Reaction participants Show >> << Hide
- Name help_outline N-octanoyl-(2S)-hydroxyglycine Identifier CHEBI:142691 Charge -1 Formula C10H18NO4 InChIKeyhelp_outline HBGXZSWRZZHJKJ-VIFPVBQESA-M SMILEShelp_outline C(CCCCCCC)(=O)N[C@H](C([O-])=O)O 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline glyoxylate Identifier CHEBI:36655 (Beilstein: 3903641) help_outline Charge -1 Formula C2HO3 InChIKeyhelp_outline HHLFWLYXYJOTON-UHFFFAOYSA-M SMILEShelp_outline [H]C(=O)C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 80 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline octanamide Identifier CHEBI:142682 (CAS: 629-01-6) help_outline Charge 0 Formula C8H17NO InChIKeyhelp_outline LTHCSWBWNVGEFE-UHFFFAOYSA-N SMILEShelp_outline NC(=O)CCCCCCC 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:58616 | RHEA:58617 | RHEA:58618 | RHEA:58619 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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N-acylglycine amidation: implications for the biosynthesis of fatty acid primary amides.
Wilcox B.J., Ritenour-Rodgers K.J., Asser A.S., Baumgart L.E., Baumgart M.A., Boger D.L., DeBlassio J.L., deLong M.A., Glufke U., Henz M.E., King L. III, Merkler K.A., Patterson J.E., Robleski J.J., Vederas J.C., Merkler D.J.
Bifunctional peptidylglycine alpha-amidating enzyme (alpha-AE) catalyzes the O2-dependent conversion of C-terminal glycine-extended prohormones to the active, C-terminal alpha-amidated peptide and glyoxylate. We show that alpha-AE will also catalyze the oxidative cleavage of N-acylglycines, from N ... >> More
Bifunctional peptidylglycine alpha-amidating enzyme (alpha-AE) catalyzes the O2-dependent conversion of C-terminal glycine-extended prohormones to the active, C-terminal alpha-amidated peptide and glyoxylate. We show that alpha-AE will also catalyze the oxidative cleavage of N-acylglycines, from N-formylglycine to N-arachidonoylglycine. N-Formylglycine is the smallest amide substrate yet reported for alpha-AE. The (V/K)app for N-acylglycine amidation varies approximately 1000-fold, with the (V/K)app increasing as the acyl chain length increases. This effect is largely an effect on the KM,app; the KM,app for N-formylglycine is 23 +/-0.88 mM, while the KM,app for N-lauroylglycine and longer chain N-acylglycines is in the range of 60-90 microM. For the amidation of N-acetylglycine, N-(tert-butoxycarbonyl)glycine, N-hexanoylglycine, and N-oleoylglycine, the rate of O2 consumption is faster than the rate of glyoxylate production. These results indicate that there must be the initial formation of an oxidized intermediate from the N-acylglycine before glyoxylate is produced. The intermediate is shown to be N-acyl-alpha-hydroxyglycine by two-dimensional 1H-13C heteronuclear multiple quantum coherence (HMQC) NMR. << Less
Biochemistry 38:3235-3245(1999) [PubMed] [EuropePMC]
This publication is cited by 12 other entries.