Preparation of 2-hydroxymuconic semialdehyde from catechol by combining enzymatic catalysis with bisulfite nucleophilic addition

• Published in: Journal of environmental chemical engineering Vol. 9; no. 5; p. 105970
• Main Authors: Bai, Xuerui, Nie, Maiqian, Diwu, Zhenjun, Wang, Lei, Nie, Hongyun, Wang, Yan, Zhang, Bo, Yin, Qiuyue
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 01.10.2021
• Subjects: 2-hydroxymuconic semialdehyde; Aldehyde-bisulfite adducts; Box-Behnken design; Catechol; Enzymatic catalysis; Enzymatic catalysis; Catechol; 2-hydroxymuconic semialdehyde; Box-Behnken design; Aldehyde-bisulfite adducts
• ISSN: 2213-3437; 2213-3437
• DOI: 10.1016/j.jece.2021.105970

2-hydroxymuconic semialdehyde (2-HMS) is a versatile intermediate widely used in organic synthesis. However, it is difficult to manufacture 2-HMS by common chemical methods since it has quite a few different functional groups, making it highly reactive and unstable. For the first time, the combination of an enzymatic catalysis with bisulfite addition was used to effectively prepare 2-HMS. Another benefit of the newly developed method is that the aldehyde-bisulfite adduct is much more stable and easier to store for long term. Intracellular enzymes from Pseudomonas stutzeri N2 could quickly and specifically catalyze the conversion of catechol into 2-HMS. The formed 2-HMS was converted to more stable aldehyde-bisulfite adduct via the bisulfite nucleophilic addition. 2-HMS-bisulfite adduct can be readily purified through a simple recrystallization. In the presence of sodium hydroxide, the adduct can be readily converted back to the desired 2-HMS product when needed. The conversion was optimized through the Box-Behnken design. The incubation of the bisulfite adduct with 3 M sodium hydroxide at 50 ℃ for 2 min gave 2-HMS in about 84% yield. The newly established method is considered to environment-friendly and can be easily scaled up for large-scale production. [Display omitted] •Intracellular enzymes from P. stutzeri N2. can quickly cleaved catechol to 2-HMS.•2-HMS was reacted with sodium bisulfite to form stable aldehyde-bisulfite adducts.•2-HMS-bisulfite adducts were readily converted back to 2-HMS by sodium hydroxide.•Using Box-Behnken design to optimize process conditions for high-yielding 2-HMS.