154-58-5Relevant articles and documents
An efficient and selective conversion of sorbitol in ionic liquids: Use of ion exchange resin as a solid acid catalyst
Kamimura, Akio,Murata, Kengo,Kawamoto, Takuji
, p. 3616 - 3618 (2017)
Sorbitol was readily converted by heating in hydrophobic ionic liquids by the presence of ion exchange resins. Chemoseletivity of the dehydration depended on the choice of ion exchange resin; Nafion selectively produced isosorbide while Amberlite gave 1,5-anhydrosorbitol along with unreacted sorbitol. Ionic liquids used in the reaction were readily recovered by simple extraction procedure. With these procedures, we succeeded to prepare isosorbide in pure form, not contaminated with either ionic liquids or acid catalyst, by simple experimental procedure.
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.
Rapid conversion of sorbitol to isosorbide in hydrophobic ionic liquids under microwave irradiation
Kamimura, Akio,Murata, Kengo,Tanaka, Yoshiki,Okagawa, Tomoki,Matsumoto, Hiroshi,Kaiso, Kouji,Yoshimoto, Makoto
, p. 3257 - 3259 (2014)
Sorbitol was effectively converted to isosorbide by treatment with [TMPA][NTf2] in the presence of catalytic amounts of TsOH under microwave heating at 180°C. The reaction completed within 10 min and isosorbide was isolated to about 60%. Ionic liquids were readily recovered by an extraction treatment and reused several times.
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.
The kinetics of the spontaneous, proton- and AlIII-catalysed hydrolysis of 1,5-anhydrocellobiitol - Models for cellulose depolymerization in paper aging and alkaline pulping, and a benchmark for cellulase efficiency
Baty, John William,Sinnott, Michael L.
, p. 1516 - 1524 (2005)
The kinetics of the spontaneous, proton- and AlIII-catalysed hydrolyses of the Cl-O4′ bond in 1,5-anhydrocellobiitol have been measured at elevated temperatures (125.0-220.0°C). Data for the first two processes extrapolate to the expression k = (8.6 ± 2.1 × 10-16) + (1.4 ± 0.2 × 109-pH) s-1 at 25°C. These room-temperature figures were used to model cellulose depolymerization by the af Ekenstam equation. The spontaneous process is too slow to contribute to loss of paper strength on aging, and even the acid-catalysed process is significant only below -pH 4.0. However, the spontaneous hydrolysis readily accounts for the reduction of cellulose degree of polymerization (DP) during alkaline (e.g., kraft) pulping of cellulose fibres. Efficient electrophilic catalysis by Al III was observed at 150.0°C in 0.1 mol/L succinate buffers of room temperature pH 3.05 and 3.35 (k2 = 8.1 ± 0.4 ± 10-3 and 4.2 ± 0.2 × 10-3 (mol/L) -1 s-1, respectively). The apparent activation energy of the AlIII-catalysed process was 31 ± 4 kJ mol-1, lower than that of the proton-catalysed path, suggesting the electrophilic catalysis increases in importance as the temperature approaches ambient. Consequently, it appears that the culprit in the impermanence of "rosin-alum"-sized paper is AlII, directly acting as a Lewis acid, not the AlIII hydration sphere as a Bronsted acid. Conservation measures should either address this or be generic (e.g., low-temperature storage).
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.
First protection-free protocol for synthesis of 1-deoxy sugars through glycosyl dithiocarbamate intermediates
Li, Gefei,Noguchi, Masato,Nakamura, Kensuke,Hayasaka, Ryohei,Tanaka, Yuuki,Shoda, Shin-ichiro
, p. 3428 - 3431 (2018)
A practical two-step synthetic process for 1-deoxy sugars has been established. The process consists of the direct introduction of a dimethyldithiocarbamate group into the anomeric center of unprotected sugars and subsequent hydrogenation in the AIBN-H3PO2-NaHCO3 system. No protecting groups are needed to synthesize 1-deoxy monosaccharides and 1-deoxy disaccharides.
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.
Maplexins, new α-glucosidase inhibitors from red maple (Acer rubrum) stems
Wan, Chunpeng,Yuan, Tao,Li, Liya,Kandhi, Vamsikrishna,Cech, Nadja B.,Xie, Mingyong,Seeram, Navindra P.
, p. 597 - 600 (2012)
Thirteen gallic acid derivatives including five new gallotannins, named maplexins A-E, were isolated from red maple (Acer rubrum) stems. The compounds were identified by spectral analyses. The maplexins varied in number and location of galloyl groups attached to 1,5-anhydro-d-glucitol. The isolates were evaluated for α-glucosidase inhibitory and antioxidant activities. Maplexin E, the first compound identified with three galloyl groups linked to three different positions of 1,5-anhydro-d-glucitol, was 20 fold more potent than the α-glucosidase inhibitory drug, Acarbose (IC50 = 8 vs 160 μM). Structure-activity related studies suggested that both number and position of galloyls attached to 1,5-anhydro-d-glucitol were important for α-glucosidase inhibition.
