Synthesis of new PCDA-carbohydrate derivatives

Nitinkumar S. Shetty, Jae Ho Jeon, Chuljin Ahn

Research output: Contribution to journalArticle

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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Carbohydrates
Derivatives
Acids
Glucose
Amides
Acetates
Azides
Ammonium Compounds
Methanol
Salts
Galactose
Chlorides
Coloring Agents
Dyes
Sodium

All Science Journal Classification (ASJC) codes

  • Chemical Engineering (miscellaneous)
  • Chemistry (miscellaneous)

Cite this

Shetty, Nitinkumar S. ; Jeon, Jae Ho ; Ahn, Chuljin. / Synthesis of new PCDA-carbohydrate derivatives. In: Journal of the Korean Chemical Society. 2010 ; Vol. 54, No. 5. pp. 650-652.
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Synthesis of new PCDA-carbohydrate derivatives. / Shetty, Nitinkumar S.; Jeon, Jae Ho; Ahn, Chuljin.

In: Journal of the Korean Chemical Society, Vol. 54, No. 5, 20.10.2010, p. 650-652.

Research output: Contribution to journalArticle

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AB - 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.

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