14807-05-7Relevant articles and documents
Base catalysed isomerisation of aldoses of the arabino and lyxo series in the presence of aluminate
Ekeberg, Dag,Morgenlie, Svein,Stenstrom, Yngve
, p. 779 - 786 (2002)
Base-catalysed isomerisation of aldoses of the arabino and lyxo series in aluminate solution has been investigated. L-Arabinose and D-galactose give L-erythro-2-pentulose (L-ribulose) and D-lyxo-2-hexulose (D-tagatose), respectively, in good yields, whereas lower reactivity is observed for 6-deoxy-D-galactose (D-fucose). From D-lyxose, D-mannose and 6-deoxy-L-mannose (L-rhamnose) are obtained mixtures of ketoses and C-2 epimeric aldoses. Small amounts of the 3-epimers of the ketoses were also formed. 6-Deoxy-L-arabino-2-hexulose (6-deoxy-L-fructose) and 6-deoxy-L-glucose (L-quinovose) were formed in low yields from 6-deoxy-L-mannose and isolated as their O-isopropylidene derivatives. Explanations of the differences in reactivity and course of the reaction have been suggested on the basis of steric effects.
Production of l-rhamnulose, a rare sugar, from l-rhamnose using commercial immobilized glucose isomerase
Kim, Yeong-Su,Kim, Do-Yeon,Park, Chang-Su
, p. 417 - 421 (2018)
A commercial immobilized d-glucose isomerase from Streptomyces murines (Sweetzyme) was used to produce l-rhamnulose from l-rhamnose in a packed-bed reactor. The optimal conditions for l-rhamnulose production from l-rhamnose were determined as pH 8.0, 60 °C, 300 g?L?1 l-rhamnose as a substrate, and 0.6 h?1 dilution rate. The half-life of the immobilized enzyme at 60 °C was 809 h. Under the optimal conditions, the immobilized enzyme produced an average of 135 g?L?1 l-rhamnulose from 300 g?L?1 l-rhamnose after 16 days at pH 8.0, 60 °C, and 0.6 h?1 dilution rate, with a productivity of 81 g/L/h and a conversion yield of 45% in a packed-bed reactor.
Bioproduction of a novel sugar 1-deoxy-l-fructose by Enterobacter aerogenes IK7; isomerization of a 6-deoxyhexose to a 1-deoxyhexose
Gullapalli, Pushpakiran,Shiji, Takayuki,Rao, Devendar,Yoshihara, Akihide,Morimoto, Kenji,Takata, Goro,Fleet, George W.J.,Izumori, Ken
, p. 1995 - 2000 (2007)
1-Deoxy-l-fructose, a very rare monosaccharide, was produced by hydrogenation of 6-deoxy-l-mannose (l-rhamnose)-the only cheaply available deoxy sugar-to 1-deoxy-l-mannitol (l-rhamnitol) followed by oxidation with Enterobacter aerogenes IK7. The entire procedure was conducted in water and shows the power of green environmentally friendly chemistry combined with biotechnology in the preparation of new monosaccharides with potential for novel bioactive properties or alternative foodstuffs; the reactions here are reported on a multigram scale but would be reproducible on a very large scale.
Efficient enzymatic synthesis of l-rhamnulose and l-fuculose
Wen, Liuqing,Zang, Lanlan,Huang, Kenneth,Li, Shanshan,Wang, Runling,Wang, Peng George
supporting information, p. 969 - 972 (2016/07/26)
l-Rhamnulose (6-deoxy-l-arabino-2-hexulose) and l-fuculose (6-deoxy-l-lyxo-2-hexulose) were prepared from l-rhamnose and l-fucose by a two-step strategy. In the first reaction step, isomerization of l-rhamnose to l-rhamnulose, or l-fucose to l-fuculose was combined with a targeted phosphorylation reaction catalyzed by l-rhamnulose kinase (RhaB). The by-products (ATP and ADP) were selectively removed by silver nitrate precipitation method. In the second step, the phosphate group was hydrolyzed to produce l-rhamnulose or l-fuculose with purity exceeding 99% in more than 80% yield (gram scale).
