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Enzymatic Preparation of ( S )-3-Hydroxytetradecanoic Acid and Synthesis of Unnatural Analogues of Lipid A Containing the ( S )-Acid

1997; Oxford University Press; Volume: 70; Issue: 6 Linguagem: Inglês

10.1246/bcsj.70.1441

1348-0634

Wen-Chi Liu, Masato Oikawa, Koichi Fukase, Yasuo Suda, Hendig Winarno, Saeko Mori, Masahito Hashimoto, Shoichi Kusumoto,

Glycosylation and Glycoproteins Research

Abstract Synthesis of unnatural analogues, that contain (S)-3-hydroxytetradecanoyl moieties in place of the corresponding natural (R)-isomers, of both lipid A and its biosynthetic precursor, designated precursor Ia or lipid IVA, has been achieved through our recently developed procedure. (S)-3-Hydroxytetradecanoic acid was prepared from its racemate through the optical resolution by the use of a lipase and subsequent fractional recrystallization. The (S)-acyl analogue of lipid A exhibited slightly stronger interleukin-6 inducing activity than the corresponding natural lipid A, and the (S)-acyl analogue of the biosynthetic precursor was far more active than the natural precursor in inhibiting the induction of interleukin-6 by lipopolysaccharide.