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

Liu, Wen-chi and Oikawa, Masato and Fukase, Koichi and Suda, Yasuo and Winarno, Hendig and Mosi, Saeko (1997) Enzymatic Preparation of (S)-3-Hydroxytetradecanoic Acid and Synthesis of Unnatural Analogues of Lipid A Containing the (S)-Acid. Bulletin of the Chemical Society of Japan, 70 (6). pp. 1441-1450.

[img] Text (Enzymatic Preparation of (S)-3-Hydroxytetradecanoic Acid and Synthesis of Unnatural Analogues of Lipid A Containing the (S)-Acid)
bcsj.70.1441

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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.

Item Type: Article
Subjects: Isotop dan Radiasi > Pemanfaatan Isotop dan Radiasi > Bidang Kesehatan
Divisions: Pusat Aplikasi Isotop dan Radiasi
Depositing User: USER PAIR BATAN
Date Deposited: 27 May 2018 15:08
Last Modified: 27 May 2018 15:08
URI: http://repo-nkm.batan.go.id/id/eprint/2427

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