42400-32-8Relevant academic research and scientific papers
C1 Oxidation/C2 Reduction Isomerization of Unprotected Aldoses Induced by Light/Ketone
Masuda, Yusuke,Tsuda, Hiromu,Murakami, Masahiro
, p. 2755 - 2759 (2020/01/25)
Unprotected aldoses in water undergo an isomerization reaction via a radical pathway when irradiated with light in the presence of water-soluble benzophenone. Whereas its anomeric carbon (C1) is oxidized to a carboxy group, the hydroxy group on the C2 carbon is replaced by hydrogen. The generated 2-deoxy lactones are readily reduced to the corresponding 2-deoxy aldoses, which are often contained in bioactive compounds.
A highly selective Bi(OTf)3 mediated fragmentation-contraction of δ-ortholactones. A facile route to functionalized γ-lactones
Baddeley, Kate L.,Cook, Matthew J.
, p. 5172 - 5182 (2018/06/04)
A very selective method for the formation of γ-lactones from pyranyl ortholactones has been developed which occurs via a fragmentation-acetate migration-ring contraction process. The reaction is very functional group tolerant, providing functionalized γ-l
A concise approach to the synthesis of all twelve 5-deoxyhexoses: d-tagatose-3-epimerase-a reagent that is both specific and general
Rao, Devendar,Best, Daniel,Yoshihara, Akihide,Gullapalli, Pushpakiran,Morimoto, Kenji,Wormald, Mark R.,Wilson, Francis X.,Izumori, Ken,Fleet, George W.J.
scheme or table, p. 3559 - 3563 (2009/10/26)
2-Deoxy-d-glucitol and 2-deoxy-d-allitol, both prepared as crystalline polyols from d-erythronolactone, are oxidized by Gluconobacter thailandicus NBRC 3254 to 5-deoxy-d-threo-hexulose [5-deoxy-d-fructose = 5-deoxy-l-sorbose] and 5-deoxy-d-erythro-hexulose [5-deoxy-l-psicose = 5-deoxy-d-tagatose], respectively. d-Tagatose-3-epimerase (DTE) equilibrates 5-deoxy-d-fructose to 5-deoxy-d-psicose and 5-deoxy-l-psicose to 5-deoxy-l-fructose, providing substrates for the preparation of all eight d- and l-5-deoxy aldohexoses by aldose isomerases. This combination of chemical and biotechnological methods allows a concise approach to the synthesis of all twelve 5-deoxy hexoses and further demonstrates the range of deoxy sugar substrates on which DTE is active. NMR studies show that 5-deoxy-d-fructose exists solely as the β-pyranose form whereas both pyranoses of 5-deoxy-d-fructose [α:β. 22:78] are observed. [For the sake of clarity, all ketoses in this Letter are shown in blue, alditols in red and aldoses in purple.].
Photoinduced electron-transfer α-deoxygenation of aldonolactones. Efficient synthesis of 2-deoxy-d-arabino-hexono-1,4-lactone
Bordoni, Andrea,de Lederkremer, Rosa M.,Marino, Carla
, p. 1788 - 1795 (2007/10/03)
A photoinduced electron-transfer (PET) reaction was used for the deoxygenation at C-2 of aldonolactones derivatized as 2-O-[3-(trifluoromethyl)benzoyl] or benzoyl esters. By irradiation of different d-galactono- and d-glucono-1,4-derivatives, with a 450 W
Rare keto-aldoses from enzymatic oxidation: Substrates and oxidation products of pyranose 2-oxidase
Freimund, Stefan,Huwig, Alexander,Giffhorn, Friedrich,Koepper, Sabine
, p. 2442 - 2455 (2007/10/03)
Pyranose oxidases are known to oxidise D-glucose, D-xylose and L- sorbose to keto-aldoses, biochemically interesting compounds that may also be used for synthetic purposes in a variety of reactions. In this study pyranose oxidase from the basidiomycete Peniophora gigantea was investigated, and it was found that this enzyme is able to oxidise a broad variety of substrates very effectively. In analogy to its natural mode of action, most substrates are oxidised regioselectively in position 2. Certain compounds, however, are converted into 3-keto derivatives, and the enzyme even exhibits transfer potential, that is, disscharides are formed from β-glycosides of higher alcohols. Substrates that may be oxidised at C-2 in yields between 40-98% are D-allose, D-galactose, 6-deoxy-D-glucose, D-gentiobiose, α-D-glucopyranosyl fluoride and the very interesting 3-deoxy-D-glucose. 1,5-Anhydro-D-glucitol (1-deoxy-D-glucose) is very effectively oxidised in position 2 in 98% yield and additionally gives a product of dioxidation at C-2 and C-3 upon prolonged reaction time Selective oxidation at C-3 was found for 2-deoxy-D-glucose in very good yields and for methyl β-D-gluco- and methyl β-galactopyranoside in lower yields. All oxidation products were unequivocally characterised by NMR spectroscopy and/or chemical derivatisation. In addition, the kinetic data of the enzymatic reactions were determined for all substrates. On the basis of these data and the structural characteristics of the substrates, a model for the minimal structural requirements of the enzyme-substrate interaction is suggested. The enzyme presumably uses two different binding modes for the regioselective C-2 and the C-3 oxidations, which are described.
