Bivalent glycoconjugates based on 1,5-diazabicyclo[3.3.0]octa-3,6-diene-2,8-dione (“bimane”) as a central scaffold

Tamás Szabó, A. Bényei, László Szilágyi

Research output: Article

Abstract

The heteroaromatic fused diazabicyclic “bimane” ring system, discovered four decades ago, is endowed with remarkable chemical and photophysical properties. No carbohydrate derivatives of bimanes have, however, been described thus far. Here we report on the syntheses of a range of bimanes decorated with various glycosyl residues. Mono- and disaccharide residues were attached to syn- or anti-bimane central cores via thio-, disulfido- or selenoglycosidic linkages to obtain novel fluorescent or nonfluorescent glycoconjugates. Cu(I)-catalyzed cycloaddition of glycosyl azides to a bimane diethynyl derivative furnished further bivalent glycoconjugates with sugar residues linked to the central bimane core via 1,2,3-triazole rings. We have determined the crystal and molecular structures of several glycosylated and non-glycosylated bimanes and report fluorescence data for the new compounds.

Original languageEnglish
Pages (from-to)88-98
Number of pages11
JournalCarbohydrate Research
Volume473
DOIs
Publication statusPublished - febr. 1 2019

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Glycoconjugates
Scaffolds
Derivatives
Triazoles
Azides
Cycloaddition
Monosaccharides
Disaccharides
Cycloaddition Reaction
bimanes
Molecular Structure
Sugars
Molecular structure
Crystal structure
Fluorescence
Carbohydrates

Keywords

    ASJC Scopus subject areas

    • Analytical Chemistry
    • Biochemistry
    • Organic Chemistry

    Cite this

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    title = "Bivalent glycoconjugates based on 1,5-diazabicyclo[3.3.0]octa-3,6-diene-2,8-dione (“bimane”) as a central scaffold",
    abstract = "The heteroaromatic fused diazabicyclic “bimane” ring system, discovered four decades ago, is endowed with remarkable chemical and photophysical properties. No carbohydrate derivatives of bimanes have, however, been described thus far. Here we report on the syntheses of a range of bimanes decorated with various glycosyl residues. Mono- and disaccharide residues were attached to syn- or anti-bimane central cores via thio-, disulfido- or selenoglycosidic linkages to obtain novel fluorescent or nonfluorescent glycoconjugates. Cu(I)-catalyzed cycloaddition of glycosyl azides to a bimane diethynyl derivative furnished further bivalent glycoconjugates with sugar residues linked to the central bimane core via 1,2,3-triazole rings. We have determined the crystal and molecular structures of several glycosylated and non-glycosylated bimanes and report fluorescence data for the new compounds.",
    keywords = "1,2,3-triazole, Disulfide, Fluorescence, Heteroaromatics, Selenoglycoside, Thioglycoside, X-ray structures",
    author = "Tam{\'a}s Szab{\'o} and A. B{\'e}nyei and L{\'a}szl{\'o} Szil{\'a}gyi",
    year = "2019",
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    AU - Szabó, Tamás

    AU - Bényei, A.

    AU - Szilágyi, László

    PY - 2019/2/1

    Y1 - 2019/2/1

    N2 - The heteroaromatic fused diazabicyclic “bimane” ring system, discovered four decades ago, is endowed with remarkable chemical and photophysical properties. No carbohydrate derivatives of bimanes have, however, been described thus far. Here we report on the syntheses of a range of bimanes decorated with various glycosyl residues. Mono- and disaccharide residues were attached to syn- or anti-bimane central cores via thio-, disulfido- or selenoglycosidic linkages to obtain novel fluorescent or nonfluorescent glycoconjugates. Cu(I)-catalyzed cycloaddition of glycosyl azides to a bimane diethynyl derivative furnished further bivalent glycoconjugates with sugar residues linked to the central bimane core via 1,2,3-triazole rings. We have determined the crystal and molecular structures of several glycosylated and non-glycosylated bimanes and report fluorescence data for the new compounds.

    AB - The heteroaromatic fused diazabicyclic “bimane” ring system, discovered four decades ago, is endowed with remarkable chemical and photophysical properties. No carbohydrate derivatives of bimanes have, however, been described thus far. Here we report on the syntheses of a range of bimanes decorated with various glycosyl residues. Mono- and disaccharide residues were attached to syn- or anti-bimane central cores via thio-, disulfido- or selenoglycosidic linkages to obtain novel fluorescent or nonfluorescent glycoconjugates. Cu(I)-catalyzed cycloaddition of glycosyl azides to a bimane diethynyl derivative furnished further bivalent glycoconjugates with sugar residues linked to the central bimane core via 1,2,3-triazole rings. We have determined the crystal and molecular structures of several glycosylated and non-glycosylated bimanes and report fluorescence data for the new compounds.

    KW - 1,2,3-triazole

    KW - Disulfide

    KW - Fluorescence

    KW - Heteroaromatics

    KW - Selenoglycoside

    KW - Thioglycoside

    KW - X-ray structures

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