Ensuiko Sugar Refining Co.

Tokyo, Japan

Ensuiko Sugar Refining Co.

Tokyo, Japan

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PubMed | Okayama University of Science, Ensuiko Sugar Refining Co., U.S. National Cancer Institute, Kurashiki University of Science and the Arts and Okayama University
Type: Journal Article | Journal: PloS one | Year: 2014

Although the encapsulation of paclitaxel into liposomes has been extensively studied, its significant hydrophobic and uncharged character has generated substantial difficulties concerning its efficient encapsulation into the inner water core of liposomes. We found that a more hydrophilic paclitaxel molecule, 7-glucosyloxyacetylpaclitaxel, retained tubulin polymerization stabilization activity. The hydrophilic nature of 7-glucosyloxyacetylpaclitaxel allowed its efficient encapsulation into the inner water core of liposomes, which was successfully accomplished using a remote loading method with a solubility gradient between 40% ethylene glycol and Cremophor EL/ethanol in PBS. Trastuzumab was then conjugated onto the surface of liposomes as immunoliposomes to selectively target human epidermal growth factor receptor-2 (HER2)-overexpressing cancer cells. In vitro cytotoxicity assays revealed that the immunoliposomes enhanced the toxicity of 7-glucosyloxyacetylpaclitaxel in HER2-overexpressing cancer cells and showed more rapid suppression of cell growth. The immunoliposomes strongly inhibited the tumor growth of HT-29 cells xenografted in nude mice. Notably, mice survived when treated with the immunoliposomes formulation, even when administered at a lethal dose of 7-glucosyloxyacetylpaclitaxel in vivo. This data successfully demonstrates immunoliposomes as a promising candidate for the efficient delivery of paclitaxel glycoside.


Patent
Ensuiko Sugar Refining Co. and Osaka Municipal Technical Research Institute | Date: 2013-06-03

The present invention provides a D-glucaric acid-producing bacterium and a method for producing D-glucaric acid. The present invention is characterized in that D-glucaric acid or a salt thereof is produced from one or more saccharides selected from the group consisting of D-glucose, D-gluconic acid and D-glucuronic acid with catalytic action of a specific alcohol dehydrogenase PQQ-ADH (1) and a specific aldehyde dehydrogenase PQQ-ALDH (2), and that D-glucaric acid or a salt thereof is produced by using a microorganism having the PQQ-ADH (1) and the PQQ-ALDH (2) or a processed product thereof in the presence of the one or more saccharides. The present invention can provide a microorganism having improved productivity of D-glucaric acid to be used for production of D-glucaric acid and a method for efficiently producing D-glucaric acid.


Wu Y.,University of Tokyo | Enomoto-Rogers Y.,University of Tokyo | Masaki H.,Ensuiko Sugar Refining Co. | Iwata T.,University of Tokyo
ACS Sustainable Chemistry and Engineering | Year: 2016

d-Glucaric acid (GA), an aldaric acid isolated from various vegetables and fruits, is an important biobased building block. Glucaric acid acetate (GAA), which is acyclic, was synthesized in an acetic anhydride/sulfuric acid mixture. GAA was converted to glucaric acid chloride acetate (GACA) and then polymerized with various diols and diamines in dimethylacetamide solution or by interfacial polymerization in water and chloroform solutions. The polyesters and polyamides were amphiphilic and soluble in water and common organic solvents. The weight-average molecular weights of the polyesters were (0.4-0.7) × 103 those of the polyamides obtained by solution and interfacial polymerizations were (5.9-8.0) × 103 and (14.5-20.8) × 103, respectively. Differential scanning calorimetry showed that the polyamides were thermoplastic and melted at ca. 140 °C, indicating crystallinity; the melting points increased with increasing number of diamine alkyl carbons. Novel biobased crystalline amphiphilic polymers were synthesized from GA. © 2016 American Chemical Society.


