581. The reactivity of the O-acylglycosyl halides. Part III. Steric effects

Newth, F. H.; Phillips, Glyn O.

doi:10.1039/jr9530002904

Cited by 13 publications

(5 citation statements)

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“…A 180 mg yield of three-times-crystallized chromatographically pure p-nitrothiophenyl /l-D-xylopyranoside was obtained from 5 g of 2,3,4-tri-0-acetyl-/1-Dxylopyranosyl bromide (Newth & Phillips, 1953) (yield 4%), m.p. 146-148°C, [cx]" -79.1I (c 0.18 in methanol), H n.m.r.…”

Section: Chemicalsmentioning

confidence: 99%

Kinetic studies on the broad-specificity β-d-glucosidase from pig kidney

Pócsi

Kiss

1988

Biochemical Journal

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A broad-specificity beta-D-glucosidase from pig kidney cortex was isolated and purified to homogeneity by a rapid purification procedure. The pI (5.14 +/- 0.05), Mr (59,000 +/- 2000) and specific activities with several p-nitrophenyl glycosides (galactopyranoside, glucopyranoside, arabinopyranoside, xylopyranoside) were comparable with those published previously for cytoplasmic beta-D-glucosidase from other sources and organs. Mixed-substrate experiments and inhibition studies with glucono-(1----5)-lactone revealed that a single active centre, containing one catalytic site and one saccharide-binding site, was responsible for the splitting of all four synthetic substrates. Inhibition experiments with substrate analogues demonstrated that (i) the major binding determinant of the glycosides was the aglycone moiety, (ii) an anionic side chain of the enzyme (probably a carboxy group) interacted with the glycosidic linkages and (iii) the properties of the aglycone significantly influenced the binding of the carbohydrate moiety. The inhibition constants of the p-nitrothiophenyl derivatives were in good agreement with the Km values of the corresponding substrates. Therefore the Michaelis constants could be regarded as true equilibrium constants (Ks). The 'three-point-attachment model' of the substrate splitting, proposed by Daniels [(1983) Ph.D. Dissertation, University of Pittsburgh] for the analogous liver enzyme, was applicable for beta-D-glucosidase from pig kidney too. The possible nature of the 'attachments' is discussed.

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Section: Chemicalsmentioning

confidence: 99%

Kinetic studies on the broad-specificity β-d-glucosidase from pig kidney

Pócsi

Kiss

1988

Biochemical Journal

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“…The latter method is reported to give lower stereoselectivity and yield than the former. [11] Furthermore, xylosyl donors such as 2,3,4-tri-O-acetyl-β--xylosyl bromide have been reported to show too high a reactivity [12] to handle under anhydrous conditions. Therefore, the imidate method was selected for the xylosylation reaction in this case.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Conandroside: A Dihydroxyphenylethyl Glycoside fromConandron ramaidioides

et al. 2000

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“…The comparison of the results of Tables 1 and 2 confirms the fact known in the literature that 2deoxysugars are more reactive than the corresponding sugars. 54 The presence of 2-deoxy-D-ribose in thymidine makes its derivatives more reactive. Under conditions analogous to those for thymidine derivatives, in the case of uridine derivatives we have not been able to achieve any product.…”

Section: Discussionmentioning

confidence: 99%

Efficient synthesis and antifungal investigation of nucleosides’ quaternaryammonium salt derivatives

Dmochowska¹,

Pellowska-Januszek²,

Samaszko-Fiertek³

et al. 2019

Turk J Chem

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Quaternary ammonium salts are a group of compounds with diverse biological properties, the most important of which are their antiviral, antibacterial, and antifungal activities. The quaternization reactions of 5'-O-tosyl derivatives of uridine and thymidine with triethylamine, trimethylamine, 4-(N , N-dimethylamino)pyridine, 2-methylpyridine, and pyridine are described in this article. Two of the synthesized compounds are exceptional because they are first of this type that demonstrate concentration-dependent antifungal in vitro activity against two species of the genus Candida in minimal YNB-SG medium. The experimental results have been extended by adding full atom molecular dynamics simulations and substrates and products energies evaluation.

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581. The reactivity of the O-acylglycosyl halides. Part III. Steric effects

Cited by 13 publications

References 0 publications

Kinetic studies on the broad-specificity β-d-glucosidase from pig kidney

Kinetic studies on the broad-specificity β-d-glucosidase from pig kidney

Synthesis of Conandroside: A Dihydroxyphenylethyl Glycoside fromConandron ramaidioides

Efficient synthesis and antifungal investigation of nucleosides’ quaternaryammonium salt derivatives

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