Some Xanthate Methyl Esters of Glucose

Sanyal, Amiya K.; Purves, C. B.

doi:10.1139/v56-061

Cited by 10 publications

(3 citation statements)

References 14 publications

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“…Bovine pancreatic RNase A was obtained from Worthington Biochemical (Freehold, NJ). (26). 1,2;5,6-Di-O-isopropylidene-R-D-glucofuranose (2; 5.20 g, 20.0 mmol) (27) was dissolved in THF (100 mL), imidazole (30 mg) was added, and then NaH (1.0 g, 40 mmol) was added batchwise.…”

Section: Methodsmentioning

confidence: 99%

Pyridoxamine Protects Proteins from Functional Damage by 3-Deoxyglucosone: Mechanism of Action of Pyridoxamine

et al. 2007

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Pyridoxamine (PM) is a promising drug candidate for treatment of diabetic nephropathy. The therapeutic effect of PM has been demonstrated in multiple animal models of diabetes and in phase II clinical trials. However, the mechanism of PM therapeutic action is poorly understood. One potential mechanism is scavenging of pathogenic reactive carbonyl species (RCS) found to be elevated in diabetes. We have suggested previously that the pathogenicity of RCS methylglyoxal (MGO) may be due to modification of critical arginine residues in matrix proteins and interference with renal cell-matrix interactions. We have also shown that this MGO effect can be inhibited by PM (Pedchenko et al. (2005) Diabetes 54, 2952-2960). These findings raised the questions of whether the effect is specific to MGO, whether other structurally different physiological RCS can act via the same mechanism, and whether their action is amenable to PM protection. In the present study, we have shown that the important physiological RCS 3-deoxyglucosone (3-DG) can damage protein functionality, including the ability of collagen IV to interact with glomerular mesangial cells. We have also demonstrated that PM can protect against 3-DG-induced protein damage via a novel mechanism that includes transient adduction of 3-DG by PM followed by irreversible PM-mediated oxidative cleavage of 3-DG. Our results suggest that, in diabetic nephropathy, the therapeutic effect of PM is achieved, in part, via protection of renal cell-matrix interactions from damage by a variety of RCS. Our data emphasize the potential importance of the contribution by 3-DG, along with other more reactive RCS, to this pathogenic mechanism.

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Section: Methodsmentioning

confidence: 99%

Pyridoxamine Protects Proteins from Functional Damage by 3-Deoxyglucosone: Mechanism of Action of Pyridoxamine

et al. 2007

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“…enopyranoside(6) .-The bisdithiocarbonate (5b) (185 mg) and tri-n-butylstannane, treated as above, gave the alkene (6) (49 mg, 49y0), m.p. 158-160" (from ethanol) (Iit.,lg 163-164"), [ u ] , ~~ -105" (c 0.7) (lit.,l9 -130").…”

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confidence: 99%

“…(CHC1,) 1 160, 1 135, 1 110, and 1050 cm-l, Amy. 283 nni (o 22 300), r(CDC1,) 2.58 (5 H, in, aryl-H), 4.0-4.5(3 H, m, 2-and 3-H and PhCH), 5.04 (1 H, s), 5.6-6.16 (4 H, m),6.6 (3 H , s, OMe), and 7.47 and 7.68 (6 H, 2s, SMe), m/e 355 (Found: C, 46.85; H, 4.8. C18H,,06S, requires C, 46.7; H, 4.8%).…”

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confidence: 99%

Reactions of relevance to the chemistry of aminoglycoside antibiotics. Part 11. Preparation of olefins from vicinal diols

Barrett¹,

Barton²,

Bielski³

1979

J. Chem. Soc., Perkin Trans. 1

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Vicinal diols are converted in high yield into olefins by reaction of the derived bisdithiocarbonates with tri-n-butylstannane in toluene or benzene. The stereochemistry of reaction is consistent with a stepwise radical fragmentation. College, London SW7 2AYRECENTLY, carbohydrate esters containing the thiocarbonyl group have found application in novel mild procedures whereby hydroxy-functions may be selec-tively replaced by hydrogen or halide~.~93 For example, the reaction of 0-alkyl-S-methyldithiocarbonates (xanthates) with methyl iodide gave the iodoalkane and di-S-reduction of xanthates with tri-n-butylstannane gave the deoxy-compound via a radical fragmentation (Scheme 1). Substitution in the P-position of the intermediate alkyl radical by a good radical leaving group should permit the synthesis of alkenes. Herein is described the conversion of vicinal diols into alkenes by the radical fragmentation of the derived bis-xantliates (Scheme Attempts to prepare bisthioxobenzoates from vicinal diols using the Vilsmeier reagent (Me,&=CClPhd) were unsuccessful due t o formation of 1,2-chlorobenzoates via the cation (1) (Scheme 3).5 Since the preparation of xanthates proceeds via anionic intermediates, species analogous with the cation (1) cannot be formed. Consistent with this and literature p r e~e d e n t ,~.~ a series of carbohydrate diols (2a), (3a), (5a), and (7a) were converted into the bis-xanthates (2b), (3b), (5b), and (7b), respectively, using sodium hydride (catalysed by imidazole), carbon disulphide, and methyl iodide in sequence in tetrahydrofuran (THF), as detailed previously for monoxanthates. Formation of the bisxanthates was consistent with spectra and. microana-2) .4 RHR + Bunj Sn' _____) R R\ / I Bun3SnSCOSMe SCHEME 2 methyldithiocarbonate via S-methylation followed by SN2 displacement by iodide anion. Alternatively, properties in agreement with literature values.6 and S.

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