Thio-click approach to the synthesis of stable glycomimetics

László Lázár, Magdolna Csávás, Marietta Tóth, László Somsák, Anikó Borbá

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Carbon-sulfur-bridged glycomimetics were prepared by free radical hydrothiolation of the exocyclic double bond of unsaturated sugars. Reaction between benzoyl-substituted pyranoid-exoglycal and a range of thiols including peptide, 1-thioglycerol and 1-thiosugar derivatives gave β-Dconfigured carbon-sulfur-linked glycoconjugates with full stereoselectivity. Addition of a panel of thiols to a 3-exomethylene-glucofuranose derivative also proceeded in a stereoselective manner and afforded a series of D-allo-configured 3-deoxy-3-C-S-bridged glycoconjugates.

Original languageEnglish
Pages (from-to)889-895
Number of pages7
JournalChemical Papers
Volume69
Issue number6
DOIs
Publication statusPublished - Jun 1 2015

Fingerprint

Glycoconjugates
Sulfur
Sulfhydryl Compounds
Thiosugars
Carbon
Derivatives
Stereoselectivity
Free radicals
Sugars
Peptides
Free Radicals
thioglycerol

Keywords

  • 3-exomethylene-furanose hydrothiolation
  • exoglycal
  • glycoconjugate
  • glycopeptide
  • photocatalysis
  • radical

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Biochemistry
  • Industrial and Manufacturing Engineering
  • Materials Chemistry

Cite this

Thio-click approach to the synthesis of stable glycomimetics. / Lázár, László; Csávás, Magdolna; Tóth, Marietta; Somsák, László; Borbá, Anikó.

In: Chemical Papers, Vol. 69, No. 6, 01.06.2015, p. 889-895.

Research output: Contribution to journalArticle

Lázár, László ; Csávás, Magdolna ; Tóth, Marietta ; Somsák, László ; Borbá, Anikó. / Thio-click approach to the synthesis of stable glycomimetics. In: Chemical Papers. 2015 ; Vol. 69, No. 6. pp. 889-895.
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