Enzymatic preparation of (S)-3-hydroxytetradecanoic acid and synthesis of unnatural analogues of lipid a containing the (S)-acid

被引：19

作者：

Liu, WC ^{[1
]}

Oikawa, M ^{[1
]}

Fukase, K ^{[1
]}

Suda, Y ^{[1
]}

Winarno, H ^{[1
]}

Mori, S ^{[1
]}

Hashimoto, M ^{[1
]}

Kusumoto, S ^{[1
]}

机构：

[1] OSAKA UNIV, GRAD SCH SCI, DEPT CHEM, TOYONAKA, OSAKA 560, JAPAN

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1997年 / 70卷 / 06期

关键词：

D O I：

10.1246/bcsj.70.1441

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：1441 / 1450

页数：10

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