Deuterium isotope effects in a - pyranose and in pyranose-furanose interconversions

Isbell, Horace S.; Wade, Clarence W. R.

doi:10.6028/jres.071a.020

Cited by 16 publications

(1 citation statement)

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“…The anomeric 1‐OH group at the C1 carbon of glucose (Glc‐1) undergoes a known temperature‐ and pH‐dependent chemical exchange with unlabeled water in solution, which is provoked by the interconversion of the α and β forms of glucose (a process termed mutarotation). Thus, the apparent metabolic conversion rate of Glc‐1 glucose into H 2 17 O must be corrected for chemical exchange.…”

Section: Methodsmentioning

confidence: 99%

Initial investigation of glucose metabolism in mouse brain using enriched¹⁷O-glucose and dynamic¹⁷O-MRS

et al. 2017

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In this initial work, the in vivo degradation of O-labeled glucose was studied during cellular glycolysis. To monitor cellular glucose metabolism, direct O-magnetic resonance spectroscopy (MRS) was used in the mouse brain at 9.4 T. Non-localized spectra were acquired with a custom-built transmit/receive (Tx/Rx) two-turn surface coil and a free induction decay (FID) sequence with a short TR of 5.4 ms. The dynamics of labeled oxygen in the anomeric 1-OH and 6-CH OH groups was detected using a Hankel-Lanczos singular value decomposition (HLSVD) algorithm for water suppression. Time-resolved O-MRS (temporal resolution, 42/10.5 s) was performed in 10 anesthetized (1.25% isoflurane) mice after injection of a 2.2 M solution containing 2.5 mg/g body weight of differently labeled O-glucose dissolved in 0.9% physiological saline. From a pharmacokinetic model fit of the H O concentration-time course, a mean apparent cerebral metabolic rate of O-labeled glucose in mouse brain of CMR = 0.07 ± 0.02 μmol/g/min was extracted, which is of the same order of magnitude as a literature value of 0.26 ± 0.06 μmol/g/min reported by F-fluorodeoxyglucose ( F-FDG) positron emission tomography (PET). In addition, we studied the chemical exchange kinetics of aqueous solutions of O-labeled glucose at the C1 and C6 positions with dynamic O-MRS. In conclusion, the results of the exchange and in vivo experiments demonstrate that the C6- OH label in the 6-CH OH group is transformed only glycolytically by the enzyme enolase into the metabolic end-product H O, whereas C1- OH ends up in water via direct hydrolysis as well as glycolysis. Therefore, dynamic O-MRS of highly labeled O-glucose could provide a valuable non-radioactive alternative to FDG PET in order to investigate glucose metabolism.

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Section: Methodsmentioning

confidence: 99%

Initial investigation of glucose metabolism in mouse brain using enriched¹⁷O-glucose and dynamic¹⁷O-MRS

et al. 2017

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Thermodynamic and kinetic analysis of the dimerization of aqueous glyoxal

Fratzke

Reilly

1986

Int J of Chemical Kinetics

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Equilibria and rates of interconversion between monomeric and dimeric glyoxal were measured in aqueous solution. The equilibrium constant [G2]/[GJ2 was 0.56 M-' at 25"C, and was hardly affected by changes of ionic strength and pH but increased rapidly with increase of temperature. The rate of depolymerization was first-order in dimer, with the pseudo first-order rate coefficient in the pH range 1.

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Ionization and mutarotation of hexoses in aqueous alkaline solution as studied by ¹³C NMR spectroscopy

