Exploring the Syntheses of Novel Glycomimetics. Carbohydrate Derivatives with Se-S- or Se-Se- Glycosidic Linkages

Tünde Zita Illyés, Sára Balla, A. Bényei, Ambati Ashok Kumar, István Timári, K. Kövér, László Szilágyi

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

A convenient route to Se-S-glycoside derivatives was developed using glycosyl isoselenuronium salts as glycosylselenenyl transfer reagents toward thiols. Aliphatic and aromatic thiols were found to react in the presence of N,N-diisopropylethylamine as a base and furnished alkyl- or aryl glycosylselenenylsulfide derivatives. S-glycosylselenenyl-cysteines were obtained similarly via reactions with O,N-protected cysteine. Reactions with monosaccharide thiols provided disaccharide mimics featuring Se-S- interglycosidic bonds. Further disaccharide mimics with Se-Se interglycosidic linkage were obtained from the starting isoselenuronium salts via reactions with protected monosaccharide derivatives bearing selenol groups in 6- or 4-position. The novel glycomimetics are expected to open new perspectives in biological activities and/or mechanistic studies due, i.a., to the rather uncommon Se-S- or Se-Se bonds incorporated into a carbohydrate framework.

Original languageEnglish
Pages (from-to)2383-2388
Number of pages6
JournalChemistrySelect
Volume1
Issue number10
DOIs
Publication statusPublished - Jan 1 2016

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Sulfhydryl Compounds
Monosaccharides
Disaccharides
Carbohydrates
Derivatives
Cysteine
Bearings (structural)
Salts
Glycosides
Bioactivity

Keywords

  • Carbohydrate
  • Se-Se-bond
  • selenenylsulfide
  • selenosugar

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Exploring the Syntheses of Novel Glycomimetics. Carbohydrate Derivatives with Se-S- or Se-Se- Glycosidic Linkages. / Illyés, Tünde Zita; Balla, Sára; Bényei, A.; Kumar, Ambati Ashok; Timári, István; Kövér, K.; Szilágyi, László.

In: ChemistrySelect, Vol. 1, No. 10, 01.01.2016, p. 2383-2388.

Research output: Contribution to journalArticle

Illyés, Tünde Zita ; Balla, Sára ; Bényei, A. ; Kumar, Ambati Ashok ; Timári, István ; Kövér, K. ; Szilágyi, László. / Exploring the Syntheses of Novel Glycomimetics. Carbohydrate Derivatives with Se-S- or Se-Se- Glycosidic Linkages. In: ChemistrySelect. 2016 ; Vol. 1, No. 10. pp. 2383-2388.
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