Synthesis of glycyrrhizin analogues containing fluorinated beta(1->2)-linked disaccharides

被引：6

作者：

Morishima, N ^{[1
]}

Mori, Y ^{[1
]}

机构：

[1] KITASATO UNIV,SCH NURSING,SAGAMIHARA,KANAGAWA 228,JAPAN

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 1996年 / 4卷 / 11期

关键词：

glycyrrhizin; fluorinated disaccharide; glycosylation;

D O I：

10.1016/S0968-0896(96)00169-1

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

For studies on the recognition mechanisms for Glycyrrhizin-induced biological activities, seven Glycyrrhizin analogues with 3'-,4'-,6'-,3-, and 4-fluorinated 2-O-beta-D-glucopyranosyl-beta-D-glucopyranoses (1-5) and 3- and 4-fluorinated 2-O-beta-D-glucopyranuronosyl-beta-D-glucopyranoses (6 and 7) were synthesized through a stepwise glycosylation procedure. 1,2-Di-O-acetyl-4,6-di-0-benzyl-3-deoxy-3-fluoro- (13) and 1,2-di-O-acetyl-3,6-di-O-benzyl-4-deoxy-4-fluoro-D-glucopyranose (14) were employed for the first beta-glycosylation of methyl glycyrrhetate, promoted with trimethylsilyl trifluoromethanesulfonate. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：1799 / 1808

页数：10

共 21 条

[1] INTERFERON INDUCTION BY GLYCYRRHIZIN AND GLYCYRRHETINIC ACID IN MICE [J].

ABE, N ;

EBINA, T ;

ISHIDA, N .

MICROBIOLOGY AND IMMUNOLOGY, 1982, 26 (06) :535-539

[2] 4-DEOXY-4-FLUORO-D-GLUCOSE [J].

BARFORD, AD ;

FOSTER, AB ;

WESTWOOD, JH .

CARBOHYDRATE RESEARCH, 1969, 11 (02) :287-&

[3] BETA-ELIMINATION IN URONIC ACIDS - EVIDENCE FOR AN ELCB MECHANISM [J].

BEMILLER, JN ;

KUMARI, GV .

CARBOHYDRATE RESEARCH, 1972, 25 (02) :419-428

[4]

FEHLHABER HW, 1987, LIEBIGS ANN CHEM, P637

[5] THE ANTI-INFLAMMATORY ACTIVITY OF GLYCYRRHETINIC ACID AND DERIVATIVES [J].

FINNEY, RSH ;

SOMERS, GF .

JOURNAL OF PHARMACY AND PHARMACOLOGY, 1958, 10 (10) :613-620

[6]

Foster A. B., 1970, Canadian Journal of Chemistry, V48, P3937, DOI 10.1139/v70-659

[7] SYNTHESIS OF BETA-GLYCOSIDES OF GLYCYRRHETIC ACID [J].

HIROOKA, M ;

MORISHIMA, N ;

KAJI, E ;

MORI, Y ;

ZEN, S .

YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1989, 109 (08) :544-559

[8]

ISHIKAWA A, 1990, BIOCH BIOPHSY RES CO, V167, P878

[9] SYNTHESIS OF O-]-BETA-D-GLUCOPYRANOSYL-(1-]2)-O-BETA-D-GLUCOPYRANOSYL-(1-]6)-D-GLUCOPYRANOSE - DEHYDRATIVE BETA-D-GLUCOSYLATION USING 2-O-ACETYL-3,4,6-TRI-O-BENZYL-D-GLUCOPYRANOSE [J].

KOTO, S ;

MORISHIMA, N ;

SATO, H ;

SATO, Y ;

ZEN, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1985, 58 (01) :120-122

[10] STEREOSELECTIVE ALPHA-GLUCOSYLATION WITH TETRA-O-BENZYL-ALPHA-D-GLUCOSE AND A MIXTURE OF TRIMETHYLSILYL BROMIDE, COBALT(II) BROMIDE, TETRABUTYLAMMONIUM BROMIDE, AND A MOLECULAR-SIEVE - A SYNTHESIS OF 3,6-DI-O-(ALPHA-D-GLUCOPYRANOSYL)-D-GLUCOSE [J].

KOTO, S ;

MORISHIMA, N ;

KUSUHARA, C ;

SEKIDO, S ;

YOSHIDA, T ;

ZEN, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1982, 55 (09) :2995-2999

← 1 2 3 →