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- Name help_outline Nα-formyl-L-methionyl-L-alanyl-L-serine Identifier CHEBI:233102 Charge -1 Formula C12H20N3O6S InChIKeyhelp_outline FRPHJRVMOFQLPK-CIUDSAMLSA-M SMILEShelp_outline C(=O)([C@H](C)NC([C@@H](NC([H])=O)CCSC)=O)N[C@H](C(=O)[O-])CO 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 H2O Identifier CHEBI:15377 (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 6,485 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline L-alanyl-L-serine Identifier CHEBI:233101 Charge 0 Formula C6H12N2O4 InChIKeyhelp_outline IPWKGIFRRBGCJO-IMJSIDKUSA-N SMILEShelp_outline C(=O)([C@@H]([NH3+])C)N[C@H](C(=O)[O-])CO 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 Nα-formyl-L-methionine Identifier CHEBI:57809 Charge -1 Formula C6H10NO3S InChIKeyhelp_outline PYUSHNKNPOHWEZ-YFKPBYRVSA-M SMILEShelp_outline [H]C(=O)N[C@@H](CCSC)C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 6 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:83495 | RHEA:83496 | RHEA:83497 | RHEA:83498 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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Purification and characterization of enzymes involved in the degradation of chemotactic N-formyl peptides.
Nguyen K.T., Pei D.
N-Formyl peptides are derived from proteolytic degradation/processing of bacterial and mitochondrial proteins and serve as potent chemoattractants for mammalian phagocytic leukocytes. A response to the chemotactic N-formyl peptides released by commensal bacteria in the gut region could be detrimen ... >> More
N-Formyl peptides are derived from proteolytic degradation/processing of bacterial and mitochondrial proteins and serve as potent chemoattractants for mammalian phagocytic leukocytes. A response to the chemotactic N-formyl peptides released by commensal bacteria in the gut region could be detrimental, leading to unwanted inflammation. Here, two enzymes that act sequentially to degrade N-formyl peptides were purified from the rat intestinal mucosal layer and biochemically characterized. The first enzyme cleaves chemotactic peptide f-MLF to release N-formylmethionine (f-Met) and dipeptide leucylphenylalanine, with a k(cat) value of 14 s(-)(1), a K(M) value of 0.60 mM, and a k(cat)/K(M) value of 22 500 M(-)(1) s(-)(1). In-gel tryptic digestion followed by mass spectral fingerprinting identified the protein as the alpha-N-acylpeptide hydrolase (or acylamino acid-releasing enzyme, EC 3.4.19.1). The second enzyme hydrolyzes N-formylmethionine into formate and methionine with a k(cat) value of 7.9 s(-)(1), a K(M) value of 3.1 mM, and a k(cat)/K(M) value of 2550 M(-)(1) s(-)(1). This protein was identified as the N-acylase IA (or N(alpha)-acyl-l-amino acid amidohydrolase, EC 3.5.1.14). Together, these two enzymes play a protective role in degrading bacterial and mitochondrial N-formylated peptides. << Less
Biochemistry 44:8514-8522(2005) [PubMed] [EuropePMC]
This publication is cited by 9 other entries.