Facile and Sustainable Synthesis of Commendamide and Its Analogues

Overview

Journal Front Chem

Specialty Chemistry

Date 2022 Mar 18

PMID 35300384

Authors

Rosaria Villano

Francesco Tinto

Vincenzo Di Marzo

Affiliations

Soon will be listed here.

Abstract

Commendamide, or N-(3-hydroxypalmitoyl)-glycine , is a gut microbiota-derived bioactive metabolite, structurally similar to long-chain N-acyl-amino acids which belong to the complex lipid signaling system known as endocannabinoidome and play important roles in mammals through activation of, , G-protein-coupled receptors (GPCRs). In this work, we describe a simple, green and economic method for the preparation of commendamide , a GPCR G2A/132 agonist. The developed protocol is general and could also be applied to the synthesis of deuterated commendamide , as well as to other minor microbiota-derived metabolites, such as the analog .

Citing Articles

A sustainable protocol for the synthesis of -acyl tryptamines, a class of potential gut microbiota-derived endocannabinoid-like mediators.

Villano R, Di Marzo V Front Chem. 2024; 12:1436008.

PMID: 39449691 PMC: 11500036. DOI: 10.3389/fchem.2024.1436008.

Synthesis of -(3-Acyloxyacyl)glycines, Small Molecules with Potential Role in Gut Microbiome-Endocannabinoidome Communication.

Villano R, Di Marzo V Molecules. 2024; 29(15).

PMID: 39125106 PMC: 11313728. DOI: 10.3390/molecules29153703.

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