Synthesis and antioxidant capacity of 5-selenopyranose derivatives

Corin Storkey; Michael Jonathan Davies; Jonathan M White; Carl H Schiesser

doi:10.1039/c1cc13652f

Synthesis and antioxidant capacity of 5-selenopyranose derivatives

Corin Storkey, Michael Jonathan Davies, Jonathan M White, Carl H Schiesser

26 Citations (Scopus)

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.

Original language	English
Journal	Chemical communications (Cambridge, England)
Volume	47
Issue number	34
Pages (from-to)	9693-5
Number of pages	3
ISSN	1359-7345
DOIs	https://doi.org/10.1039/c1cc13652f
Publication status	Published - 14 Sept 2011
Externally published	Yes

Keywords

Antioxidants
Blood Proteins
Humans
Organometallic Compounds
Oxidants
Oxidation-Reduction
Peroxidase
Selenium
Sulfides

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10.1039/c1cc13652f

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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",

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doi = "10.1039/c1cc13652f",

language = "English",

volume = "47",

pages = "9693--5",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "34",

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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

SN - 1359-7345

VL - 47

SP - 9693

EP - 9695

JO - Chemical Communications

JF - Chemical Communications

IS - 34

ER -

Synthesis and antioxidant capacity of 5-selenopyranose derivatives

Abstract

Keywords

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