Synthesis and antioxidant capacity of 5-selenopyranose derivatives

Research output: Contribution to journal › Journal article › peer-review

Standard

Synthesis and antioxidant capacity of 5-selenopyranose derivatives. / Storkey, Corin; Davies, Michael Jonathan; White, Jonathan M; Schiesser, Carl H.

In: Chemical communications (Cambridge, England), Vol. 47, No. 34, 14.09.2011, p. 9693-5.

Research output: Contribution to journal › Journal article › peer-review

Harvard

Storkey, C, Davies, MJ, White, JM & Schiesser, CH 2011, 'Synthesis and antioxidant capacity of 5-selenopyranose derivatives', Chemical communications (Cambridge, England), vol. 47, no. 34, pp. 9693-5. https://doi.org/10.1039/c1cc13652f

APA

Storkey, C., Davies, M. J., White, J. M., & Schiesser, C. H. (2011). Synthesis and antioxidant capacity of 5-selenopyranose derivatives. Chemical communications (Cambridge, England), 47(34), 9693-5. https://doi.org/10.1039/c1cc13652f

Vancouver

Storkey C, Davies MJ, White JM, Schiesser CH. Synthesis and antioxidant capacity of 5-selenopyranose derivatives. Chemical communications (Cambridge, England). 2011 Sep 14;47(34):9693-5. https://doi.org/10.1039/c1cc13652f

Author

Storkey, Corin ; Davies, Michael Jonathan ; White, Jonathan M ; Schiesser, Carl H. / Synthesis and antioxidant capacity of 5-selenopyranose derivatives. In: Chemical communications (Cambridge, England). 2011 ; Vol. 47, No. 34. pp. 9693-5.

Bibtex

@article{eea59dc9f03c48ea93e150a20c18e68b,
title = "Synthesis and antioxidant capacity of 5-selenopyranose derivatives",
abstract = "Described is a convenient method for the syntheses of sulfur and selenium containing carbohydrate derivatives of L-gulodeoxynojirimycin and the corresponding C-5 epimer D-mannodeoxynojirimycin. The key step in the synthesis of the latter involves epimerisation of the C-5 hydroxyl group by an oxidation followed by stereo-selective reduction to obtain the desired D-sugar derivative. Both derivatives displayed a dose-dependent prevention of the oxidation of methionine residues on human plasma proteins induced by the inflammatory oxidant hypochlorous acid. The seleno-analogues were considerably more active than their thio-equivalents.",
keywords = "Antioxidants, Blood Proteins, Humans, Organometallic Compounds, Oxidants, Oxidation-Reduction, Peroxidase, Selenium, Sulfides",
author = "Corin Storkey and Davies, {Michael Jonathan} and White, {Jonathan M} and Schiesser, {Carl H}",
note = "This journal is {\textcopyright} The Royal Society of Chemistry 2011",
year = "2011",
month = sep,
day = "14",
doi = "10.1039/c1cc13652f",
language = "English",
volume = "47",
pages = "9693--5",
journal = "Chemical Communications",
issn = "1359-7345",
publisher = "Royal Society of Chemistry",
number = "34",

}

RIS

TY - JOUR

T1 - Synthesis and antioxidant capacity of 5-selenopyranose derivatives

AU - Storkey, Corin

AU - Davies, Michael Jonathan

AU - White, Jonathan M

AU - Schiesser, Carl H

N1 - This journal is © The Royal Society of Chemistry 2011

PY - 2011/9/14

Y1 - 2011/9/14

N2 - Described is a convenient method for the syntheses of sulfur and selenium containing carbohydrate derivatives of L-gulodeoxynojirimycin and the corresponding C-5 epimer D-mannodeoxynojirimycin. The key step in the synthesis of the latter involves epimerisation of the C-5 hydroxyl group by an oxidation followed by stereo-selective reduction to obtain the desired D-sugar derivative. Both derivatives displayed a dose-dependent prevention of the oxidation of methionine residues on human plasma proteins induced by the inflammatory oxidant hypochlorous acid. The seleno-analogues were considerably more active than their thio-equivalents.

AB - Described is a convenient method for the syntheses of sulfur and selenium containing carbohydrate derivatives of L-gulodeoxynojirimycin and the corresponding C-5 epimer D-mannodeoxynojirimycin. The key step in the synthesis of the latter involves epimerisation of the C-5 hydroxyl group by an oxidation followed by stereo-selective reduction to obtain the desired D-sugar derivative. Both derivatives displayed a dose-dependent prevention of the oxidation of methionine residues on human plasma proteins induced by the inflammatory oxidant hypochlorous acid. The seleno-analogues were considerably more active than their thio-equivalents.

KW - Antioxidants

KW - Blood Proteins

KW - Humans

KW - Organometallic Compounds

KW - Oxidants

KW - Oxidation-Reduction

KW - Peroxidase

KW - Selenium

KW - Sulfides

U2 - 10.1039/c1cc13652f

DO - 10.1039/c1cc13652f

M3 - Journal article

C2 - 21799982

VL - 47

SP - 9693

EP - 9695

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

IS - 34

ER -

ID: 129669663