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, 8 (4), 156-165

N-FATTY ACYLGLYCINES: UNDERAPPRECIATED ENDOCANNABINOID-LIKE FATTY ACID AMIDES?

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N-FATTY ACYLGLYCINES: UNDERAPPRECIATED ENDOCANNABINOID-LIKE FATTY ACID AMIDES?

Ryan L Anderson et al. J Biol Nat.

Abstract

Long-chain N-fatty acylglycines, R-CO-NH-CH2-COOH (where "R" refers to an unsaturated or saturated alkyl chain of at least 14 carbons) are found in mammals and insects and are structurally related to the cell-signaling, lipid-like, N-fatty acylethanolamines, R-CO-NH-CH2-CH2-OH (where "R" refers to an alkyl chain of at least 14 carbons). Accumulating evidence demonstrates that the N-fatty acylglycines have important cellular functions, but much work remains in order to fully appreciate and understand these biomolecules including: (a) more work on their functions in vivo, (b) measuring their concentrations in the cell, (c) defining the pathways for the biosynthesis and degradation, and (d) understanding the metabolic interconversion(s) between the N-fatty acylglycines and other fatty acid amides. The purpose of reviewing the current state-of-knowledge about the N-fatty acylglycines is to stimulate future research about this intriguing family of biomolecules.

Keywords: N-arachidonoylglycine; N-fatty acylethanolamine; N-fatty acylglycine; N-linoleoylglycine; N-myrisotylglycine; N-oleoylglycine; N-palmitoylglycine; fatty acid amide hydrolase; glycine N-acyltransferase (GLYAT); metabolic interconversion; oxidative metabolism.

Conflict of interest statement

COMPETING INTERESTS Authors have declared that no competing interests exist.

Figures

Fig. 1
Fig. 1
N-Fatty Acylglycine Biosynthesis. The number in the brackets refer to the appropriate references for the individual reactions
Fig. 2
Fig. 2
The PAM-mediated Oxidation of N-Fatty Acylglycines to the Primary Fatty Acid Amides.
Fig. 3
Fig. 3
The Cytochrome P450 BM-3 PAM-mediated Oxidation of N-Palmitoylglycine.
Fig. 4
Fig. 4
The Oxidative Metabolism of N-Arachidonoylglycine. COX-2 is cyclooxygenase-2, 12-LOX is 12-lipoxygenase, and 15-LOX is 15-lipoxygenase

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