Reaction participants Show >> << Hide
- Name help_outline 11-cis-retinol Identifier CHEBI:16302 (CAS: 22737-96-8) help_outline Charge 0 Formula C20H30O InChIKeyhelp_outline FPIPGXGPPPQFEQ-IOUUIBBYSA-N SMILEShelp_outline CC(/C=C\C=C(C)\C=C\C1=C(C)CCCC1(C)C)=C\CO 2D coordinates Mol file for the small molecule Search links Involved in 12 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline tetradecanoyl-CoA Identifier CHEBI:57385 Charge -4 Formula C35H58N7O17P3S InChIKeyhelp_outline DUAFKXOFBZQTQE-QSGBVPJFSA-J SMILEShelp_outline CCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n1cnc2c(N)ncnc12 2D coordinates Mol file for the small molecule Search links Involved in 43 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 11-cis-retinyl tetradecanoate Identifier CHEBI:138676 Charge 0 Formula C34H56O2 InChIKeyhelp_outline WIYYXLSPNGTKOH-IIFYKUDISA-N SMILEShelp_outline C1(/C=C/C(=C/C=C\C(=C\COC(CCCCCCCCCCCCC)=O)\C)/C)=C(C)CCCC1(C)C 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 CoA Identifier CHEBI:57287 (Beilstein: 11604429) help_outline Charge -4 Formula C21H32N7O16P3S InChIKeyhelp_outline RGJOEKWQDUBAIZ-IBOSZNHHSA-J SMILEShelp_outline CC(C)(COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n1cnc2c(N)ncnc12)[C@@H](O)C(=O)NCCC(=O)NCCS 2D coordinates Mol file for the small molecule Search links Involved in 1,511 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:55272 | RHEA:55273 | RHEA:55274 | RHEA:55275 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Related reactions help_outline
More general form(s) of this reaction
Publications
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Allosteric modulation of the substrate specificity of acyl-CoA wax alcohol acyltransferase 2.
Arne J.M., Widjaja-Adhi M.A., Hughes T., Huynh K.W., Silvaroli J.A., Chelstowska S., Moiseenkova-Bell V.Y., Golczak M.
The esterification of alcohols with fatty acids is a universal mechanism to form inert storage forms of sterols, di- and triacylglycerols, and retinoids. In ocular tissues, formation of retinyl esters is an essential step in the enzymatic regeneration of the visual chromophore (11-<i>cis</i>-retin ... >> More
The esterification of alcohols with fatty acids is a universal mechanism to form inert storage forms of sterols, di- and triacylglycerols, and retinoids. In ocular tissues, formation of retinyl esters is an essential step in the enzymatic regeneration of the visual chromophore (11-<i>cis</i>-retinal). Acyl-CoA wax alcohol acyltransferase 2 (AWAT2), also known as multifunctional <i>O</i>-acyltransferase (MFAT), is an integral membrane enzyme with a broad substrate specificity that has been shown to preferentially esterify 11-<i>cis</i>-retinol and thus contribute to formation of a readily available pool of <i>cis</i> retinoids in the eye. However, the mechanism by which this promiscuous enzyme can gain substrate specificity is unknown. Here, we provide evidence for an allosteric modulation of the enzymatic activity by 11-<i>cis</i> retinoids. This regulation is independent from cellular retinaldehyde-binding protein (CRALBP), the major <i>cis</i>-retinoid binding protein. This positive-feedback regulation leads to decreased esterification rates for 9-<i>cis</i>, 13-<i>cis</i>, or all-<i>trans</i> retinols and thus enables preferential synthesis of 11-<i>cis</i>-retinyl esters. Finally, electron microscopy analyses of the purified enzyme indicate that this allosteric effect does not result from formation of functional oligomers. Altogether, these data provide the experimental basis for understanding regulation of AWAT2 substrate specificity. << Less
J. Lipid Res. 58:719-730(2017) [PubMed] [EuropePMC]
This publication is cited by 6 other entries.