An alternative synthesis of 4-deoxy-4-fluoro-d-glucose and its transport in the human erythrocyte

Lopes, Diago Philip.; Taylor, Norman

doi:10.1016/s0008-6215(00)85481-6

Cited by 19 publications

(2 citation statements)

References 19 publications

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“…Sanofi-Aventis also developed and explored the biological potential of the 4-deoxy-4-fluoroglucopyranose candidate since it is a part of a sodium–glucose transporter inhibitor SAR7226 . In addition, analogues of 4-fluoroglucopyranose were evaluated as efficient transporters in human erythrocytes and in biochemical investigations . These successful applications clearly indicated that this class of carbohydrates could be considered as a valuable biological tool and opened the doors to the investigation of polyfluorinated glucopyranose analogues.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Lipophilicity of Trifluorinated Analogues of Glucose

et al. 2019

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In this work, we have developed synthetic routes for novel trifluorinated glucopyranose analogues using a Chiron approach. This strategy used inexpensive levoglucosan as a starting material, and we achieved a microwave glycosylation method as a key step. All analogues adopted standard 4 C 1 glucopyranose conformations, and a gauche−gauche conformation for the fluoromethyl group (C5−C6 linkage) was ascertained for congeners with a fluorine atom at C-6. Finally, the lipophilicity of trifluorinated glucose analogues was assessed with a log P determination method based on 19 F NMR spectroscopy.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Lipophilicity of Trifluorinated Analogues of Glucose

et al. 2019

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“…In such applications, the fluorine nucleus serves the multiple purposes of allowing observation of intraand extracellular FDG pools as well as retarding the metabolism of the fluorinated compounds so that relatively long-term NMR studies can be carried out. However, the substitution of the fluorine nucleus for a hydroxyl group also alters the interaction of the glucose with both solvent and transporter, and this can serve to test various hypotheses regarding the glucose-transporter interaction (Barnett et al, 1973;Riley & Taylor, 1973;Lopes & Taylor, 1979). In addition to questions regarding transport mechanism, characterization of the transport behavior of fluorinated glucose analogs is important in view of their use in PET scanning (Tewson et al, 1978;Vyska et al, 1985).…”

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Anomeric Dependence of Fluorodeoxyglucose Transport in Human Erythrocytes

O’Connell¹,

Gabel²,

London³

1994

Biochemistry

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The transport of several n-fluoro-n-deoxy-D-glucose derivatives across the human erythrocyte membrane has been studied under equilibrium exchange conditions using one- and two-dimensional nuclear magnetic resonance (NMR) techniques. This approach is based on the intracellular 19F shift, which was found to depend on the anomeric form and on the F/OH substitution position. Since the transport behavior of both glucose anomers can be followed simultaneously, this approach is particularly sensitive to differences in anomeric permeability. For 2-, 3-, 4-, and 6-fluorodeoxyglucose analogs, the alpha anomers permeate more rapidly, and the P alpha/P beta ratio is dependent on the position of fluorination, with values of 1.1, 1.3, 2.5, and 1.6, respectively, obtained at 37 degrees C. These results have been analyzed in terms of a simple alternating conformation model for the glucose transporter. Although mutarotase activity has been reported for red cells, mutarotation behavior for all anomers was found to be completely negligible on the transport and spin-lattice relaxation time scales. Metabolic transformation of the fluorinated glucose analogs, primarily to fluorinated gluconate and sorbitol analogs, is very slow and does not significantly interfere with the transport measurements. A mean ratio of 2.6 was found for the extracellular/intracellular fluorine spin-lattice relaxation rates.

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Synthesis of 2‐deoxy sugars

Giese¹,

Gilges²,

Gröninger³

et al. 1988

Liebigs Ann. Chem.

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The reduction of acetylated or benzoylated glycosyl halides or selcnides with low concentrations of lribulylstannane leads to 2-dcoxy sugars. An important step in this radicalchain reaction is the cis-selective migration or an ester group. The broad applicability of this method is demonstrated by thc synthesis of mono-and dideoxy sugars, or PI-and Pdeoxy sugars, of dcoxypyranoses and deoxyiuranoses, of dcoxypentosyl-and -hexosyl carbohydrates.

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An alternative synthesis of 4-deoxy-4-fluoro-d-glucose and its transport in the human erythrocyte

Cited by 19 publications

References 19 publications

Synthesis and Lipophilicity of Trifluorinated Analogues of Glucose

Synthesis and Lipophilicity of Trifluorinated Analogues of Glucose

Anomeric Dependence of Fluorodeoxyglucose Transport in Human Erythrocytes

Synthesis of 2‐deoxy sugars

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