Efficient biosynthesis of vanillylamine via biological transamination of lignin-derived vanillin in a β-cyclodextrin-water medium

• Published in: Sustainable chemistry and pharmacy 2024-04, Vol.38, p.101437, Article 101437
• Main Authors: Li, Qi, Kong, Linghui, He, Yu-Cai, Ma, Cuiluan
• Format: Article
• Language: English
• Subjects: amino acids; biosynthesis; energy; Escherichia coli; green chemistry; hydrogen bonding; ligands; lignin; Transaminase; transamination; Vanillin; Vanillylamine; β-Cyclodextrin
• ISSN: 2352-5541; 2352-5541
• DOI: 10.1016/j.scp.2024.101437

Vanillylamine (VALA) emerges as a crucial intermediate in the production of diverse aromatic compounds. Nevertheless, achieving its biocatalytic synthesis efficiently poses a significant challenge. This study presented a novel biological strategy to enhance the upgrading of vanillin (VAL) into VALA. Recombinant E. coli CVTA cells demonstrated notable transamination activity. Molecular docking simulation predicted the VAL ligand displayed a binding energy of −4.75 kcal/mol at the binding site of ω-transaminase (CVTA), forming four hydrogen-bonds with interacting amino acid residues of Tyr223, Trp222 and Val270. Under conditions of pH 8.0 and 35 °C, coupled with the presence of Sn4+ (0.25 mM), VALA yields ranged from 42.7% to 57.5% from 75 to 100 mM VAL in an aqueous medium. Introduction of β-cyclodextrin (β-CD) notably amplified the transamination efficiency, resulting in VALA yields of 81.3%–96.4% under the optimal β-CD-water medium supplemented with Sn4+ (0.25 mM) and 75–100 mM VAL. The integration of β-CD and Sn4+ in this bioreaction system offered an environment-friendly and efficient approach for producing VALA through whole-cell biological transamination, thereby providing a promising pathway for upgrading lignin-derived VAL. The findings of this study carried substantial implications for the development of sustainable and efficient methods to valorize lignin derivatives. [Display omitted] •Lignin-derived vanillylamine was synthesized via a sustainable bioamination.•Recombinant E. coli CVTA cells aminated vanillin into vanillylamine.•Biological amination of vanillin was developed in a β-Cyclodextrin−H2O system.•75 mM vanillin was aminated to vanillylamine (96.4% yield) in β-cyclodextrin−H2O.•The addition of β-cyclodextrin apparently enhanced the transamination efficiency.