- Enzymatic preparation of (S)-3-hydroxytetradecanoic acid and synthesis of unnatural analogues of lipid A containing the (S)-acid
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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 IV(A), 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.
- Liu, Wen-Chi,Oikawa, Masato,Fukase, Koichi,Suda, Yasuo,Winarno, Hendig,Mori, Saeko,Hashimoto, Masahito,Kusumoto, Shoichi
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p. 1441 - 1450
(2007/10/03)
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- Towards the Chemoenzymatic Synthesis of Lipid A
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New procedures have been developed for the synthesis of the two important components of lipid A; one is the lipase-catalyzed resolution of 3-hydroxytetradecanoic acid in tetrahydrofuran using vinyl acetate and the other is the synthesis of the disaccharide moiety using glycosylphosphite as the glycosylating reagent.
- Sugai, Takeshi,Ritzen, Helena,Wong, Chi-Huey
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p. 1051 - 1058
(2007/10/02)
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