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Literature summary for 1.14.19.4 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)

Cloned (Comment) Organism
expressed in yeast cells Helianthus annuus

Organism

Organism UniProt Comment Textmining
Helianthus annuus
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-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(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
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?
(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
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?
(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
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?
additional information (R)-8-fluorophytosphinganine does not yield any desaturation product Helianthus annuus ?
-
?

Synonyms

Synonyms Comment Organism
DELTA8-sphingolipid desaturase
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Helianthus annuus

Temperature Optimum [°C]

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