154-58-5Relevant articles and documents
Reductive Cleavage of Glycosides
Rolf, David,Gray, Gary R.
, p. 3539 - 3541 (1982)
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Honda,S. et al.
, p. 61 - 70 (1979)
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Design and synthesis of boron containing monosaccharides by the hydroboration of D-glucal for use in boron neutron capture therapy (BNCT)
Itoh, Taiki,Tamura, Kei,Ueda, Hiroki,Tanaka, Tomohiro,Sato, Kyouhei,Kuroda, Reiko,Aoki, Shin
, p. 5922 - 5933 (2018)
Boron neutron capture therapy (BNCT) is one of the radiotherapies that involves the use of boron-containing compounds for the treatment of cancer. Boron-10 (10B) containing compounds that can accumulate in tumor tissue are expected to be suitable agents for BNCT. We report herein on the design and synthesis of some new BNCT agents based on a D-glucose scaffold, since glycoconjugation has been recognized as a useful strategy for the specific targeting of tumors. To introduce a boryl group into a D-glucose scaffold, we focused on the hydroboration of D-glucal derivatives, which have a double bond between the C1 and C2 positions. It was hypothesized that a C–B bond could be introduced at the C2 position of D-glucose by the hydroboration of D-glucal derivatives and that the products could be stabilized by conversion to the corresponding boronic acid ester. To test this hypothesis, we prepared some 2-boryl-1,2-dideoxy-D-glucose derivatives as boron carriers and evaluated their cytotoxicity and cellular uptake activity to cancer cells, especially under hypoxic conditions.
New maplexins F-I and phenolic glycosides from red maple (Acer rubrum) bark
Yuan, Tao,Wan, Chunpeng,Liu, Ke,Seeram, Navindra P.
, p. 959 - 964 (2012)
Four new gallotannins, maplexins F-I (1-4), two new phenolic glycosides, rubrumosides A-B (5,6), and eleven known compounds were isolated from red maple (Acer rubrum) bark. Their structures were elucidated based on spectroscopic analysis. The maplexins contained three galloylated derivatives attached to different positions of 1,5-anhydro-glucitol and were 10-20 fold more potent α-glucosidase inhibitors than the clinical drug, Acarbose (IC 50=7-16 vs 161 μM), in vitro. These results support previous data suggesting that gallotannins are the main contributors to the α-glucosidase inhibitory activities of maple plant part extracts and that three substituents on the 1,5-anhydro-glucitol moiety are important for activity.
Mouse AKR1E1 is an ortholog of pig liver NADPH dependent 1,5-anhydro-D-fructose reductase
Sakuma, Motoki,Kubota, Shunichiro
, p. 872 - 876 (2008)
In many organisms, glycogen gives rise to 1,5-anhydro-D-fructose (AF), which is reduced to 1,5-anhydro-D-glucitol (AG). AF reductase, which catalyzes the latter reaction, was purified from pig liver, but mouse ortholog has not yet been reported. In the database, aldo-keto reductase family 1, member E1 (AKR1E1) showed highest homology to pig enzyme. We confirmed that cloned AKR1E1 is mouse ortholog based on enzymatic properties of purified recombinant protein.
An efficient method for the preparation of 1,5-anhydroalditol from unprotected carbohydrates via glycopyranosyl iodide
Uchiyama, Taketo,Shishikura, Keisuke,Ogawa, Koji,Ohshima, Yuuki,Miyairi, Shinichi
, p. 5294 - 5296 (2016)
A practical, facile method was developed for the preparation of 1,5-anhydroalditol via per-O-TMS-glycopyranosyl iodide with LiBH4. A series of 1,5-anhydroalditols were prepared in excellent yields (up to 92%) from unprotected carbohydrates within 2 days under mild conditions. In addition, multi-gram scale preparation of 1,5-anhydroglucitol (1,5-AG), a major polyol present in human serum, was developed using the same procedure without the need for chromatographic purification.
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Ness et al.
, p. 4547 (1950)
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EFFECTS OF IRON, COPPER, AND CHROMATE IONS ON THE OXIDATIVE DEGRADATION OF CELLULOSE MODEL COMPOUNDS
Blattner, Regine,Ferrier, Robert J.
, p. 73 - 82 (1985)
Iron(II) and iron(III) ions promote the degradation of the cellulose model 1,5-anhydrocellobiitol by oxygen and hydrogen peroxide; copper and chromate ions have marked and different effects on the iron catalysis.With starch, iron promotes the hydrogen peroxide-induced reaction and copper and chromate ions further enhance the reaction rate.The tensile strenght of paper board is reduced by the action of hydrogen peroxide and iron(II) salts, and mixtures of copper, chromate, and arsenate salts (CCA; a timber preservative) also promote degradation in the presence or absence of iron ions.The oxidation of 1,5-anhydrocellobiitol by oxygen in the presence of iron ions is strongly inhibited by CCA and by cetyltrimethylammonium chloride, and is accelerated by phenols and related compounds.
A protecting group-free approach for synthesizingC-glycosides through glycosyl dithiocarbamates
Li, Gefei,Noguchi, Masato,Arisaka, Genki,Tanaka, Yuuki,Shoda, Shin-Ichiro
supporting information, p. 3134 - 3138 (2021/04/21)
The first protection/deprotection-free process for radicalC-glycosylation has been achieved through one-step preparable glycosyl dithiocarbamates (GDTCs). The Giese-type reaction and radical allylation of unprotected GDTCs were successfully performed to obtain the corresponding α-C-glycosides stereoselectively under mild reaction conditions.
Modulating Electrostatic Interactions in Ion Pair Intermediates To Alter Site Selectivity in the C?O Deoxygenation of Sugars
Bowers, Bekah E.,Gagné, Michel R.,Lowe, Jared M.,Seo, Youngran
supporting information, p. 17297 - 17300 (2020/07/30)
Controlling which products one can access from the predefined biomass-derived sugars is challenging. Changing from CH2Cl2 to the greener alternative toluene alters which C?O bonds in a sugar are cleaved by the tris(pentafluorophenyl)borane/HSiR3 catalyst system. This increases the diversity of high-value products that can be obtained through one-step, high-yielding, catalytic transformations of the mono-, di-, and oligosaccharides. Computational methods helped identify this non-intuitive outcome in low dielectric solvents to non-isotropic electrostatic enhancements in the key ion pair intermediates, which influence the reaction coordinate in the reactivity-/selectivity-determining step. Molecular-level models for these effects have far-reaching consequences in stereoselective ion pair catalysis.
Harnessing the reactivity of poly(methylhydrosiloxane) for the reduction and cyclization of biomass to high-value products
Hein, Nicholas M.,Seo, Youngran,Lee, Stephen J.,Gagné, Michel R.
, p. 2662 - 2669 (2019/06/13)
Poly(methylhydrosiloxane) (PMHS) has been examined for its ability to reduce and subsequently cyclize carbohydrate substrates using catalytic tris(pentafluorophenyl)borane (BCF). The work herein is the first reported example of the direct conversion of monosaccharides to 1,4-anhydro and 2,5-anhydro products utilizing a hydrosiloxane reducing agent. PMHS is produced from waste products of the silicone industry, making it a green alternative to traditional hydrosilane reducing agents. This work thus contributes to the goal of utilizing renewable feedstocks in the production of fine-chemicals.