Enomoto-Rogers Y.,University of Tokyo | Masaki H.,Ensuiko Sugar Refining Co. | Ito T.,Ensuiko Sugar Refining Co. | Furihata K.,Tokyo University of Science | Iwata T.,University of Tokyo
Magnetic Resonance in Chemistry | Year: 2016

d-Glucaric acid (GA) is an aldaric acid and consists of an asymmetric acyclic sugar backbone with a carboxyl group positioned at either end of its structure (i.e., the C1 and C6 positions). The purpose of this study was to conduct a conformation analysis of flexible GA as a solution in deuterium oxide by NMR spectroscopy, based on J-resolved conformation analysis using proton–proton (3JHH) and proton–carbon (2JCH and 3JCH) coupling constants, as well as nuclear overhauser effect spectroscopy (NOESY). The 2JCH and 3JCH coupling constants were measured using the J-resolved heteronuclear multiple bond correlation (HMBC) NMR technique. NOESY correlation experiments indicated that H2 and H5 were in close proximity, despite the fact that these protons were separated by too large distance in the fully extended form of the chain structure to provide a NOESY correlation. The validities of the three possible conformers along the three different bonds (i.e., C2C3, C3C4, and C4C5) were evaluated sequentially based on the J-coupling values and the NOESY correlations. The results of these analyses suggested that there were three dominant conformers of GA, including conformer 1, which was H2H3:gauche, H3H4:anti, and H4H5:gauche; conformer 2, which was H2H3:gauche, H3H4:anti, and H4H5:anti; and conformer 3, which was H2H3:gauche, H3H4: gauche, and H4H5:anti. These results also suggested that all three of these conformers exist in equilibrium with each other. Lastly, the results of the current study suggested that the conformational structures of GA in solution were ‘bent’ rather than being fully extended. Copyright © 2016 John Wiley & Sons, Ltd. Copyright © 2016 John Wiley & Sons, Ltd.


Tonozuka T.,Tokyo University of Agriculture and Technology | Tamaki A.,Tokyo University of Agriculture and Technology | Yokoi G.,Tokyo University of Agriculture and Technology | Miyazaki T.,Tokyo University of Agriculture and Technology | And 8 more authors.
Enzyme and Microbial Technology | Year: 2012

Arthrobacter sp. K-1 β-fructofuranosidase (ArFFase), a glycoside hydrolase family 68 enzyme, catalyzes the hydrolysis and transfructosylation of sucrose. ArFFase is useful for producing a sweetener, lactosucrose (4G-β-d-galactosylsucrose). The primary structure of ArFFase is homologous to those of levansucrases, although ArFFase catalyzes mostly hydrolysis when incubated with sucrose alone, even at high concentration. Here, we determined the crystal structure of ArFFase in unliganded form and complexed with fructose. ArFFase consisted of a five-bladed β-propeller fold as observed in levansucrases. The structure of ArFFase was most similar to that of Gluconacetobacter diazotrophicus levansucrase (GdLev). The structure of the catalytic cleft of ArFFase was also highly homologous to that of GdLev. However, two amino acid residues, Tyr232 and Pro442 in ArFFase, were not conserved between them. A tunnel observed at the bottom of the catalytic cleft of ArFFase may serve as a water drain or its reservoir. © 2012 Elsevier Inc.


Ohta Y.,Japan Agency for Marine - Earth Science and Technology | Hatada Y.,Japan Agency for Marine - Earth Science and Technology | Hidaka Y.,Japan Agency for Marine - Earth Science and Technology | Shimane Y.,Japan Agency for Marine - Earth Science and Technology | And 9 more authors.
Applied Microbiology and Biotechnology | Year: 2014

A β-fructofuranosidase from Microbacterium saccharophilum K-1 (formerly known as Arthrobacter sp. K-1) is useful for producing the sweetener lactosucrose (4G-β-D-galactosylsucrose). Thermostability of the β-fructofuranosidase was enhanced by random mutagenesis and saturation mutagenesis. Clones with enhanced thermostability included mutations at residues Thr47, Ser200, Phe447, Phe470, and Pro500. In the highest stability mutant, T47S/S200T/F447P/F470Y/P500S, the half-life at 60°C was 182 min, 16.5-fold longer than the wild-type enzyme. A comparison of the crystal structures of the full-length wild-type enzyme and three mutants showed that various mechanisms appear to be involved in thermostability enhancement. In particular, the replacement of Phe447 with Val or Pro induced a conformational change in an adjacent residue His477, which results in the formation of a new hydrogen bond in the enzyme. Although the thermostabilization mechanisms of the five residue mutations were explicable on the basis of the crystal structures, it appears to be difficult to predict which amino acid residues should be modified to obtain thermostabilized enzymes. © 2014 Springer-Verlag.


