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(2S,3R)-2-aminoicosane-1,3-diol + reduced acceptor + O2
(E)-(2S,3R)-2-aminoicos-8-ene-1,3-diol + (Z)-(2S,3R)-2-aminoicos-8-ene-1,3-diol + acceptor + H2O
-
-
-
-
?
(E)-sphing-4-enine + reduced acceptor + O2
(2S,3R,4E,8E)-2-aminooctadeca-4,8-diene-1,3-diol + acceptor + H2O
(R)-9-fluorophytosphinganine + reduced acceptor + O2
(Z)-9-fluoro-8-phytosphingenine + acceptor + H2O
-
exclusively produces (Z)-9-fluoro-8-phytosphingenine. This result is explained by an initial attack onto the C8-HR and syn-elimination of two vicinal hydrogen atoms via an anti-conformation of the substrate. An initial attack on the C9-F is excluded and generates no product
-
-
?
(S)-8-fluorophytosphinganine + reduced acceptor + O2
(Z)-8-fluoro-8-phytosphingenine + acceptor + H2O
-
product predominantly transformed to (Z)-8-fluoro-8-phytosphingenine along with only trace amounts of the (E)-8-fluoro-8-phytosphingenine (ratio 95:5). This ratio indicates that the fluorinated substrate strongly favors the anti-configuration at the active center of the desaturase
-
-
?
(S)-9-fluorophytosphinganine + reduced acceptor + O2
(E)-9-fluoro-8-phytosphingenine + acceptor + H2O
-
produces (E)-9-fluoro-8-phytosphingenine as the sole reaction product. Only the initial attack on the C9-HR in combination with the gauche-conformation of the substrate is productive
-
-
?
11,14,17-eicosatrienoic acid + reduced acceptor + O2
8,11,14,17-eicosatetraenoic acid + acceptor + H2O
-
-
-
?
11,14,17-eicosatrienoic acid + reduced acceptor + O2
?
20:3n-3, yield 20:4n-3
-
-
?
11,14-eicosadienoic acid + reduced acceptor + O2
8,11,14-eicosatrienoic acid + acceptor + H2O
-
-
-
?
11,14-eicosadienoic acid + reduced acceptor + O2
?
20:2n-6, yield 20:3n-6
-
-
?
11-eicosenoic acid + reduced acceptor + O2
8,11-eicosadienoic acid + acceptor + H2O
-
-
-
?
4-hydroxysphinganine + reduced acceptor + H2O
4-hydroxy-trans-8-sphingenine + acceptor + H2O
DELTA4-sphingenine + reduced acceptor + O2
DELTA4,8-sphingadienine + acceptor + 2 H2O
-
production of two water molecules in the reaction
-
?
phytosphinganine + reduced acceptor + O2
(8E)-4-hydroxy-8-sphingenine + (8Z)-4-hydroxy-8-sphingenine + acceptor + H2O
-
reaction in a in a stereospecific manner by syn elimination of two vicinal hydrogen atoms
production of two water molecules in the reaction
-
?
phytosphinganine + reduced acceptor + O2
DELTA8-phytosphingenine + acceptor + H2O
-
production of two water molecules in the reaction
-
?
phytosphinganine + reduced acceptor + O2
trans-8-sphingenine + cis-8-sphingenine + acceptor + H2O
sphinganine + reduced acceptor + O2
DELTA8-sphingenine + acceptor + 2 H2O
-
production of two water molecules in the reaction
-
?
additional information
?
-
(E)-sphing-4-enine + reduced acceptor + O2
(2S,3R,4E,8E)-2-aminooctadeca-4,8-diene-1,3-diol + acceptor + H2O
-
-
-
-
?
(E)-sphing-4-enine + reduced acceptor + O2
(2S,3R,4E,8E)-2-aminooctadeca-4,8-diene-1,3-diol + acceptor + H2O
-
-
-
-
?
4-hydroxysphinganine + reduced acceptor + H2O
4-hydroxy-trans-8-sphingenine + acceptor + H2O
-
-
-
?
