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(2002), "Enzymatic synthesis of octyl glucoside by almond β ..

The compounds possessing antiproliferative activity, 10, 11, 12, 13, 15, 17, 19a and 19b, share common structural components that had been included in their design. To our surprise, the [13]-macro-dilactone unit was not essential for activity. All of the bioactive compounds contain a glucosyl unit and an octyl (C8) chain. Furthermore, the majority of these molecules contain an α-linkage between the glucose unit and the alkyl chain. However, the most promising compounds, as measured by either therapeutic index (compound 10) or IC50 (compound 13), contained the [13]-macro-dilactone. In the case of 10 in particular, the cytostatic and cytotoxic activities were clearly separable, with a wide concentration range for its subtoxic antiproliferative activity. Based on this and its micromolar IC50, it is likely that 10 does not act by merely having a nonspecific effect on cells, such as disrupting the integrity of cellular membranes. Instead, this compound may target some factor(s) involved in cell cycle progression. In summary, we have demonstrated the application of our published synthesis to access a novel class of antiproliferative agents.

The biological activities of a family of novel, lipid-linked 13-membered-ring macro-dilactones are reported. These [13]-macro-dilactones were synthesized by diacylation of functionalized diols, followed by ring-closing metathesis under conditions we had previously reported. Antimigratory, cytostatic and cytotoxic activities of the compounds against cancer cells were evaluated. Compound 13 was the most potent in the series, while compound 10 had the broadest concentration range of subtoxic antiproliferative activity. These compounds share common structural components, namely the [13]-macro-dilactone templated by an octyl α-glucoside 4,6-diol.

the synthesis of alkyl glucosides in ..
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Journal of Nanoscience and Nanotechnology

Structure of surfactant phases in water
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Almond beta-D-glucosidase was used to catalyze alkyl-beta-D-glucoside synthesis by reacting glucose and the alcohol in organic media. The influence of five different solvents and the thermodynamic water activity on the reaction have been studied. The best yields were obtained in 80 or 90% (v/v) tert-butanol, acetone, or acetonitrile where the enzyme is very stable. In this enzymatic synthesis under thermodynamic control, the yield increases as the water activity of the reaction medium decreases. Enzymatic preparative-scale syntheses were performed in a tert-butanol-water mixture which was found to be the most appropriate medium. 2-Hydroxybenzyl beta-D-glucopyranoside was obtained in 17% yield using a 90:10 (v/v) tert-butanol-water mixture. Octyl-beta-glucopyranoside was obtained in 8% yield using a 60:30:10 (v/v) tert-butanol-octanol-water mixture. (C) 1997 by Elsevier Science Inc.

UNSPECIFIED. (1997)Solvent effect on enzyme-catalyzed synthesis of beta-D-glucosides using the reverse hydrolysis method: Application to the preparative-scale synthesis of 2-hydroxybenzyl and octyl beta-D-glucopyranosides. ENZYME AND MICROBIAL TECHNOLOGY, 20 (8). pp. 597-603. ISSN 0141-0229

geraniol, 106-24-1 - The Good Scents Company

Almond beta-D-glucosidase was used to catalyze alkyl-beta-D-glucoside synthesis by reacting glucose and the alcohol in organic media. The influence of five different solvents and the thermodynamic water activity on the reaction have been studied. The best yields were obtained in 80 or 90% (v/v) tert-butanol, acetone, or acetonitrile where the enzyme is very stable. In this enzymatic synthesis under thermodynamic control, the yield increases as the water activity of the reaction medium decreases. Enzymatic preparative-scale syntheses were performed in a tert-butanol-water mixture which was found to be the most appropriate medium. 2-Hydroxybenzyl beta-D-glucopyranoside was obtained in 17% yield using a 90:10 (v/v) tert-butanol-water mixture. Octyl-beta-glucopyranoside was obtained in 8% yield using a 60:30:10 (v/v) tert-butanol-octanol-water mixture. (C) 1997 by Elsevier Science Inc.

The first garden strawberry was grown in Brittany, France during the late 18th century
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