Wit

Kieboom

Bekkum

1979

Recl. Trav. Chim. Pays‐Bas

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355the nitrogen atom being in apical and the three carbon ligands in the equatorial positions. The lead atom lies slightly below the plane of the carbon ligands to the side of the iodine atom. The I-Pb-N bond angle of 168.8" is slightly smaller than the Br-Sn-N bond angle (171.00) in the chiral tin compound mentioned above. The Pb-N distance of 2.688 8, gives evidence of the intramolecular interaction of the lead atom with the nitrogen atom. The H(6)-I distance is 3.063 8, and the H(6)-Pb distance 3.227 8,. If in solution approximately the same structure is present the low-field shift of H(6) in the PMR spectrum may be caused by anisotropic deshielding by the Pb-I bonding electrons. Full details concerning the X-ray study will be published soon9.New synthetic routes to compounds of the types ArAr'Pb-(OAc), and ArRPb(OAc), are being developed. These routes are expected to enable the introduction of a large variety of aryl and alkyl groups and the possible detection of chirality in the resulting organolead compounds by spectroscopic means. Experimental partMelting points are uncorrected. The PMR spectra were recorded on a Jeol-PS 100 NMR spectrometer using tetramethylsilane (TMS) as internal standard. Ether was dried over sodium and distilled. (4-Methylphenyl) lead triaceta~e~ and (4-meihylphenyl) (4-methoxyphenyljlead diacetate4 were prepared by literature procedures (4-Methylphenyl) (4-methoxyphenyl) lead diiodide.This compound was prepared by the addition of 21.5 g (143 mmol) of Nal dissolved in 50 ml of acetone to 17.0 g (28.6 mmol) (4-CH3C,H,)-(4-CH,OC,H,)Pb(OAc), dissolved in 100 ml of chloroform at room temperature. After cooling at O°C NaOAc crystallized almost completely from the mixture. Subsequently the NaOAc was filtered off and the chloroform/acetone was partly removed under reduced pressure. Upon addition of 100 ml of ethanol and cooling at -I5OC bright yellow crystals precipitated. Yield 86%; m.p. 81.5-82.5OC.2-( Dimethylaminomethyl)phenyllithiwn was prepared by a literature procedure' (4-Methylphenyl) (4-methoxyphenyl)[Z-(dimethylaminomethyl)phenyl]leadiodide. 50 ml of the reaction mixture of 2-(dimethylaminomethyl)phenyllithium in ether/hexane, containing ca. 10 mmol of the aryllithium compound, was slowly added to a solution of 6.6 g (10 mmol) of (4-CH30C6H,)(4-CH,C,H~Pb12 in 100 ml of dry ether in a nitrogen atmosphere at -20°C. The mixture was allowed to warm up to room temperature and was stirred for 3 h. The reaction mixture was then hydrolyzed in 50 ml of ice/water containing 5 g of ammonium chloride, the ether layer was separated and dried over sodium sulfate, the ether was distilled off and the oily residue was taken up in 15 ml of chloroform. After addition of 25 ml of ethanol the triorganolead iodide slowly crystallized at -15OC. The pale yellow crystals were collected by filtration and dried in vacuo. Yield 1.8 g (27%); m.p. 155OC.This compound was prepared in a similar way starting with 6.0 g (10 mmol) of tris(4-methylpheny1)lead iodide. Yield 1.9 g (31 %); m.p. 127-128OC (dec.). ~~ H ....

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Deuterium isotope effects in a - pyranose and in pyranose-furanose interconversions

Cited by 16 publications

References 16 publications

Initial investigation of glucose metabolism in mouse brain using enriched¹⁷O-glucose and dynamic¹⁷O-MRS

Initial investigation of glucose metabolism in mouse brain using enriched¹⁷O-glucose and dynamic¹⁷O-MRS

Thermodynamic and kinetic analysis of the dimerization of aqueous glyoxal

Ionization and mutarotation of hexoses in aqueous alkaline solution as studied by ¹³C NMR spectroscopy

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Deuterium isotope effects in a - pyranose and in pyranose-furanose interconversions

Cited by 16 publications

References 16 publications

Initial investigation of glucose metabolism in mouse brain using enriched17O-glucose and dynamic17O-MRS

Initial investigation of glucose metabolism in mouse brain using enriched17O-glucose and dynamic17O-MRS

Thermodynamic and kinetic analysis of the dimerization of aqueous glyoxal

Ionization and mutarotation of hexoses in aqueous alkaline solution as studied by 13C NMR spectroscopy

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Initial investigation of glucose metabolism in mouse brain using enriched¹⁷O-glucose and dynamic¹⁷O-MRS

Initial investigation of glucose metabolism in mouse brain using enriched¹⁷O-glucose and dynamic¹⁷O-MRS

Ionization and mutarotation of hexoses in aqueous alkaline solution as studied by ¹³C NMR spectroscopy