4-hydroxysphinganine + reduced acceptor + H2O
4-hydroxy-trans-8-sphingenine + acceptor + H2O
-
-
-
-
?
phytosphinganine + reduced acceptor + O2
trans-8-sphingenine + cis-8-sphingenine + acceptor + H2O
-
-
-
?
phytosphinganine + reduced acceptor + O2
trans-8-sphingenine + cis-8-sphingenine + acceptor + H2O
-
-
-
-
?
additional information
?
-
desaturation of long-chain base moieties of sphingolipid classes (ceramide, hydroxyceramide, GlcCer, and GIPC) during cold treatment, overview
-
-
?
additional information
?
-
desaturation of long-chain base moieties of sphingolipid classes (ceramide, hydroxyceramide, GlcCer, and GIPC) during cold treatment, overview
-
-
?
additional information
?
-
desaturation of long-chain base moieties of sphingolipid classes (ceramide, hydroxyceramide, GlcCer, and GIPC) during cold treatment, overview
-
-
?
additional information
?
-
desaturation of long-chain base moieties of sphingolipid classes (ceramide, hydroxyceramide, GlcCer, and GIPC) during cold treatment, overview
-
-
?
additional information
?
-
-
(R)-8-fluorophytosphinganine does not yield any desaturation product
-
-
?
additional information
?
-
DELTA8 sphingolipid desaturase creates double bonds in long-chain bases, i.e. sphingobases, such as sphinganine, phytosphinganine, or 4-sphingenine to produce E- and Z-isomers of 8-sphingenine, 8-phytosphingenine, or 4,8-sphingadienine, respectively
-
-
?
additional information
?
-
-
DELTA8 sphingolipid desaturase creates double bonds in long-chain bases, i.e. sphingobases, such as sphinganine, phytosphinganine, or 4-sphingenine to produce E- and Z-isomers of 8-sphingenine, 8-phytosphingenine, or 4,8-sphingadienine, respectively
-
-
?
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DELTA4-sphingenine + reduced acceptor + O2
DELTA4,8-sphingadienine + acceptor + 2 H2O
-
production of two water molecules in the reaction
-
?
phytosphinganine + reduced acceptor + O2
DELTA8-phytosphingenine + acceptor + H2O
-
production of two water molecules in the reaction
-
?
sphinganine + reduced acceptor + O2
DELTA8-sphingenine + acceptor + 2 H2O
-
production of two water molecules in the reaction
-
?
additional information
?
-
additional information
?
-
desaturation of long-chain base moieties of sphingolipid classes (ceramide, hydroxyceramide, GlcCer, and GIPC) during cold treatment, overview
-
-
?
additional information
?
-
desaturation of long-chain base moieties of sphingolipid classes (ceramide, hydroxyceramide, GlcCer, and GIPC) during cold treatment, overview
-
-
?
additional information
?
-
desaturation of long-chain base moieties of sphingolipid classes (ceramide, hydroxyceramide, GlcCer, and GIPC) during cold treatment, overview
-
-
?
additional information
?
-
desaturation of long-chain base moieties of sphingolipid classes (ceramide, hydroxyceramide, GlcCer, and GIPC) during cold treatment, overview
-
-
?
