Beilstein J. Org. Chem.2016,12, 2256–2266, doi:10.3762/bjoc.12.218
Fabio Arico Pietro Tundo Department of Environmental Sciences, Informatics and Statistics, Ca’ Foscari University, Scientific Campus Via Torino 155 , 30170 Venezia Mestre, Italy 10.3762/bjoc.12.218 Abstract In this review the reactivity of the bio-based platform compounds D-sorbitol and
isosorbide with green reagents and solvent dimethyl carbonate (DMC) is reported. Dehydration of D-sorbitol via DMC in the presence of catalytic amounts of base is an efficient and viable process for the preparation of the industrially relevant anhydro sugar isosorbide. This procedure is “chlorine-free”, one
reactivity of isosorbide and the non-toxic properties of DMC represent indeed a green match leading to several industrial appealing potential applications.
Keywords: carbohydrate chemistry; D-sorbitol; dimethyl carbonate; green chemistry; isosorbide; Review
Introduction
In the last twenty years biorefinery
Beilstein J. Org. Chem.2013,9, 2434–2445, doi:10.3762/bjoc.9.281
sanctum seeds) and investigated their synthetic application for L-glucose production from D-sorbitol (Scheme 13) [83][84]. Catalase could degrade the hydrogen peroxide byproduct and increase the conversion by removing the inhibition effect of hydrogen peroxide toward galactose oxidase and regenerating
-talitol catalyzed by a halotolerant yeast strain Candida famata R28 could be significantly increased in the presence of various carbohydrates such as erythritol, D-sorbitol, ribitol and glycerol in the reaction mixture [100]. The faster consumption of the substrate could be explained by the in situ NADH
regeneration while those supplementary carbohydrates are oxidized by a dehydrogenase. At 10% substrate concentration, the conversion rate could reach as high as 95% catalyzed by whole cells supplemented with 5% of D-sorbitol [100]. In addition, this bioconversion/reduction could also be carried out by various
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Graphical Abstract
Scheme 1:
Synthesis of D-tagatose from D-galactose using L-arabinose isomerase.