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Enzyme Nomenclature
Information on EC 1.14.19.29 - sphingolipid 8-(E/Z)-desaturase
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
1.14.19.29
-
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RECOMMENDED NAME
GeneOntology No.
sphingolipid 8-(E/Z)-desaturase
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a (4R)-4-hydroxysphinganine ceramide + 2 ferrocytochrome b5 + O2 + 2 H+ = a (4R,8E)-4-hydroxysphing-8-enine ceramide + 2 ferricytochrome b5 + 2 H2O
a (4R)-4-hydroxysphinganine ceramide + 2 ferrocytochrome b5 + O2 + 2 H+ = a (4R,8Z)-4-hydroxysphing-8-enine ceramide + 2 ferricytochrome b5 + 2 H2O
a (4R)-4-hydroxysphinganine ceramide + 2 ferrocytochrome b5 + O2 + 2 H+ = a (4R,8E)-4-hydroxysphing-8-enine ceramide + 2 ferricytochrome b5 + 2 H2O
(1)
-
-
-
a (4R)-4-hydroxysphinganine ceramide + 2 ferrocytochrome b5 + O2 + 2 H+ = a (4R,8E)-4-hydroxysphing-8-enine ceramide + 2 ferricytochrome b5 + 2 H2O
(1)
-
a (4R)-4-hydroxysphinganine ceramide + 2 ferrocytochrome b5 + O2 + 2 H+ = a (4R,8Z)-4-hydroxysphing-8-enine ceramide + 2 ferricytochrome b5 + 2 H2O
(2)
-
-
-
a (4R)-4-hydroxysphinganine ceramide + 2 ferrocytochrome b5 + O2 + 2 H+ = a (4R,8Z)-4-hydroxysphing-8-enine ceramide + 2 ferricytochrome b5 + 2 H2O
(2)
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
(4R)-4-hydroxysphinganine ceramide,ferrocytochrome b5:oxygen oxidoreductase (8,9 cis/trans-dehydrogenating)
The enzymes from higher plants convert sphinganine, 4E-sphing-4-enine and phytosphinganine into E/Z-mixtures of Delta8-desaturated products displaying different proportions of geometrical isomers depending on plant species. The nature of the actual desaturase substrate has not yet been studied experimentally. The enzymes contain an N-terminal cytochrome b5 domain that acts as the direct electron donor to the active site of the desaturase [1]. The homologous enzymes from some yeasts and diatoms, EC 1.14.19.18, sphingolipid 8-(E)-desaturase, act on sphing-4-enine ceramides and produce only the trans isomer.
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
physiological function
malfunction
-
gene disruption leads to a decreased hyphal growth rate and increased sensitivity against SDS compared with the wild type strain
malfunction
-
enzyme deletion mutants reveal a 50% reduction in glucosylceramide levels and a corresponding increase in glycosylinositolphosphoceramides
malfunction
-
gene disruption leads to a decreased hyphal growth rate and increased sensitivity against SDS compared with the wild type strain
-
physiological function
DELTA8 sphingobase desaturase confer aluminum tolerance in seedlings
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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
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8E)-4-hydroxysphing-8-enine ceramide + (4R,8Z)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8E)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8Z)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
(E)-sphing-4-enine + ferrocytochrome b5 + O2 + H+
(4E,8E)-sphinga-4,8-dienine + ferricytochrome b5 + H2O
C18-phytosphinganine + ferrocytochrome b5 + O2 + H+
C18-8-phytosphingenine + ferricytochrome b5 + H2O
-
-
-
?
C18-phytosphinganine + ferrocytochrome b5 + O2 + H+
DELTA8-trans/cis-C18-phytosphingenine + ferricytochrome b5 + H2O
C20-phytosphinganine + ferrocytochrome b5 + O2 + H+
DELTA8-trans/cis-C-20-phytosphingenine + ferricytochrome b5 + H2O
-
-
-
?
C20-phytosphinganine + ferrocytochrome b5 + O2 + H+
DELTA8-trans/cis-C20-phytosphingenine + ferricytochrome b5 + H2O
fluorinated phytosphinganine + ferrocytochrome b5 + O2 + H+
?
-
the presence of a fluorine atom at the position of the initial hydrogen removal C8-HR leads to a complete suppression of the desaturation reaction, while replacement of C8-HS with fluorine generates a mixture of mainly (Z)- and trace amounts of (E)-fluoroolefine
-
-
?
phytosphinganine + 2 ferrocytochrome b5 + O2 + 2 H+
(4R,8E)-4-hydroxy-8-sphingenine + 2 ferricytochrome b5 + 2 H2O
phytosphinganine + 2 ferrocytochrome b5 + O2 + 2 H+
(4R,8Z)-4-hydroxy-8-sphingenine + 2 ferricytochrome b5 + 2 H2O
sphinganine + ferrocytochrome b5 + O2 + H+
8-sphingenine + ferricytochrome b5 + H2O
-
-
-
?
