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Literature summary extracted from

  • 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 (2010), J. Org. Chem., 75, 4975-4982.
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.14.19.4 expressed in yeast cells Helianthus annuus
1.14.19.29 expressed in Saccharomyces cerevisiae Helianthus annuus

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.14.19.29 (4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+ Helianthus annuus
-
 (4R,8E)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
 ?
1.14.19.29 (4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+ Helianthus annuus
-
 (4R,8Z)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.14.19.4 Helianthus annuus
-
-
-
1.14.19.29 Helianthus annuus
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.19.4 (R)-9-fluorophytosphinganine + reduced acceptor + O2 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 Helianthus annuus (Z)-9-fluoro-8-phytosphingenine + acceptor + H2O
-
 ?
1.14.19.4 (S)-8-fluorophytosphinganine + reduced acceptor + O2 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 Helianthus annuus (Z)-8-fluoro-8-phytosphingenine + acceptor + H2O
-
 ?
1.14.19.4 (S)-9-fluorophytosphinganine + reduced acceptor + O2 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 Helianthus annuus (E)-9-fluoro-8-phytosphingenine + acceptor + H2O
-
 ?
1.14.19.4 additional information (R)-8-fluorophytosphinganine does not yield any desaturation product Helianthus annuus ?
-
 ?
1.14.19.29 (4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
-
 Helianthus annuus (4R,8E)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
 ?
1.14.19.29 (4R)-4-hydroxysphinganine ceramide + ferrocytochrome b5 + O2 + H+
-
 Helianthus annuus (4R,8Z)-4-hydroxysphing-8-enine ceramide + ferricytochrome b5 + H2O
-
 ?
1.14.19.29 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 Helianthus annuus ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.14.19.4 DELTA8-sphingolipid desaturase
-
 Helianthus annuus
1.14.19.29 DELTA8(E,Z)-sphingolipid desaturase
-
 Helianthus annuus

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.14.19.4 28
-
 assay at Helianthus annuus

Cofactor

EC Number Cofactor Comment Organism Structure
1.14.19.29 cytochrome b5
-
 Helianthus annuus