Reaction participants Show >> << Hide
- Name help_outline L-ascorbate Identifier CHEBI:38290 (Beilstein: 3549814; CAS: 299-36-5) help_outline Charge -1 Formula C6H7O6 InChIKeyhelp_outline CIWBSHSKHKDKBQ-JLAZNSOCSA-M SMILEShelp_outline [H][C@@]1(OC(=O)C(O)=C1[O-])[C@@H](O)CO 2D coordinates Mol file for the small molecule Search links Involved in 34 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline N-(9Z-octadecenoyl)glycine Identifier CHEBI:133992 Charge -1 Formula C20H36NO3 InChIKeyhelp_outline HPFXACZRFJDURI-KTKRTIGZSA-M SMILEShelp_outline C(\CCCCCCCC(=O)NCC([O-])=O)=C\CCCCCCCC 2D coordinates Mol file for the small molecule Search links Involved in 3 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline O2 Identifier CHEBI:15379 (CAS: 7782-44-7) help_outline Charge 0 Formula O2 InChIKeyhelp_outline MYMOFIZGZYHOMD-UHFFFAOYSA-N SMILEShelp_outline O=O 2D coordinates Mol file for the small molecule Search links Involved in 2,648 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H2O Identifier CHEBI:15377 (Beilstein: 3587155; CAS: 7732-18-5) help_outline Charge 0 Formula H2O InChIKeyhelp_outline XLYOFNOQVPJJNP-UHFFFAOYSA-N SMILEShelp_outline [H]O[H] 2D coordinates Mol file for the small molecule Search links Involved in 6,048 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline monodehydro-L-ascorbate radical Identifier CHEBI:59513 Charge -1 Formula C6H6O6 InChIKeyhelp_outline LHFJOBMTAJJOTB-JLAZNSOCSA-M SMILEShelp_outline [H][C@@]1(OC(=O)C([O-])=C1[O])[C@@H](O)CO 2D coordinates Mol file for the small molecule Search links Involved in 16 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline N-(9Z-octadecenoyl)-(2S)-hydroxyglycine Identifier CHEBI:142696 Charge -1 Formula C20H36NO4 InChIKeyhelp_outline QFZBGCAHQGWTGN-VJIACCKLSA-M SMILEShelp_outline C(\CCCCCCCC(=O)N[C@H](C([O-])=O)O)=C\CCCCCCCC 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
Cross-references
| RHEA:58600 | RHEA:58601 | RHEA:58602 | RHEA:58603 | |
|---|---|---|---|---|
| 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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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.