sphinganine ceramide + ferrocytochrome b5 + O2 + H+
8-sphingenine ceramide + ferricytochrome b5 + H2O
-
-
-
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8E)-4-hydroxysphing-8-enine ceramide + (4R,8Z)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
-
the ratio of trans:cis products is approximately 4:1 for isoform SLD1 and 7:1 for isoform SLD2
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8E)-4-hydroxysphing-8-enine ceramide + (4R,8Z)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
-
7:1 product mixture of (4R,8E)- and (4R,8Z)-4-hydroxy-sphing-8-enine ceramide
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8E)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
39.8% conversion rate
-
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8E)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
-
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8E)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
-
-
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8E)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
-
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8E)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
-
-
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8E)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
32.5% conversion rate
-
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8E)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
-
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8Z)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
7.5% conversion rate
-
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8Z)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
-
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8Z)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
-
-
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8Z)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
-
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8Z)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
-
-
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8Z)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
32.5% conversion rate
-
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8Z)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
the enzyme exhibits preference for (Z)-isomer formation
-
?
(E)-sphing-4-enine + ferrocytochrome b5 + O2 + H+
(4E,8E)-sphinga-4,8-dienine + ferricytochrome b5 + H2O
-
-
-
-
?
(E)-sphing-4-enine + ferrocytochrome b5 + O2 + H+
(4E,8E)-sphinga-4,8-dienine + ferricytochrome b5 + H2O
-
-
-
-
?
C18-phytosphinganine + ferrocytochrome b5 + O2 + H+
DELTA8-trans/cis-C18-phytosphingenine + ferricytochrome b5 + H2O
-
-
-
-
?
C18-phytosphinganine + ferrocytochrome b5 + O2 + H+
DELTA8-trans/cis-C18-phytosphingenine + ferricytochrome b5 + H2O
-
-
-
-
?
C18-phytosphinganine + ferrocytochrome b5 + O2 + H+
DELTA8-trans/cis-C18-phytosphingenine + ferricytochrome b5 + H2O
-
-
-
?
C20-phytosphinganine + ferrocytochrome b5 + O2 + H+
DELTA8-trans/cis-C20-phytosphingenine + ferricytochrome b5 + H2O
-
-
-
-
?
C20-phytosphinganine + ferrocytochrome b5 + O2 + H+
DELTA8-trans/cis-C20-phytosphingenine + ferricytochrome b5 + H2O
-
-
-
-
?
phytosphinganine + 2 ferrocytochrome b5 + O2 + 2 H+
(4R,8E)-4-hydroxy-8-sphingenine + 2 ferricytochrome b5 + 2 H2O
-
-
-
-
?
phytosphinganine + 2 ferrocytochrome b5 + O2 + 2 H+
(4R,8E)-4-hydroxy-8-sphingenine + 2 ferricytochrome b5 + 2 H2O
-
the enzyme expressed in Saccharomyces cerevisiae converts 4-hydroxy-sphinganine (phytosphinganine) into a 7:1 mixture of (4R,8E)- and (4R,8Z)-4-hydroxy-8-sphingenine. Both desaturation steps leading to either the 8E or the 8Z isomer of 4-hydroxy-8-sphingenine involved the syn elimination of two vicinal hydrogen atoms
-
-
?
phytosphinganine + 2 ferrocytochrome b5 + O2 + 2 H+
(4R,8Z)-4-hydroxy-8-sphingenine + 2 ferricytochrome b5 + 2 H2O
-
-
(2)
-
?
phytosphinganine + 2 ferrocytochrome b5 + O2 + 2 H+
(4R,8Z)-4-hydroxy-8-sphingenine + 2 ferricytochrome b5 + 2 H2O
-
the enzyme expressed in Saccharomyces cerevisiae converts 4-hydroxy-sphinganine (phytosphinganine) into a 7:1 mixture of (4R,8E)- and (4R,8Z)-4-hydroxy-8-sphingenine. Both desaturation steps leading to either the 8E or the 8Z isomer of 4-hydroxy-8-sphingenine involved the syn elimination of two vicinal hydrogen atoms
(2)
-
?
additional information
?
-
-
no activity with palmitoleic acid, linoleic acid, and alpha-linolenic acid
-
-
-
additional information
?
-
the enzyme lacks DELTA6-desaturase activity
-
-
-
additional information
?
-
-
the enzyme lacks DELTA6-desaturase activity
-
-
-
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NATURAL SUBSTRATES
NATURAL PRODUCTS
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
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8E)-4-hydroxysphing-8-enine ceramide + (4R,8Z)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8E)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8Z)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
(E)-sphing-4-enine + ferrocytochrome b5 + O2 + H+
(4E,8E)-sphinga-4,8-dienine + ferricytochrome b5 + H2O
C18-phytosphinganine + ferrocytochrome b5 + O2 + H+
C18-8-phytosphingenine + ferricytochrome b5 + H2O
Q9FR82
-
-
-
?
C18-phytosphinganine + ferrocytochrome b5 + O2 + H+
DELTA8-trans/cis-C18-phytosphingenine + ferricytochrome b5 + H2O
C20-phytosphinganine + ferrocytochrome b5 + O2 + H+
DELTA8-trans/cis-C-20-phytosphingenine + ferricytochrome b5 + H2O
Q43469
-
-
-
?
