Synthesis of new PCDA-carbohydrate derivatives

Nitinkumar S. Shetty, Jae Ho Jeon, Chuljin Ahn

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Abstract

The synthesis of new 10,12-pentacosadynoic acid (PCDA), which is a tagging carbohydrates with PCDA dye was examined. The β-D-glucose penta-acetate was transformed into corresponding β-azide. β-D-glucose pentaacetate azide was reduced with p-toluenesulfonic acid to get carbohydrate p-TSA ammonium salt in good yield. The crude 10,12-pentacosadynoyl chloride which was in turn prepared from the PCDA and oxalyl chloride was react with p-TSA ammonium salt to get the glucose acetate derivative with PCDA tail. The glucose acetate derivative has undergone deprotection reaction with methanol and sodium methoxide to get the carbohydrate-PCDA amide 5 with 55% yield. The galactose-PCDA amide was synthesized by the deprotection of galactose pentaacetate-PCDA amide with 45% yield.

Original languageEnglish
Pages (from-to)650-652
Number of pages3
JournalJournal of the Korean Chemical Society
Volume54
Issue number5
DOIs
Publication statusPublished - 20-10-2010

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All Science Journal Classification (ASJC) codes

  • Chemical Engineering (miscellaneous)
  • Chemistry (miscellaneous)

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