氨解
化学
催化作用
酰胺
酰化
生物催化
脂肪酶
有机化学
绿色化学
酶
甘氨酸
甘油
水溶液
脂肪酸
组合化学
氨基酸
生物化学
反应机理
作者
Glen Kai Bin Kua,Giang K. T. Nguyen,Zhi Li
标识
DOI:10.1002/anie.202217878
摘要
Amide syntheses remain a key challenging green chemistry reaction. For instance, green synthesis of N-acyl glycines as biosurfactants and therapeutics is highly desirable to replace chemical pathways using toxic phosgene. Herein, we report a novel concept for enzymatic amidation in an aqueous system via glycerol activation of fatty acids and theirsubsequent aminolysis with glycine to synthesize N-acyl glycines. We then engineer an enzyme (proRML) by reshaping its catalytic pocket to enhance its aminolysis activity and catalytic efficiency by 103-fold and 465-fold, respectively. The evolved proRML (D156S/L258K/L267N/S83D/L58K/R86K/W88V) catalyzed the amidation of a fatty acid with glycine to give N-lauroylglycine with high yield (80 %). It accepts a broad range of medium- to long-chain fatty acids (C8 -C18 ), giving high yields of N-decanoyl-, N-myristoyl-, and N-oleoylglycine. The developed amidation concept may be general, and the engineered enzyme is useful for the green synthesis of N-acyl glycines.
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