40031-31-0Relevant articles and documents
Design of a synthetic enzyme cascade for the: In vitro fixation of a C1carbon source to a functional C4sugar
Güner, Samed,Pick, André,Sieber, Volker,Wegat, Vanessa
supporting information, p. 6583 - 6590 (2021/09/10)
Realizing a sustainable future requires intensifying the waste stream conversion, such as converting the greenhouse gas carbon dioxide into value-added products. In this paper, we focus on utilizing formaldehyde as a C1 carbon source for enzymatic C-C bond formation. Formaldehyde can be sustainably derived from other C1 feedstocks, and in this work, we designed a synthetic enzyme cascade for producing the functional C4 sugar erythrulose. This involved tailoring the enzyme formolase, which was optimized for fusing formaldehyde, from a three-carbon producer (dihydroxyacetone) to sets of variants with enhanced two-carbon (glycolaldehyde) or four-carbon (erythrulose) activity. To achieve this, a high-throughput combinatorial screening was developed, and every single variant was evaluated in terms of glycolaldehyde, dihydroxyacetone and erythrulose activity. By applying the two most promising variants in an enzyme cascade, we were able to show for the first time production of ERY starting from a C1 carbon source. In addition, we demonstrated that one of our tailored formolase variants was able to convert 25.0 g L-1 glycolaldehyde to 24.6 g L-1 erythrulose (98% theoretical yield) in a fully atom-economic biocatalytic process. This represents the highest achieved in vitro concentration of erythrulose to date.
Efficient Production of Biomass-Derived C4 Chiral Synthons in Aqueous Solution
Lin, Shaoying,Guo, Xiao,Qin, Kai,Feng, Lei,Zhang, Yahong,Tang, Yi
, p. 4179 - 4184 (2017/12/02)
Carbohydrates are expected to replace petroleum and to become the base of industrial chemistry. Chirality is one particular area in which carbohydrates have a special potential advantage over petroleum resources. Herein, we report a catalytic approach for the direct production of d-tetroses [i.e., d-(?)-erythrose and d-(+)-erythrulose] from d-hexoses through a fast retro-aldol process at 190 °C that achieves a yield of 46 % and completely retains the chiral centers in the final chiral synthon. The d-tetrose products were further converted into their derivatives, thereby accomplishing transfer of chirality from natural chiral hexoses to high-value-added chiral chemicals. Our results also suggest that the product distribution for the conversion of d-hexoses was determined by their isomerization and epimerization trends that competed with their corresponding retro-aldol condensation processes.
Catalytic effect of aluminium chloride on the example of the conversion of sugar model compounds
Schwiderski, Martin,Kruse, Andrea
, p. 64 - 70 (2015/04/14)
Abstract In this work, the catalytic effect of the Bronsted acid hydrochloric acid, the Bronsted base sodium hydroxide and the Lewis acid AlCl3 on the conversion of biomass derived carbohydrates is investigated. On the example of the glycolaldehyde conversion, it is shown that the Lewis acid catalyses the ketol-endiol-tautomerism, the dehydration, the retro-aldol-reaction and the benzilic-acid-rearrangement. The main products are C4- and C6-carbohydrates as well as their secondary products 2-hydroxybut-3-enoic acid 1 and several furans. Under the same reaction conditions hydrochloric acid catalyzes mainly the dehydration and sodium hydroxide the tautomerism and subsequent aldolization.
