Synthesis of a suite of click-compatible sugar analogs for probing carbohydrate metabolism

Bo Wang, Daniel D. McClosky, Charles T. Anderson, Gong Chen

Research output: Contribution to journalArticle

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Abstract

Metabolic labeling based on the click chemistry between alkynyl and azido groups offers a powerful tool to study the function of carbohydrates in living systems, including plants. Herein, we describe the chemical synthesis of six alkynyl-modified sugars designed as analogs to D-glucose, D-mannose, L-rhamnose and sucrose present in plant cell walls. Among these new alkynyl probes, four of them are the 6-deoxy-alkynyl analogs of the corresponding sugars and do not possess any 6-OH groups. The other two are based on a new structural design, in which an ethynyl group is incorporated at the C-6 position of the sugar and the 6-OH group remains. The synthetic routes for both types of probes share common aldehyde intermediates, which are derived from the corresponding 6-OH precursor with other hydroxy groups protected. The overall synthesis sequence of these probes is efficient, concise, and scalable.

Original languageEnglish (US)
Pages (from-to)54-62
Number of pages9
JournalCarbohydrate Research
Volume433
DOIs
StatePublished - Jan 1 2016

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All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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