Chemical Glycosylations for the Synthesis of Building Units of Post-Translational Modifications

Bahareh Shirinfar, Nisar Ahmed

Research output: Contribution to journalArticle (Academic Journal)peer-review

1 Citation (Scopus)

Abstract

In chemical glycosylation reactions, a glycosyl donor couples with a glycosyl acceptor through glycosidic linkage. Most of the products end up with a mixture due to the formation of a stereogenic center at the anomeric carbon. Activation with a suitable Lewis acid and introduction of the non-participating protecting group on donor and acceptor results in a selective product. Herein, we used a suitably protected donor and acceptor which produced an orthogonally protected building block with α-selectivity. We used also a donor for the synthesis of modified phosphoribosylated amino acid. The formation of glycoside products can be used to synthesize complex biologically important organic molecules.

Original languageEnglish
Article numbere1700226
JournalHelvetica Chimica Acta
Volume101
Issue number1
DOIs
Publication statusPublished - 1 Jan 2018

Keywords

  • adenosine
  • amino acid
  • glycosidic bond
  • glycosylation
  • post-translational modification
  • riboside

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