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brenda
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brenda
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brenda
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brenda
additional information
expression of isozyme AtSLD2 is limited to flowers and siliques. AtSLD1 contributes to DELTA8 LCB desaturation in stems, flowers, leaves, siliques and roots, while isozyme AtSLD2 has a small effect on desaturation in every tissue, even in flowers and siliques, where AtSLD2 is highly expressed
brenda
additional information
expression of isozyme AtSLD2 is limited to flowers and siliques. AtSLD1 contributes to DELTA8 LCB desaturation in stems, flowers, leaves, siliques and roots, while isozyme AtSLD2 has a small effect on desaturation in every tissue, even in flowers and siliques, where AtSLD2 is highly expressed
brenda
additional information
isozyme AtSLD1 is broadly expressed in all tissues. AtSLD1 contributes to DELTA8 LCB desaturation in stems, flowers, leaves, siliques and roots, while isozyme AtSLD2 has a small effect on desaturation in every tissue, even in flowers and siliques, where AtSLD2 is highly expressed
brenda
additional information
isozyme AtSLD1 is broadly expressed in all tissues. AtSLD1 contributes to DELTA8 LCB desaturation in stems, flowers, leaves, siliques and roots, while isozyme AtSLD2 has a small effect on desaturation in every tissue, even in flowers and siliques, where AtSLD2 is highly expressed
brenda
additional information
-
expression of isozyme AtSLD2 is limited to flowers and siliques. AtSLD1 contributes to DELTA8 LCB desaturation in stems, flowers, leaves, siliques and roots, while isozyme AtSLD2 has a small effect on desaturation in every tissue, even in flowers and siliques, where AtSLD2 is highly expressed
-
brenda
additional information
-
isozyme AtSLD1 is broadly expressed in all tissues. AtSLD1 contributes to DELTA8 LCB desaturation in stems, flowers, leaves, siliques and roots, while isozyme AtSLD2 has a small effect on desaturation in every tissue, even in flowers and siliques, where AtSLD2 is highly expressed
-
brenda
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A44G
-
expressed in yeast, 2-fold higher activity toward 20:2 (n-6), but nor alternation in activity towards 20:3 (n-3) in comparison with the wild-type
F59R
-
the mutant shows markedly decreased activity compared to the wild type enzyme
G28R
-
the mutant shows decreased activity compared to the wild type enzyme
G52R
-
the mutant shows wild type activity
L369A
-
the mutant shows markedly decreased activity compared to the wild type enzyme
L71R
-
the mutant shows wild type activity
Q372H
-
the mutant shows markedly decreased activity compared to the wild type enzyme
T56R
-
the mutant shows decreased activity compared to the wild type enzyme
W190A
-
the mutant shows markedly decreased activity compared to the wild type enzyme
W345A
-
the mutant shows markedly decreased activity compared to the wild type enzyme
Y31A
-
the mutant shows decreased activity compared to the wild type enzyme
additional information
generation of isozymes SLD1 and SLD2 knockout mutant, sphingolipid content in sld1sld2 and Bax inhibitor-1 atbi-1 mutant during cold treatment, overview
additional information
generation of isozymes SLD1 and SLD2 knockout mutant, sphingolipid content in sld1sld2 and Bax inhibitor-1 atbi-1 mutant during cold treatment, overview
additional information
-
generation of isozymes SLD1 and SLD2 knockout mutant, sphingolipid content in sld1sld2 and Bax inhibitor-1 atbi-1 mutant during cold treatment, overview
-
additional information
chimeras of DELTA6-fatty acid and DELTA8-sphingolipid desaturases
additional information
-
chimeras of DELTA6-fatty acid and DELTA8-sphingolipid desaturases
additional information
-
a virus-induced gene silencing (VIGS) approach to knockdown gene SlSLD expression is used in tomato leaves involving transformation via Agrobacterium GV3101, chilling resistance is evaluated for wild-type and mutangt plant seedlings, determination of the mutant phenotype, detailed overview. After exposure to 4°C, SlSLD-silenced mutant tomato plants are severely damaged. Exposure to low temperature severely damages chloroplasts in SlSLD-silenced plants
