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Selective and catalyst-free oxidation of D-glucose to D-glucuronic acid induced by high-frequency ultrasound

Abstract : This systematic experimental investigation reveals that high-frequency ultrasound irradiation (550 kHz) induced oxidation of D-glucose to glucuronic acid in excellent yield without assistance of any (bio)catalyst. Oxidation is induced thanks to the in situ production of radical species in water. Experiments show that the dissolved gases play an important role in governing the nature of generated radical species and thus the selectivity for glucuronic acid. Importantly, this process yields glucuronic acid instead of glucuronate salt typically obtained via conventional (bio)catalyst routes, which is of huge interest in respect of downstream processing. Investigations using disaccharides revealed that radicals generated by high frequency ultrasound were also capable of promoting tandem hydrolysis/ oxidation reactions. The necessity to diversify our resources and the general trend of reducing our CO 2 footprint have opened opportunities to produce chemicals, materials and fuels from renewable feedstocks. In this context, the sugar platform is now the subject of intense investigations. Despite the fact that many promising routes to valuable bio-based chemicals and fuels have been reported through (bio)catalytic conversion or fermentation of sugars, the industrial deployment of these pathways is often hampered by a lack of productivity and a costly downstream processing. Clearly, the search of novel technologies has become a priority in this field 1. Oxidation of D-glucose to glucuronic acid is a typical example. Glucuronic acid is a highly valuable chemical and one of the organic building blocks of hyaluronic acid whose current worldwide market is estimated to be over $1 billion 2. Glucuronic acid is widely used in pharmaceutical and medicinal chemistry for the synthesis of modified drugs. It is also largely used as an additive in the food industry, as an active compound in the pharmaceutical industry particularly for the preparation of skin-care products, as an antioxidant, and as a precursor for the biosynthesis of ascorbic acid (Vitamin C) 3. Furthermore, it is an intermediate for the production of L-gulonic acid and 6-amino-L-gulonic acid, an interesting building block for the synthesis of fine chemicals, polymers and surfactants 4. Nowadays, the synthesis of D-glucuronic acid is achieved via the enzymatic oxidation of D-glucose at the C6 position by Ustulina deusta bacteria and bacterium industrium var. Hoshigaki under aerobic conditions 4. Microbe separation, low process productivity and selectivity, as well as the disposal/recycling of waste water, are the main current drawbacks. Solid catalysts have also been explored for this reaction. Nonetheless, to date, from D-glucose, noble metal catalysts exhibit very low selectivity for D-glucuronic acid. Supported metal catalysts like platinum or palladium dispersed over carbon indeed preferentially lead to the oxidation of the C1 position of glucose, resulting in the formation of D-gluconic acid 5. D-glucuronic acid was synthesized under air from protected D-glucose
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http://hal.univ-smb.fr/hal-01937964
Contributor : Abdel-Ilah Saber <>
Submitted on : Wednesday, November 28, 2018 - 1:33:48 PM
Last modification on : Wednesday, December 18, 2019 - 12:20:35 PM

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Prince Amaniampong, Ayman Karam, Quang Trinh, Kai Xu, Quang Thang Trinh, et al.. Selective and catalyst-free oxidation of D-glucose to D-glucuronic acid induced by high-frequency ultrasound. Scientific Reports, Nature Publishing Group, 2017, 7 (1), ⟨10.1038/srep40650⟩. ⟨hal-01937964⟩

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