Synthesis of a new class of glycolipids and the evaluation of their immunogenicity using murine splenocytes

A. Sandeep, Bonam Srinivasa Reddy, Irfan Hyder, Halmuthur M.Sampath Kumar

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

A new class of glycolipids were generated by the incorporation of lipid entities at the C-6 position of D-glucose through oxidation of the primary hydroxyl group of tetrabenzylated D-glucose to form corresponding aldehyde, which in turn was subjected to Grignard reaction with C8 and C16 alkyl magnesium halides. The resulting lipidated secondary alcohol was further subjected to esterification with long-chain carboxylic acids to afford novel glycolipids. All of the derivatives 4a–b, 6a–d, and 8a–b exhibited low cytotoxicity and induced strong T and B cell proliferation and IL-2, IL-4, and IFN-γ expression from stimulated splenocyte culture, signifying their potent immunostimulating activity.

Original languageEnglish (US)
Pages (from-to)326-343
Number of pages18
JournalJournal of Carbohydrate Chemistry
Volume35
Issue number6
DOIs
StatePublished - Jul 23 2016
Externally publishedYes

Keywords

  • Cytotoxicity
  • cytokines
  • glycolipids
  • grignard reaction
  • immunogenicity

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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