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cloned into pBINI19-35S, transferred to Agrobacterium tumefaciens strain GV3101 and expressed in wild-type Arabidopsis Col 0 or in transgenic line CA1-9 expressing the Isochrysis galbana elongating activity IgASE1
-
cloned into the yeast expression vector pYES2 and expressed in Saccharomyces serevisiae strain W303-1A
-
expressed in yeast cells
-
expression in Saccharomyces cerevisiae
expression in Saccharomyces cerevisiae confers tolerance to aluminium to the cells
AF001394
expression of this open-reading frame in Saccharomyces cerevisiae results in the formation of DELTA-trans/cis-phytosphingenines not present in wild-type cells
functional expression in Saccharomyces cerevisiae, using the constitutive ADH1 promotor of the yeast expression vector pVT-U-102, results in synthesis of acylated (8E)- and (8Z)-4-hydroxy-8-sphingenine via N-acyl-4-hydroxysphinganine from fed deuterium-labeled palmitic acid, primary kinetic isotope effects, overview
-
gene AtSLD1, sequence comparisons, quantitative enzyme expression analysis, recombinant expression as cYFP fusion protein driven by cauliflower mosaic virus 35S (CaMV35S) promoter in onion epidermal cells, coexpression of AtBI-1-cYFP and AtSLD1-nYFP
gene AtSLD2, sequence comparions, quantitative enzyme expression analysis, recombinant expression as cYFP fusion protein driven by cauliflower mosaic virus 35S (CaMV35S) promoter in onion epidermal cells
gene S581, DNA and amino acid sequence determination and analysis, expression in Saccharomyces cerevisiae and constitutively in Arabidopsis thaliana, under control of the CaMV35S promoter, confers tolerance to aluminium and gadolinium, Gd3+, but not to lanthanum, La3+, or manganese, Mn2+, to cells and seedlings, respectively, the transgenic expression leads to the accumulation of 8(Z/E)-C18-phytosphingenine and 8(Z/E)-C20-phytopshingenine in yeast and to the accumulation of 8(Z/E)-C18-phytosphingenine in the leaves and roots of Arabidopsis plants, overview
genes SlSLD1 and SlSLD2, quantitative RT-PCR enzyme expression analysis
-
into pBluescript II SK+ and subsequently into pFLAG-Act1
-
into the pGEM-T easy vector for sequencing, into the pYES2 vector for expression in Saccharomyces cerevisiae cells
expression in Saccharomyces cerevisiae
-
expression in Saccharomyces cerevisiae
-
expression in Saccharomyces cerevisiae
expression in Saccharomyces cerevisiae
expression in Saccharomyces cerevisiae
expression in Saccharomyces cerevisiae
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Wallis, J.G.; Browse, J.
The DELTA8-desaturase of Euglena gracilis: an alternate pathway for synthesis of 20-carbon polyunsaturated fatty acids
Arch. Biochem. Biophys.
365
307-316
1999
Euglena gracilis (Q9SWQ9), Euglena gracilis
brenda
Sperling, P.; Libisch, B.; Zahringer, U.; Napier, J.A.; Heinz, E.
Functional identification of a DELTA8-sphingolipid desaturase from Borago officinalis
Arch. Biochem. Biophys.
388
293-298
2001
Borago officinalis (Q9FR82), Borago officinalis
brenda
Libisch, B.; Michaelson, L.V.; Lewis, M.J.; Shewry, P.R.; Napier, J.A.
Chimeras of DELTA6-fatty acid and DELTA8-sphingolipid desaturases
Biochem. Biophys. Res. Commun.
279
779-785
2000
Borago officinalis (Q9FR82), Borago officinalis
brenda
Sperling, P.; Blume, A.; Zahringer, U.; Heinz, E.
Further characterization of DELTA8-sphingolipid desaturases from higher plants
Biochem. Soc. Trans.
28
638-641
2000
Helianthus annuus
brenda
Michaelson, L.V.; Longman, A.J.; Sayanova, O.; Stobart, A.K.; Napier, J.A.
Isolation and characterization of a cDNA encoding a DELTA8 sphingolipid desaturase from Aquilegia vulgaris
Biochem. Soc. Trans.
30
1073-1075
2002
Aquilegia vulgaris (Q8LLD7), Aquilegia vulgaris
brenda
Takakuwa, N.; Kinoshita, M.; Oda, Y.; Ohnishi, M.
Isolation and characterization of the genes encoding DELTA8-sphingolipid desaturase from Saccharomyces kluyveri and Kluyveromyces lactis
Curr. Microbiol.
45
459-461
2002
Kluyveromyces lactis (Q8NKG8), Lachancea kluyveri (Q8NKG9)
brenda
Tonon, T.; Sayanova, O.; Michaelson, L.V.; Qing, R.; Harvey, D.; Larson, T.R.; Li, Y.; Napier, J.A.; Graham, I.A.
Fatty acid desaturases from the microalga Thalassiosira pseudonana
FEBS J.
272
3401-3412
2005
Thalassiosira pseudonana
brenda
Chen, Q.; Yin, F.Q.; Sprecher, H.
