RGD Reference Report - N-acylglycine amidation: implications for the biosynthesis of fatty acid primary amides.

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N-acylglycine amidation: implications for the biosynthesis of fatty acid primary amides.
Authors:	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 Merkler, K A Patterson, J E Robleski, J J Vederas, J C Merkler, D J
Citation:	Wilcox BJ, etal., Biochemistry. 1999 Mar 16;38(11):3235-45. doi: 10.1021/bi982255j.
RGD ID:	14390048
Pubmed:	PMID:10079066 (View Abstract at PubMed)
DOI:	DOI:10.1021/bi982255j (Journal Full-text)
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.

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Biological Process

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Object Symbol	Species	Term	Qualifier	Evidence	With	Notes	Source	Original Reference(s)
Pam	Rat	fatty acid primary amide biosynthetic process	involved_in	IDA		PMID:10079066	UniProt
Pam	Rat	peptide amidation	involved_in	IDA		PMID:10079066	UniProt

Molecular Function

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Object Symbol	Species	Term	Qualifier	Evidence	With	Notes	Source	Original Reference(s)
Pam	Rat	peptidylamidoglycolate lyase activity	enables	IDA		PMID:10079066	UniProt
Pam	Rat	peptidylglycine monooxygenase activity	enables	IDA		PMID:10079066	UniProt

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Genes (Rattus norvegicus)

Pam (peptidylglycine alpha-amidating monooxygenase)

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N-acylglycine amidation: implications for the biosynthesis of fatty acid primary amides.