Synthesis of lipid A monosaccharide analogues containing acidic amino acid: Exploring the structural basis for the endotoxic and antagonistic activities

Masao Akamatsu, Yukari Fujimoto, Mikayo Kataoka, Yasuo Suda, Shoichi Kusumoto, Koichi Fukase

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

For elucidation of the structural and conformational requirements on the endotoxic and antagonistic activity of lipid A derivatives, we designed and synthesized lipid A analogues containing acidic amino acid residues in place of the non-reducing end phosphorylated glucosamine. Definite switching of the endotoxic or antagonistic activity was observed depending on the difference of the acidic groups (phosphoric acid or carboxylic acid) in the lipid A analogues.

Original languageEnglish
Pages (from-to)6759-6777
Number of pages19
JournalBioorganic and Medicinal Chemistry
Volume14
Issue number19
DOIs
Publication statusPublished - 2006 Oct 1
Externally publishedYes

Fingerprint

Acidic Amino Acids
Lipid A
Monosaccharides
Glucosamine
Carboxylic Acids
Derivatives

Keywords

  • Cytokine induction
  • Endotoxin
  • IL-6
  • Innate immunity
  • Lipid A

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

Synthesis of lipid A monosaccharide analogues containing acidic amino acid : Exploring the structural basis for the endotoxic and antagonistic activities. / Akamatsu, Masao; Fujimoto, Yukari; Kataoka, Mikayo; Suda, Yasuo; Kusumoto, Shoichi; Fukase, Koichi.

In: Bioorganic and Medicinal Chemistry, Vol. 14, No. 19, 01.10.2006, p. 6759-6777.

Research output: Contribution to journalArticle

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