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- Name help_outline N-dodecanoyl-heptadecasphing-4-enine-1-phosphoethanolamine Identifier CHEBI:143864 Charge 0 Formula C31H63N2O6P InChIKeyhelp_outline ZIEWVPJUBVRCAL-DQBIDPIGSA-N SMILEShelp_outline C(CCCCCCCCC)CC\C=C\[C@@H](O)[C@@H](NC(=O)CCCCCCCCCCC)COP(OCC[NH3+])(=O)[O-] 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline ethanolamine Identifier CHEBI:57603 Charge 1 Formula C2H8NO InChIKeyhelp_outline HZAXFHJVJLSVMW-UHFFFAOYSA-O SMILEShelp_outline [NH3+]CCO 2D coordinates Mol file for the small molecule Search links Involved in 44 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline N-dodecanoyl-heptadecasphing-4-enine-1,3-cyclic phosphate Identifier CHEBI:143865 Charge -1 Formula C29H55NO5P InChIKeyhelp_outline WCWADZSYRHRKHD-LVDQGNEYSA-M SMILEShelp_outline C(CCCCCCCCC)CC\C=C\[C@@H]1[C@@H](NC(=O)CCCCCCCCCCC)COP(=O)(O1)[O-] 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:60616 | RHEA:60617 | RHEA:60618 | RHEA:60619 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Related reactions help_outline
More general form(s) of this reaction
Publications
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Variable substrate preference among phospholipase D toxins from Sicariid spiders.
Lajoie D.M., Roberts S.A., Zobel-Thropp P.A., Delahaye J.L., Bandarian V., Binford G.J., Cordes M.H.
Venoms of the sicariid spiders contain phospholipase D enzyme toxins that can cause severe dermonecrosis and even death in humans. These enzymes convert sphingolipid and lysolipid substrates to cyclic phosphates by activating a hydroxyl nucleophile present in both classes of lipid. The most medica ... >> More
Venoms of the sicariid spiders contain phospholipase D enzyme toxins that can cause severe dermonecrosis and even death in humans. These enzymes convert sphingolipid and lysolipid substrates to cyclic phosphates by activating a hydroxyl nucleophile present in both classes of lipid. The most medically relevant substrates are thought to be sphingomyelin and/or lysophosphatidylcholine. To better understand the substrate preference of these toxins, we used (31)P NMR to compare the activity of three related but phylogenetically diverse sicariid toxins against a diverse panel of sphingolipid and lysolipid substrates. Two of the three showed significantly faster turnover of sphingolipids over lysolipids, and all three showed a strong preference for positively charged (choline and/or ethanolamine) over neutral (glycerol and serine) headgroups. Strikingly, however, the enzymes vary widely in their preference for choline, the headgroup of both sphingomyelin and lysophosphatidylcholine, versus ethanolamine. An enzyme from Sicarius terrosus showed a strong preference for ethanolamine over choline, whereas two paralogous enzymes from Loxosceles arizonica either preferred choline or showed no significant preference. Intrigued by the novel substrate preference of the Sicarius enzyme, we solved its crystal structure at 2.1 Å resolution. The evolution of variable substrate specificity may help explain the reduced dermonecrotic potential of some natural toxin variants, because mammalian sphingolipids use primarily choline as a positively charged headgroup; it may also be relevant for sicariid predatory behavior, because ethanolamine-containing sphingolipids are common in insect prey. << Less
J. Biol. Chem. 290:10994-11007(2015) [PubMed] [EuropePMC]
This publication is cited by 7 other entries.