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Information on EC 1.1.1.412 - 2-alkyl-3-oxoalkanoate reductase
for references in articles please use BRENDA:EC1.1.1.412
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EC Tree 1 Oxidoreductases
1.1 Acting on the CH-OH group of donors
1.1.1 With NAD+ or NADP+ as acceptor
1.1.1.412 2-alkyl-3-oxoalkanoate reductase
IUBMB Comments
The enzyme, found in certain bacterial species, is part of a pathway for the production of olefins.
The enzyme appears in viruses and cellular organisms
Reaction Schemes
showa (2R,3S)-2-alkyl-3-hydroxyalkanoate
+
=
an (R)-2-alkyl-3-oxoalkanoate
+
+
Synonyms
2-alkyl-3-ketoalkanoic acid reductase, oleD, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
2-alkyl-3-ketoalkanoic acid reductase
oleD
oleD
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a (2R,3S)-2-alkyl-3-hydroxyalkanoate + NADP+ = an (R)-2-alkyl-3-oxoalkanoate + NADPH + H+
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
MetaCyc
cis-alkene biosynthesis, hentriaconta-3,6,9,12,15,19,22,25,28-nonaene biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
(2R,3S)-2-alkyl-3-hydroxyalkanoate:NADP+ oxidoreductase
The enzyme, found in certain bacterial species, is part of a pathway for the production of olefins.
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
syn-2-decyl-3-hydroxytetradecanoic acid + NADPH + H+
?
Substrates: 100% activity
Products: -
Products: -
?
syn-2-octyl-3-hydroxydodecanoic acid + NADPH + H+
?
Substrates: 20% activity compared to syn-2-decyl-3-hydroxytetradecanoic acid
Products: -
Products: -
?
(2R,3S)-2-alkyl-3-hydroxyalkanoate + NADP+
(R)-2-alkyl-3-oxoalkanoate + NADPH + H+
Substrates: -
Products: -
Products: -
r
(2R,3S)-2-alkyl-3-hydroxyalkanoate + NADP+
(R)-2-alkyl-3-oxoalkanoate + NADPH + H+
Substrates: -
Products: -
Products: -
r
(2R,3S)-2-hexyl-3-hydroxydecanoic acid + NADPH + H+
?
Substrates: -
Products: -
Products: -
?
(2R,3S)-2-hexyl-3-hydroxydecanoic acid + NADPH + H+
?
Substrates: -
Products: -
Products: -
?
(2R/2S)-2-hexyl-3-oxodecanoic acid + NADPH + H+
?
Substrates: 13% activity compared to syn-2-decyl-3-hydroxytetradecanoic acid
Products: -
Products: -
?
(2R/2S)-2-hexyl-3-oxodecanoic acid + NADPH + H+
?
Substrates: 13% activity compared to syn-2-decyl-3-hydroxytetradecanoic acid
Products: -
Products: -
?
(R)-2-alkyl-3-oxoalkanoate + NADPH + H+
(2R,3S)-2-alkyl-3-hydroxyalkanoate + NADP+
Substrates: -
Products: -
Products: -
r
(R)-2-alkyl-3-oxoalkanoate + NADPH + H+
(2R,3S)-2-alkyl-3-hydroxyalkanoate + NADP+
-
Substrates: -
Products: -
Products: -
r
(R)-2-alkyl-3-oxoalkanoate + NADPH + H+
(2R,3S)-2-alkyl-3-hydroxyalkanoate + NADP+
Substrates: -
Products: -
Products: -
r
syn-2-hexyl-3-hydroxydecanoic acid + NADPH + H+
?
Substrates: 15% activity compared to syn-2-decyl-3-hydroxytetradecanoic acid
Products: -
Products: -
?
syn-2-hexyl-3-hydroxydecanoic acid + NADPH + H+
?
Substrates: 15% activity compared to syn-2-decyl-3-hydroxytetradecanoic acid
Products: -
Products: -
?
additional information
?
-
Substrates: no activity with syn-2-butyl-3-hydroxyoctanoic acid, 3-oxodecanoic acid, and 3-hydroxydecanoic acid
Products: -
Products: -
?
additional information
?
