Synthesis of Syringaresinol

Syringaresinol 是一种天然存在的化合物，具有多种应用，包括作为双酚A（BPA）的绿色和安全替代品。以下是关于Syringaresinol合成的详细信息：

酶催化合成

Syringaresinol可以通过酶催化合成，这种方法具有选择性、高效性和环保性。研究表明，通过使用eugenol oxidase (EUGO) 和 horseradish peroxidase (HRP) 的组合，可以从2,6-dimethoxy-4-allylphenol进行一锅法转化合成Syringaresinol1567。此外，通过结构启发的酶工程，产生了I427A EUGO突变体，显著提高了2,6-dimethyltryptophanol的效率1。

一锅法合成

一锅法合成Syringaresinol的方法已被优化，通过串联氧化酶和过氧化物酶步骤，实现了高产量的Syringaresinol合成1520。这种方法不仅提高了合成效率，而且通过使用相对便宜的起始材料，降低了成本672223。

从木质素衍生酚合成

Syringaresinol也可以从木质素衍生的酚类化合物通过还原催化裂化合成。这种方法符合循环生物经济的需求，为可再生、基于生物的化学品提供了一种生产方式1013。

优化合成条件

为了提高Syringaresinol的合成效率，研究人员对一锅法、两酶合成的条件进行了优化。通过调整反应时间和温度，以及使用微波辐射等技术，可以显著缩短反应时间并提高产率24。

应用

Syringaresinol不仅在化学合成领域有应用，还在生物活性和材料科学中显示出潜力。例如，Syringaresinol被提出作为双酚A的替代品，用于非异氰酸酯聚氨酯（NIPU）的合成22125。此外，Syringaresinol还显示出良好的热稳定性和抗氧化活性，可以在不经过进一步纯化的情况下直接用于与聚合物合成相关的多种应用14。

结论

Syringaresinol的合成方法多样，包括酶催化合成、一锅法合成和从木质素衍生酚合成等。这些方法不仅提高了合成效率，而且有助于实现更环保、更可持续的化学生产过程。随着对Syringaresinol应用的不断探索，其在生物经济中的重要性将日益凸显。

What are the key advantages of using the I427A EUGO mutant in the synthesis of syringaresinol?

The I427A EUGO mutant has been engineered to enhance the performance of eugenol oxidase (EUGO) on 2,6-dimethoxy-4-allylphenol, which is a key step in the synthesis of syringaresinol. The key advantages of using this mutant include its significantly improved efficiency in the one-pot conversion process that includes both EUGO and horseradish peroxidase (HRP)167. This improvement is attributed to the structure-inspired enzyme engineering that led to the creation of the I427A EUGO mutant, which is more effective with 2,6-dimethyltryptophanol1. The use of this mutant contributes to a more efficient and potentially more cost-effective production of syringaresinol.

How does the use of syringaresinol as a replacement for bisphenol A in NIPUs contribute to a circular bioeconomy?

Syringaresinol, derived from sinapic acid, is proposed as a greener and safer alternative to the petro-sourced and toxic bisphenol A (BPA)225. The use of syringaresinol in Non-Isocyanate PolyUrethanes (NIPUs) synthesis aligns with the principles of a circular bioeconomy by utilizing a renewable resource. This shift supports the development of a sustainable and eco-friendly chemical industry that reduces reliance on petroleum-based products and minimizes environmental impact. Furthermore, the synthesis of a five-membered cyclic carbonate SYR-CC from syringaresinol demonstrates its potential for various applications, further promoting the use of bio-based materials in place of traditional petroleum-derived chemicals2.

What are the specific applications of the five-membered cyclic carbonate SYR-CC derived from syringaresinol?

The five-membered cyclic carbonate SYR-CC, derived from syringaresinol, has been prepared and is considered for use in the synthesis of nonisocyanate polyurethane (NIPU)2125. This cyclic carbonate is a valuable intermediate in the synthesis of various polymers and other chemical products due to its unique structure and reactivity. It can be used as a building block in the production of bio-based chemicals and materials, contributing to the development of a circular bioeconomy and offering a renewable alternative to petroleum-based chemicals25.

What are the stereoselective modes involved in the formation of both (+)- and (-)-enantiomers of syringaresinol?

Syringaresinol can be formed through the coupling of sinapyl alcohol with stereoselective modes, resulting in the production of both (+)- and (-)-enantiomers16. The stereoselective modes refer to the specific pathways or mechanisms by which the enantiomers are formed, ensuring that the stereochemistry of the product is controlled and predictable. This is crucial in the synthesis of biologically active compounds, as the stereochemistry can significantly influence the biological activity and properties of the resulting molecules.

How does the biocatalytic synthesis of syringaresinol using eugenol oxidase (EUGO) and horseradish peroxidase (HRP) compare to traditional chemical synthesis methods in terms of efficiency and environmental impact?

The biocatalytic synthesis of syringaresinol using eugenol oxidase (EUGO) and horseradish peroxidase (HRP) offers a more selective, efficient, and eco-friendly process compared to traditional chemical synthesis methods51113141520222355. This method allows for a one-pot conversion with high yields and does not require the use of hazardous chemicals or high energy consumption typically associated with traditional synthesis. The biocatalytic approach also contributes to waste reduction and the overall sustainability of the production process. Furthermore, the use of relatively cheap starting materials, such as 2,6-dimethoxy-4-allylphenol, makes the process more economically viable67112223. The enzymatic synthesis of syringaresinol has been optimized for multigram scale production, demonstrating its potential for industrial application11.