C20-phytosphinganine + ferrocytochrome b5 + O2 + H+
DELTA8-trans/cis-C20-phytosphingenine + ferricytochrome b5 + H2O
phytosphinganine + 2 ferrocytochrome b5 + O2 + 2 H+
(4R,8E)-4-hydroxy-8-sphingenine + 2 ferricytochrome b5 + 2 H2O
-
-
-
-
?
phytosphinganine + 2 ferrocytochrome b5 + O2 + 2 H+
(4R,8Z)-4-hydroxy-8-sphingenine + 2 ferricytochrome b5 + 2 H2O
-
-
(2)
-
?
sphinganine + ferrocytochrome b5 + O2 + H+
8-sphingenine + ferricytochrome b5 + H2O
Q9FR82
-
-
-
?
sphinganine ceramide + ferrocytochrome b5 + O2 + H+
8-sphingenine ceramide + ferricytochrome b5 + H2O
-
-
-
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8E)-4-hydroxysphing-8-enine ceramide + (4R,8Z)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
-
the ratio of trans:cis products is approximately 4:1 for isoform SLD1 and 7:1 for isoform SLD2
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8E)-4-hydroxysphing-8-enine ceramide + (4R,8Z)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
-
7:1 product mixture of (4R,8E)- and (4R,8Z)-4-hydroxy-sphing-8-enine ceramide
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8E)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
39.8% conversion rate
-
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8E)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
G9I7G1
-
-
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8E)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
-
-
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8E)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
A4GK73
-
-
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8E)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
-
-
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8E)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
32.5% conversion rate
-
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8E)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
A7Y7E1
-
-
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8Z)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
7.5% conversion rate
-
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8Z)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
G9I7G1
-
-
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8Z)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
-
-
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8Z)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
A4GK73
-
-
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8Z)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
-
-
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8Z)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
32.5% conversion rate
-
-
?
(4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
(4R,8Z)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
A7Y7E1
-
the enzyme exhibits preference for (Z)-isomer formation
-
?
(E)-sphing-4-enine + ferrocytochrome b5 + O2 + H+
(4E,8E)-sphinga-4,8-dienine + ferricytochrome b5 + H2O
-
-
-
-
?
(E)-sphing-4-enine + ferrocytochrome b5 + O2 + H+
(4E,8E)-sphinga-4,8-dienine + ferricytochrome b5 + H2O
-
-
-
-
?
C18-phytosphinganine + ferrocytochrome b5 + O2 + H+
DELTA8-trans/cis-C18-phytosphingenine + ferricytochrome b5 + H2O
-
-
-
-
?
C18-phytosphinganine + ferrocytochrome b5 + O2 + H+
DELTA8-trans/cis-C18-phytosphingenine + ferricytochrome b5 + H2O
-
-
-
-
?
C18-phytosphinganine + ferrocytochrome b5 + O2 + H+
DELTA8-trans/cis-C18-phytosphingenine + ferricytochrome b5 + H2O
Q43469
-
-
-
?
C20-phytosphinganine + ferrocytochrome b5 + O2 + H+
DELTA8-trans/cis-C20-phytosphingenine + ferricytochrome b5 + H2O
-
-
-
-
?
C20-phytosphinganine + ferrocytochrome b5 + O2 + H+
DELTA8-trans/cis-C20-phytosphingenine + ferricytochrome b5 + H2O
-
-
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
-
primarily expressed in young leaves; primarily expressed in young leaves
additional information
no detectable expression is observed in roots, mature leaves, small flower buds nor in fully developed flowers at anthesis
additional information
-
no detectable expression is observed in roots, mature leaves, small flower buds nor in fully developed flowers at anthesis
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed as chimera protein with DELTA6 fatty acid desaturase in Saccharomyces cervisiae
-
expressed in Saccharomyces cerevisiae
expressed in Saccharomyces cerevisiae strain INVScl mutant sur2DELTA lacking sphinganine C4-hydroxylase
expressed in Saccharomyces cerevisiae strain w303-1a; expression of this openreading frame in Saccharomyces cerevisiae results in the formation of DELTA8-trans/cis-phytosphingenines not present in wild-type cells
-
expressed in Saccharomyces cerevisiae; the open reading frame is cloned behind the constitutive ADH1 promotor of the yeast expression vector pVT-U-102 and transformed in Saccharomyces cerevisiae INVSc1
-
expressed in Saccharomyces cerevisiae strain INVScl mutant sur2DELTA lacking sphinganine C4-hydroxylase
-
expressed in Saccharomyces cerevisiae strain INVScl mutant sur2DELTA lacking sphinganine C4-hydroxylase
-
expressed in Saccharomyces cerevisiae strain INVScl mutant sur2DELTA lacking sphinganine C4-hydroxylase
-
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
F59R
the mutant shows severely reduced activity compared to the wild type enzyme
L369A
the mutant shows severely reduced activity compared to the wild type enzyme
Q372H
the mutant shows severely reduced activity compared to the wild type enzyme
W190A
the mutant shows severely reduced activity compared to the wild type enzyme
W345A
the mutant shows severely reduced activity compared to the wild type enzyme
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.19.29)
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