Enzyme Engineering for High‐Yielding Amide Formation: Lipase‐Catalyzed Synthesis of N‐Acyl Glycines in Aqueous Media

Author:

Kua Glen Kai Bin12ORCID,Nguyen Giang Kien Truc2,Li Zhi1ORCID

Affiliation:

1. Department of Chemical and Biomolecular Engineering National University of Singapore 4 Engineering Drive 4 Singapore, Singapore 117585 Singapore

2. Wilmar International Limited 28 Biopolis Singapore 138568 Singapore

Abstract

AbstractAmide 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.

Funder

Economic Development Board - Singapore

Publisher

Wiley

Subject

General Medicine

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