Patent
Ensuiko Sugar Refining Co. and Okayama University | Date: 2013-03-22

In order to reduce the side effects of paclitaxel derivatives having excellent anti-cancer effects, an attempt was made to produce a liposome encapsulating paclitaxel derivatives such as paclitaxel monoglycosides and docetaxel monoglycosides. However, the introduction efficiency of paclitaxel derivatives, etc., into a liposome was poor, and this technique was not developed to a practical level. The present invention provides a method for producing a liposome encapsulating a paclitaxel monoglycoside and/or a docetaxel monoglycoside, and having an antibody specifically recognizing a cancer cell, the method comprising a step of bringing a liposome encapsulating a polyoxyethylene ester derivative, a lower alcohol, and a buffer or water into contact with a solution in which a paclitaxel monoglycoside and/or a docetaxel monoglycoside is dissolved in an alkylene glycol-containing buffer or water.


Patent
Ensuiko Sugar Refining Co. and Okayama University | Date: 2013-03-22

In order to reduce the side effects of paclitaxel derivatives having excellent anti-cancer effects, an attempt was made to produce a liposome encapsulating paclitaxel derivatives such as paclitaxel monoglycosides and docetaxel monoglycosides. However, the introduction efficiency of paclitaxel derivatives, etc., into a liposome was poor, and this technique was not developed to a practical level. The present invention provides a method for producing a liposome encapsulating a paclitaxel monoglycoside and/or a docetaxel monoglycoside, and having an antibody specifically recognizing a cancer cell, the method comprising a step of bringing a liposome encapsulating a polyoxyethylene ester derivative, a lower alcohol, and a buffer or water into contact with a solution in which a paclitaxel monoglycoside and/or a docetaxel monoglycoside is dissolved in an alkylene glycol-containing buffer or water.


Ohta Y.,Japan Agency for Marine - Earth Science and Technology | Ito T.,Ensuiko Sugar Refining Co. | Mori K.,Japan Agency for Marine - Earth Science and Technology | Nishi S.,Japan Agency for Marine - Earth Science and Technology | And 3 more authors.
International Journal of Systematic and Evolutionary Microbiology | Year: 2013

A Gram-stain-positive, non-motile, non-spore-forming, rod-shaped bacterium, designated strain K-1T, was isolated from soil at a sucrose refinery in Japan. The strain grew at 9-37 °C (optimum, 30 °C) and at pH 6-11 (optimum, pH 7.0). Phylogenetic analysis based on the full-length 16S rRNA gene sequence of strain K-1T revealed that it was a member of the genus Microbacterium. High 16S rRNA gene sequence similarities were found between strains K-1T and both Microbacterium pumilum NBRC 101279T (99.7 %) and Microbacterium deminutum NRRL B-24453T (99.5 %). However, the DNA-DNA hybridization values between strain K-1T and M. pumilum NBRC 101279T and M. deminutum NRRL B-24453T were only 12% and 10 %, respectively. The DNA G+C content of strain K-1T was 73 mol%. The major fatty acids of strain K-1T were anteiso-C15: 0 and anteiso-C17: 0, and the major menaquinones were MK-12 and MK- 13. The diamino acid in the cell-wall peptidoglycan was lysine. On the basis of these results, strain K-1T is considered to represent a novel species of the genus Microbacterium, for which the name Microbacterium saccharophilum sp. nov. is proposed. The type strain is K-1T (=NBRC 108778T=NCIMB 14782T). © 2013 IUMS.

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