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- Name help_outline a 1,2-diacyl-sn-glycero-3-phospho-L-serine Identifier CHEBI:57262 Charge -1 Formula C8H11NO10PR2 SMILEShelp_outline [NH3+][C@@H](COP([O-])(=O)OC[C@@H](COC([*])=O)OC([*])=O)C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 47 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline N-(acetyl)-sphing-4-enine Identifier CHEBI:46979 (CAS: 3102-57-6) help_outline Charge 0 Formula C20H39NO3 InChIKeyhelp_outline BLTCBVOJNNKFKC-QUDYQQOWSA-N SMILEShelp_outline CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](CO)NC(C)=O 2D coordinates Mol file for the small molecule Search links Involved in 42 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline a 2-acyl-sn-glycero-3-phospho-L-serine Identifier CHEBI:65214 Charge -1 Formula C7H12NO9PR SMILEShelp_outline [NH3+][C@@H](COP([O-])(=O)OC[C@@H](CO)OC([*])=O)C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 9 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 1-O-acyl-N-(acetyl)-sphing-4-enine Identifier CHEBI:84483 Charge 0 Formula C21H38NO4R SMILEShelp_outline CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](COC([*])=O)NC(C)=O 2D coordinates Mol file for the small molecule Search links Involved in 39 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:78355 | RHEA:78356 | RHEA:78357 | RHEA:78358 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Related reactions help_outline
Specific form(s) of this reaction
Publications
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Determinants of pH profile and acyl chain selectivity in lysosomal phospholipase A2.
Hinkovska-Galcheva V., Kelly R., Manthei K.A., Bouley R., Yuan W., Schwendeman A., Tesmer J.J.G., Shayman J.A.
Lysosomal phospholipase A2 (LPLA<sub>2</sub>) is characterized by broad substrate recognition, peak activity at acidic pH, and the transacylation of lipophilic alcohols, especially <i>N</i>-acetyl-sphingosine. Prior structural analysis of LPLA<sub>2</sub> revealed the presence of an atypical acidi ... >> More
Lysosomal phospholipase A2 (LPLA<sub>2</sub>) is characterized by broad substrate recognition, peak activity at acidic pH, and the transacylation of lipophilic alcohols, especially <i>N</i>-acetyl-sphingosine. Prior structural analysis of LPLA<sub>2</sub> revealed the presence of an atypical acidic residue, Asp13, in the otherwise hydrophobic active site cleft. We hypothesized that Asp13 contributed to the pH profile and/or substrate preference of LPLA<sub>2</sub> for unsaturated acyl chains. To test this hypothesis, we substituted Asp13 for alanine, cysteine, or phenylalanine; then, we monitored the formation of 1-<i>O</i>-acyl-<i>N</i>-acetylsphingosine to measure the hydrolysis of <i>sn</i>-1 versus <i>sn</i>-2 acyl groups on a variety of glycerophospholipids. Substitutions with Asp13 yielded significant enzyme activity at neutral pH (7.4) and perturbed the selectivity for mono- and double-unsaturated acyl chains. However, this position played no apparent role in selecting for either the acyl acceptor or the head group of the glycerophospholipid. Our modeling indicates that Asp13 and its substitutions contribute to the pH activity profile of LPLA<sub>2</sub> and to acyl chain selectivity by forming part of a hydrophobic track occupied by the scissile acyl chain. << Less
J. Lipid Res. 59:1205-1218(2018) [PubMed] [EuropePMC]
This publication is cited by 26 other entries.