- d-Fructose Modification Enhanced Internalization of Mixed Micelles in Breast Cancer Cells via GLUT5 Transporters
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d-Fructose modified poly(ε-caprolactone)-polyethylene glycol (PCL-PEG-Fru) diblock amphiphile is synthesized via Cu(I)-catalyzed click chemistry, which self-assembles with D-α-tocopheryl polyethylene glycol 1000 succinate (TPGS) into PCL-PEG-Fru/TPGS mixed micelles (PPF MM). It has been proven that glucose transporter (GLUT)5 is overexpressed in MCF-7 cells other than L929 cells. In this study, PPF MM exhibit a significantly higher uptake efficiency than fructose-free PCL-PEG-N3/TPGS mixed micelles in both 2D MCF-7 cells and 3D tumor spheroids. Also, the presence of free d-fructose competitively inhibits the internalization of PPF MM in MCF-7 cells other than L929 cells. PPF MM show selective tumor accumulation in MCF-7 breast tumor bearing mice xenografts. Taken together, PPF MM represent a promising nanoscale carrier system to achieve GLUT5-mediated cell specific delivery in cancer therapy. (Figure presented.).
- Zhou, Xu,Qin, Xianyan,Gong, Tao,Zhang, Zhi-Rong,Fu, Yao
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- A mild acetolysis procedure for the regioselective removal of isopropylidene in di-O-isopropylidene-protected pyranoside systems
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A mild acetolysis method for the regioselective removal of isopropylidene group from di-O-isopropylidene-protected hexopyranosides is reported. O-Isopropylidene-protected intermediates play an important role in carbohydrate chemistry, as they are often found in commercially available furanosyl and pyranosyl materials, and some of them contain more than one O-isopropylidene groups. Methods that permit regioselective removal of O-isopropylidene groups are extremely valuable, as the number of steps in the total synthesis of complex oligosaccharides could be significantly decreased. Here we report that trifluoroacetic acid (TFA)/acetic anhydride (Ac2O) can be used to regioselectively convert one of the two O-isopropylidene groups to vicinal di-O-acetates in the di-O-isopropylidene-protected galacto- and fructo-pyranosyl systems, and the reagent is compatible with some common functionalities such as sulfonate esters, bromide, azide etc.
- Zhang, Pengfei,Ling, Chang-Chun
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- Concise synthesis of chiral N -Benzyl-α,α-Diarylprolinols through shi asymmetric epoxidation
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A concise and practical synthesis of chiral N-benzyl-α,α- diaryl-2-prolinols was developed through Shi asymmetric epoxidation, followed by double nucleophilic substitution of bromo-containing olefins. A series of enantioenriched N-benzyl-α,α-diaryl-2-prolinols were obtained with excellent enantioselectivities (96% ee) in moderate to good yields (40-76% yield). For the first time, enantiopure N-benzyl-α,α-diphenyl-2- prolinol was obtained from bromo-containing olefin using this methodology. Georg Thieme Verlag Stuttgart, New York.
- Li, Jie,Zhou, Hai,Weng, Jiangsen,Wang, Mingwen,Ge, Chengsheng,Tu, Wujie
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supporting information
p. 805 - 808
(2014/04/03)
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- An epoxidation approach to a chiral lactone: Application of the Shi epoxidation
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The large-scale epoxidation of the alkene 7 with the organo-catalyst, Epoxone (10), and Oxone as the oxidant is described. This is the first large-scale application of the Shi epoxidation methodology. The large-scale preparation of the catalyst 10 is also described. The potassium salt of the unsaturated acid precursor 7 was prepared by a Suzuki coupling from 3-fluorobenzyl chloride and the vinylborane 8 derived from 4-pentynoic acid.
- Ager, David J.,Anderson, Ken,Oblinger, Eric,Shi, Yian,Vanderroest, James
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- Acetalation studies. Part IX. Reaction of sucrose and some related sugars with acetone in the presence of iodine; a novel cleavage-isopropylidenation method
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An efficient cleavage-isopropylidenation reaction of sucrose, catalyzed by iodine, is described.Related D-fructofuranosyl-containing oligosaccharides and their individual monosaccharide units were treated in a similar manner to yield isopropylidenated monosaccharide derivatives.The reaction conditions are particularly mild and selective.Some mechanistic aspects of the procedure are also discussed.
- Verhart, Cor G. J.,Caris, Brigitte M. G.,Zwanenburg, Binne,Chittenden, Gordon J. F.
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p. 348 - 352
(2007/10/02)
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- Synthesis of Polymerizable Hexose Derivatives
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Polymerizable esters of methacrylic and acrylic acid with di-O-isopropylidenehexoses as alcohol components have been synthesized.
- Kossmehl, Gerhard,Volkheimer, Juergen
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p. 1127 - 1130
(2007/10/02)
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- GAS CHROMATOGRAPHY-MASS SPECTROMETRY OF HEXULOSES AND PENTULOSES AS THEIR O-ISOPROPYLIDENE DERIVATIVES: ANALYSIS OF PRODUCT MIXTURES FROM TRIOSE ALDOL-CONDENSATIONS
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Identification and quantitation of hexuloses and pentuloses in mixtures has been achived by gas chromatography-mass spectrometry of their O-isopropylidene derivatives.The method has been applied to product mixtures from triose aldol-condensations.The use of strongly basic anion-exchange resins as catalysts in the aldol condensation gives considerably higher proportions of fructose than when alkali or alkaline-earth hydroxides are applied.
- Morgenlie, Svein
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p. 215 - 222
(2007/10/02)
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