Marrs Kevin, Vuong Thu V, Master Emma R
Department of Chemical Engineering and Applied Chemistry, University of Toronto, 200 College Street, Toronto, Ontario, M5S 3E5, Canada.
Department of Bioproducts and Biosystems, Aalto University, Kemistintie 1, 02150, Espoo, Finland.
Chembiochem. 2025 Mar 15;26(6):e202400985. doi: 10.1002/cbic.202400985. Epub 2025 Jan 20.
This study describes an enzymatic pathway to produce high purity 4-O-methylglucaric acid from xylan, an underutilized fraction of lignocellulosic biomass. Beechwood xylan was enzymatically hydrolysed using a commercial xylanase and an α-glucuronidase from Amphibacillus xylanus to form 4-O-methylglucuronic acid, which was then purified by anion exchange chromatography and subsequently oxidized to 4-O-methylglucaric acid using a recombinantly produced uronic acid oxidase from Citrus sinensis. Enzymatic oxidation with uronic acid oxidase afforded 95 % yield in 72 hours which is considerably higher than yields previously achieved using a glucooligosaccharide oxidase from Sarocladium strictum. 4-O-methylglucaric acid was isolated by precipitation and purified by recrystallization. Characterization by liquid chromatography mass spectrometry and nuclear magnetic resonance spectroscopy confirmed product identity and high purity (97.8 % w/w). 4-O-methylglucaric acid's performance as a detergent builder was compared to commercial glucaric acid. At 10 : 1 molar ratios of detergent builder to calcium, 4-O-methylglucaric acid provided similar calcium sequestration performance to glucaric acid (less than 5 % difference) at pH 7 and pH 10 in the presence of surfactants, including sodium dodecylbenzene sulfonate. Given their similar calcium sequestration performance, 4-O-methylglucaric acid could effectively substitute for glucaric acid in detergent formulations.
本研究描述了一种从木聚糖生产高纯度4-O-甲基葡糖二酸的酶促途径，木聚糖是木质纤维素生物质中未被充分利用的部分。使用商业木聚糖酶和来自嗜碱栖热放线菌的α-葡糖醛酸酶对山毛榉木聚糖进行酶促水解，以形成4-O-甲基葡糖醛酸，然后通过阴离子交换色谱法进行纯化，随后使用重组生产的来自脐橙的糖醛酸氧化酶将其氧化为4-O-甲基葡糖二酸。用糖醛酸氧化酶进行酶促氧化在72小时内产率达到95%，这大大高于先前使用来自紧密帚霉的低聚葡萄糖氧化酶所获得的产率。通过沉淀分离4-O-甲基葡糖二酸，并通过重结晶进行纯化。通过液相色谱质谱和核磁共振光谱进行表征，确认了产物的身份和高纯度（97.8% w/w）。将4-O-甲基葡糖二酸作为洗涤剂助洗剂的性能与商业葡糖二酸进行了比较。在洗涤剂助洗剂与钙的摩尔比为10∶1时，在pH 7和pH 10且存在表面活性剂（包括十二烷基苯磺酸钠）的情况下，4-O-甲基葡糖二酸提供了与葡糖二酸相似的钙螯合性能（差异小于5%）。鉴于它们相似的钙螯合性能，4-O-甲基葡糖二酸可以在洗涤剂配方中有效替代葡糖二酸。
