glyceraldehyde 3-phosphate compared to D-glyceraldehyde
-
-
r
pyruvate + D-glyceraldehyde 3-phosphate
2-dehydro-3-deoxy-D-gluconate 6-phosphate
-
-
-
-
r
pyruvate + glycolaldehyde
2-dehydro-3-deoxy-D-xylonate
-
-
-
r
pyruvate + glycolaldehyde
2-dehydro-3-deoxy-D-xylonate
-
-
-
r
pyruvate + glycolaldehyde
2-dehydro-3-deoxy-D-xylonate
-
-
-
r
pyruvate + glycolaldehyde
2-dehydro-3-deoxy-L-arabinonate
-
-
-
r
pyruvate + glycolaldehyde
2-dehydro-3-deoxy-L-arabinonate
-
-
-
r
additional information
?
-
-
the enzyme displays a relatively broad specificity profile towards nonphosphorylated aldehydes
-
-
?
additional information
?
-
the enzyme shows strict requirement for pyruvate
-
-
?
