Total synthesis of a glycoglycerolipid from Meiothermus taiwanensis through a one-pot glycosylation reaction and exploration of its immunological properties

Bhaswati Ghosh, Yen Hsun Lai, Yu Yin Shih, Tapan Kumar Pradhan, Chun Hung Lin*, Kwok-Kong Mong

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

The total synthesis of a glycoglycerolipid isolate of Meiothermus taiwanensis and its truncated structural analogues is reported. Our synthesis employed DMF-modulated and low-concentration glycosylation reactions for the construction of α- and β-glycosidic bonds in the absence of participating protecting groups. Further simplification of the synthesis was achieved by employing a low-concentration one-pot glycosylation procedure. Preliminary immunological studies showed that one of the truncated structural analogues suppressed the cytokine production of THP-1 monocytes.

Original languageEnglish
Pages (from-to)3191-3199
Number of pages9
JournalChemistry - An Asian Journal
Volume8
Issue number12
DOIs
StatePublished - 1 Dec 2013

Keywords

  • glycosylation
  • immunology
  • lipids
  • natural products
  • total synthesis

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