Stereoselective synthesis of chirally deuterated (S)-d-(6-2H1)glucose

Xu, Lin; Price, Neil P. J.

doi:10.1016/j.carres.2004.02.010

Cited by 18 publications

(11 citation statements)

References 17 publications

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“…Synthesis of ( S )- d -6-deutero-glucose was already described by Xu 15 and used as a substrate for methyl 2,3,4-tri- O -benzyl- d -(6,6-2H 2 )glucopyranoside which upon Swern oxidation of 6-OH group and subsequent reduction of an aldehyde with nondeuterated ( R )-(+)-Alpine-Borane gave with high optical purity an ( S ) isomer. As there was no need in our studies for pure ( S ) or ( R ) stereoisomers; we opted for a rather simpler high yield synthesis of 6-deutero-glucose ( 19 ) as an ( S / R ) mixture, as shown in Scheme 4.…”

Section: Resultsmentioning

confidence: 99%

d-Glucose and d-mannose-based metabolic probes. Part 3: Synthesis of specifically deuterated d-glucose, d-mannose, and 2-deoxy-d-glucose

Fokt

Skóra

Conrad

et al. 2013

Carbohydrate Research

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Altered carbohydrate metabolism in cancer cells was first noted by Otto Warburg more than 80 years ago. Upregulation of genes controlling the glycolytic pathway under normoxia, known as the Warburg effect, clearly differentiates malignant from non-malignant cells. The resurgence of interest in cancer metabolism aims at a better understanding of the metabolic differences between malignant and non-malignant cells and the creation of novel therapeutic and diagnostic agents exploiting these differences. Modified d-glucose and d-mannose analogs were shown to interfere with the metabolism of their respective monosaccharide parent molecules and are potentially clinically useful anticancer and diagnostic agents. One such agent, 2-deoxy-d-glucose (2-DG), has been extensively studied in vitro and in vivo and also clinically evaluated. Studies clearly indicate that 2-DG has a pleiotropic mechanism of action. In addition to effectively inhibiting glycolysis, 2-DG has also been shown to affect protein glycosylation. In order to better understand its molecular mechanism of action, we have designed and synthesized deuterated molecular probes to study 2-DG interference with d-glucose and d-mannose metabolism using mass spectrometry. We present here the synthesis of all desired probes: 2-deutero-d-glucose, 2-deutero-d-mannose, 6-deutero-d-glucose, 6-deutero-d-mannose, and 2-deutero-2-deoxy-d-glucose as well as their complete chemical characterization.

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Section: Resultsmentioning

confidence: 99%

d-Glucose and d-mannose-based metabolic probes. Part 3: Synthesis of specifically deuterated d-glucose, d-mannose, and 2-deoxy-d-glucose

Fokt

Skóra

Conrad

et al. 2013

Carbohydrate Research

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“…of Tf 2 O at -60°C in the presence of the acid scavenger 2,4,6-tri-tert-butylpyrimidine (TTBP). [24] After 15 min, during which time the temperature gradually rose to -50°C, acceptor 11 [25] was added and then the reaction mixture was warmed to room temperature. Disaccharide 12 was isolated in 86 % yield as an anomeric mixture (α/β = 1:4).…”

Section: Resultsmentioning

confidence: 99%

Study of the Glycosidation Properties of 1‐Thiomannosazidopyranosides and 1‐Thiomannosaziduronic Acid Esters

et al. 2006

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A study of the glycosylation properties of 1‐thiomannosazides with a variety of electron‐withdrawing substituents in combination with the Ph2SO/Tf2O and NIS/TMSOTf reagent systems is presented. Further, assembly of the fully protected trisaccharide 26, which corresponds to the repeating unit of the enterobacterial common antigen, using both an orthogonal and a chemoselective coupling strategy and based on the outcome of our glycosylation studies, is discussed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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“…Saturated sodium bicarbonate (200 mL) was added, the organic layer removed, subsequently washed with saturated sodium bicarbonate, brine, and later dried over Na 2 SO 4 and filtered through Celite. The solvent was removed under reduced pressure and the resulting aldehyde was dissolved in 50 mL of THF and 2 H-AlpineBorane (18.3 mL, 60 mmol), prepared according to the Midland’s procedure 6. was added under atmosphere of nitrogen.…”

Section: Methodsmentioning

confidence: 99%

“…Therefore, a number of approaches have been used for the reduction of deuterated 5′-oxosugar derivatives by chiral hydride donors, including (−)-isobornyloxymagnesium bromide, 4 chloro(diisopinocampheyl)borane, 5 or AlpineBorane. 6 Alternatively, non-deuterated 5′-oxosugars were reduced with deuterated isobornyloxymagnesium bromide or deutero-AlpineBorane, 7 with the latter approach successfully utilized for preparation of 5′-deuterated ribonucleosides. 8 Since the preparation of deuterated AlpineBorane is straightforward following hydroboration of α-pinene with in situ generated deutero-borabicyclononane ( d -BBN), 7 we utilized this approach for our structural study of damaged DNA.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective Nucleoside Deuteration for NMR Studies of DNA

Lukin

Santos

2010

Nucleosides, Nucleotides and Nucleic Acids

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A procedure has been elaborated for stereoselective deuterium substitution of one of the diastereotopic 5′-protons in 2′-deoxynucleotides. The synthetic scheme uses the reduction of the 5-oxosugar derivative with deuterated Alpine-Borane. The resulting deuterosugar is converted into pyrimidine nucleosides and incorporated into DNA using standard protocols. Comparison of 2D NMR spectra of the fully protonated and partially deuterated duplexes allowed us to assign diastereotopic 5′ protons, increasing the number of experimental restraints used for structure determination.

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Stereoselective synthesis of chirally deuterated (S)-d-(6-2H1)glucose

Cited by 18 publications

References 17 publications

d-Glucose and d-mannose-based metabolic probes. Part 3: Synthesis of specifically deuterated d-glucose, d-mannose, and 2-deoxy-d-glucose

d-Glucose and d-mannose-based metabolic probes. Part 3: Synthesis of specifically deuterated d-glucose, d-mannose, and 2-deoxy-d-glucose

Study of the Glycosidation Properties of 1‐Thiomannosazidopyranosides and 1‐Thiomannosaziduronic Acid Esters

Stereoselective Nucleoside Deuteration for NMR Studies of DNA

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