Dipartimento di Scienze Biomediche e Cliniche, Università degli Studi di Milano, Via G.B. Grassi 74, 20157 Milano, Italy.
Dipartimento di Scienze Biomediche, Chirurgiche e Odontoiatriche, Università degli Studi di Milano, Via della Commenda 10, 20122 Milano, Italy.
Molecules. 2022 Aug 15;27(16):5190. doi: 10.3390/molecules27165190.
A simple and practical synthesis of 2-arachidonoyl glycerol (2-AG), an endogenous agonist for cannabinoid receptors, based on a two-step enzymatic process and a chemical coupling, was achieved with a good yield and negligible amount of the isomerization product 1-AG. Commercial preparation of immobilized lipase from (MML) was selected as the most suitable enzyme to catalyze the efficient protection of glycerol using vinyl benzoate as an acyl transfer reagent in tetrahydrofuran. The same enzyme was used to remove the protective groups in positions 1 and 3. Owing to the mild neutral conditions and easy suitability of the method, 2-AG was obtained without any isomerization to the more stable 1-AG and air oxidation of acid chain. The synthetic method proposed here allows us to easily obtain 2-AG from the protected precursor in a one-step reaction without purification requirement.
基于两步酶法和化学偶联反应，实现了大麻素受体内源性激动剂 2-花生四烯酸甘油（2-AG）的简单实用的合成，具有良好的收率和可忽略不计的异构化产物 1-AG。选择商业制备的固定化脂肪酶（MML）作为最适合的酶，使用苯乙烯作为酰基转移试剂，在四氢呋喃中高效保护甘油。同样的酶被用来去除 1 位和 3 位的保护基团。由于该方法条件温和、中性，且易于适应，因此在没有异构化为更稳定的 1-AG 和酸链空气氧化的情况下获得了 2-AG。所提出的合成方法允许我们从保护前体中一步反应轻松获得 2-AG，无需纯化要求。
