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

doi:10.1016/j.bmc.2006.05.051

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 journal › Article

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 language	English
Pages (from-to)	6759-6777
Number of pages	19
Journal	Bioorganic and Medicinal Chemistry
Volume	14
Issue number	19
DOIs	https://doi.org/10.1016/j.bmc.2006.05.051
Publication status	Published - 2006 Oct 1
Externally published	Yes

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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

Akamatsu, M., Fujimoto, Y., Kataoka, M., Suda, Y., Kusumoto, S., & Fukase, K. (2006). Synthesis of lipid A monosaccharide analogues containing acidic amino acid: Exploring the structural basis for the endotoxic and antagonistic activities. Bioorganic and Medicinal Chemistry, 14(19), 6759-6777. https://doi.org/10.1016/j.bmc.2006.05.051

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 journal › Article

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10.1016/j.bmc.2006.05.051