-
-
Substrates: no activity with syn-2-butyl-3-hydroxyoctanoic acid, 3-oxodecanoic acid, and 3-hydroxydecanoic acid
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2R,3S)-2-alkyl-3-hydroxyalkanoate + NADP+
(R)-2-alkyl-3-oxoalkanoate + NADPH + H+
Substrates: -
Products: -
Products: -
r
(2R,3S)-2-alkyl-3-hydroxyalkanoate + NADP+
(R)-2-alkyl-3-oxoalkanoate + NADPH + H+
Substrates: -
Products: -
Products: -
r
(R)-2-alkyl-3-oxoalkanoate + NADPH + H+
(2R,3S)-2-alkyl-3-hydroxyalkanoate + NADP+
Substrates: -
Products: -
Products: -
r
(R)-2-alkyl-3-oxoalkanoate + NADPH + H+
(2R,3S)-2-alkyl-3-hydroxyalkanoate + NADP+
-
Substrates: -
Products: -
Products: -
r
(R)-2-alkyl-3-oxoalkanoate + NADPH + H+
(2R,3S)-2-alkyl-3-hydroxyalkanoate + NADP+
Substrates: -
Products: -
Products: -
r
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.181
(2R,3S)-2-hexyl-3-hydroxydecanoic acid
at pH 8.0 and 25°C
0.161
(2R/2S)-2-hexyl-3-oxodecanoic acid
at pH 8.0 and 25°C
0.031
syn-2-decyl-3-hydroxytetradecanoic acid
at pH 8.0 and 25°C
0.202
syn-2-hexyl-3-hydroxydecanoic acid
at pH 8.0 and 25°C
0.214
syn-2-octyl-3-hydroxydodecanoic acid
at pH 8.0 and 25°C
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1.3
(2R,3S)-2-hexyl-3-hydroxydecanoic acid
at pH 8.0 and 25°C
0.97
(2R/2S)-2-hexyl-3-oxodecanoic acid
at pH 8.0 and 25°C
1.4
syn-2-decyl-3-hydroxytetradecanoic acid
at pH 8.0 and 25°C
1.2
syn-2-hexyl-3-hydroxydecanoic acid
at pH 8.0 and 25°C
2
syn-2-octyl-3-hydroxydodecanoic acid
at pH 8.0 and 25°C
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
7.3
(2R,3S)-2-hexyl-3-hydroxydecanoic acid
at pH 8.0 and 25°C
47.9
syn-2-decyl-3-hydroxytetradecanoic acid
at pH 8.0 and 25°C
9.6
syn-2-octyl-3-hydroxydodecanoic acid
at pH 8.0 and 25°C
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). OLED_STRMK
Stenotrophomonas maltophilia (strain K279a)
330
0
35480
Swiss-Prot
-
OLED_SHEON
Shewanella oneidensis (strain ATCC 700550 / JCM 31522 / CIP 106686 / LMG 19005 / NCIMB 14063 / MR-1)
387
0
41885
Swiss-Prot
-
OLED_XANCP
Xanthomonas campestris pv. campestris (strain ATCC 33913 / DSM 3586 / NCPPB 528 / LMG 568 / P 25)
337
0
36252
Swiss-Prot
-
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
77124
His6-tagged enzyme, calculated from amino acid sequence
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
homodimer
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Bonnett, S.A.; Papireddy, K.; Higgins, S.; del Cardayre, S.; Reynolds, K.A.
Functional characterization of an NADPH dependent 2-alkyl-3-ketoalkanoic acid reductase involved in olefin biosynthesis in Stenotrophomonas maltophilia
Biochemistry
50
9633-9640
2011
Stenotrophomonas maltophilia (B2FI29), Stenotrophomonas maltophilia, Stenotrophomonas maltophilia K279a (B2FI29)
brenda
Kancharla, P.; Bonnett, S.A.; Reynolds, K.A.
Stenotrophomonas maltophilia OleC-catalyzed ATP-dependent formation of long-chain Z-olefins from 2-alkyl-3-hydroxyalkanoic acids
ChemBioChem
17
1426-1429
2016
Stenotrophomonas maltophilia (B2FI29), Stenotrophomonas maltophilia K279a (B2FI29)
brenda
EXTERNAL LINKS (specific for EC-Number 1.1.1.412)
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