The questionable role of a microsomal DELTA8 acyl-CoA-dependent desaturase in the biosynthesis of polyunsaturated fatty acids
Lipids
35
871-879
2000
Rattus norvegicus
brenda
Tripodi, K.E.; Buttigliero, L.V.; Altabe, S.G.; Uttaro, A.D.
Functional characterization of front-end desaturases from trypanosomatids depicts the first polyunsaturated fatty acid biosynthetic pathway from a parasitic protozoan
FEBS J.
273
271-280
2006
Leishmania major
brenda
Sayanova, O.; Haslam, R.; Qi, B.; Lazarus, C.M.; Napier, J.A.
The alternative pathway C20 DELTA8-desaturase from the non-photosynthetic organism Acanthamoeba castellanii is an atypical cytochrome b5-fusion desaturase
FEBS Lett.
580
1946-1952
2006
Acanthamoeba castellanii
brenda
Beckmann Christop, B.C.; Rattke Janin, R.J.; Oldham Neil, O.N.; Sperling Petr, S.P.; Heinz Erns, H.E.; Boland Wilhel, B.W.
Characterization of a DELTA8-sphingolipid desaturase from higher plants: a stereochemical and mechanistic study on the origin of E,Z isomers
Angew. Chem. Int. Ed. Engl.
41
2298-2300
2002
Helianthus annuus, no activity in Saccharomyces cerevisiae
brenda
Ryan, P.R.; Liu, Q.; Sperling, P.; Dong, B.; Franke, S.; Delhaize, E.
A higher plant DELTA8 sphingolipid desaturase with a preference for (Z)-isomer formation confers aluminum tolerance to yeast and plants
Plant Physiol.
144
1968-1977
2007
Stylosanthes hamata (A7Y7E1), Stylosanthes hamata, Arabidopsis thaliana (AF001394)
brenda
Park, W.J.; Kothapalli, K.S.; Lawrence, P.; Tyburczy, C.; Brenna, J.T.
An alternate pathway to long-chain polyunsaturates: the FADS2 gene product DELTA8-desaturates 20:2n-6 and 20:3n-3
J. Lipid Res.
50
1195-1202
2009
Papio anubis (B8R1K0)
brenda
Oura, T.; Kajiwara, S.
Disruption of the sphingolipid DELTA8-desaturase gene causes a delay in morphological changes in Candida albicans
Microbiology
154
3795-3803
2008
Candida albicans
brenda
Habel, A.; Sperling, P.; Bartram, S.; Heinz, E.; Boland, W.
Conformational studies on the DELTA8(E,Z)-sphingolipid desaturase from Helianthus annuus with chiral fluoropalmitic acids as mechanistic probes
J. Org. Chem.
75
4975-4982
2010
Helianthus annuus
brenda
Li, S.F.; Song, L.Y.; Zhang, G.J.; Yin, W.B.; Chen, Y.H.; Wang, R.R.; Hu, Z.M.
Newly identified essential amino acid residues affecting DELTA8-sphingolipid desaturase activity revealed by site-directed mutagenesis
Biochem. Biophys. Res. Commun.
416
165-171
2011
Brassica rapa
brenda
Nagano, M.; Ishikawa, T.; Ogawa, Y.; Iwabuchi, M.; Nakasone, A.; Shimamoto, K.; Uchimiya, H.; Kawai-Yamada, M.
Arabidopsis Bax inhibitor-1 promotes sphingolipid synthesis during cold stress by interacting with ceramide-modifying enzymes
Planta
240
77-89
2014
Arabidopsis thaliana (Q3EBF7), Arabidopsis thaliana (Q9ZRP7), Arabidopsis thaliana Col-0 (Q3EBF7), Arabidopsis thaliana Col-0 (Q9ZRP7)
brenda
Zhou, Y.; Zeng, L.; Fu, X.; Mei, X.; Cheng, S.; Liao, Y.; Deng, R.; Xu, X.; Jiang, Y.; Duan, X.; Baldermann, S.; Yang, Z.
The sphingolipid biosynthetic enzyme sphingolipid delta8 desaturase is important for chilling resistance of tomato
Sci. Rep.
6
38742
2016
Solanum lycopersicum
brenda