STEREOCONTROLLED INTRODUCTION OF DEUTERIUM ATOMS INTO A PHYTOALEXIN ELICITOR-ACTIVE BETA-D-GLUCOHEXAOSIDE

被引：14

作者：

HONG, N ^{[1
]}

NAKAHARA, Y ^{[1
]}

OGAWA, T ^{[1
]}

机构：

[1] UNIV TOKYO,FAC AGR,BUNKYO KU,TOKYO 113,JAPAN

来源：

PROCEEDINGS OF THE JAPAN ACADEMY SERIES B-PHYSICAL AND BIOLOGICAL SCIENCES | 1993年 / 69卷 / 03期

关键词：

STEREOCONTROLLED SYNTHESIS; DEUTERIUM LABELING; PHYTOALEXIN ELICITOR;

D O I：

10.2183/pjab.69.55

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

Stereocontrolled deuterium labelling of phytoalexin elicitor-active beta-D-glucohexaoside 2 was executed by employing a stereospecifically deuterated D-glucose derivative 11 as a starting material. As a result, unambiguous assignment of the anomeric signals in H-1-NMR of compound 2 was achieved by use of the deuterated compounds 3, 4, and 5.

引用

收藏

页码：55 / 60

页数：6

相关论文

共 21 条

[1] SOME STEREOCHEMICAL CHARACTERISTICS OF C-H-1-C-H-2 EXCHANGE-REACTIONS WITH RANEY-NICKEL CATALYST IN DEUTERIUM-OXIDE [J].

BALZA, F ;

PERLIN, AS .

CARBOHYDRATE RESEARCH, 1982, 107 (02) :270-278

[2] 1,2-ORTHOACETATE INTERMEDIATES IN SILVER TRIFLUOROMETHANESULFONATE PROMOTED KOENIGS-KNORR SYNTHESIS OF DISACCHARIDE GLYCOSIDES [J].

BANOUB, J ;

BUNDLE, DR .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1979, 57 (16) :2091-2097

[3] STRUCTURE-ACTIVITY-RELATIONSHIPS OF OLIGO-BETA-GLUCOSIDE ELICITORS OF PHYTOALEXIN ACCUMULATION IN SOYBEAN [J].

CHEONG, JJ ;

BIRBERG, W ;

FUGEDI, P ;

PILOTTI, A ;

GAREGG, PJ ;

HONG, N ;

OGAWA, T ;

HAHN, MG .

PLANT CELL, 1991, 3 (02) :127-136

[4] SELECTIVE CLEAVAGE OF ANOMERIC ACETYL GROUPS OF ACETYLATED GLYCOSYL RESIDUES BY HYDRAZINE [J].

EXCOFFIER, G ;

GAGNAIRE, D ;

UTILLE, JP .

CARBOHYDRATE RESEARCH, 1975, 39 (02) :368-373

[5] SYNTHESES OF A BRANCHED HEPTASACCHARIDE HAVING PHYTO-ALEXIN-ELICITOR ACTIVITY [J].

FUGEDI, P ;

BIRBERG, W ;

GAREGG, PJ ;

PILOTTI, A .

CARBOHYDRATE RESEARCH, 1987, 164 :297-312

[6]

FUGEDI P, 1989, J CARBOHYD CHEM, V8, P47

[7] PARA-ANISYL GROUP - A VERSATILE PROTECTING GROUP FOR PRIMARY ALCOHOLS [J].

FUKUYAMA, T ;

LAIRD, AA ;

HOTCHKISS, LM .

TETRAHEDRON LETTERS, 1985, 26 (51) :6291-6292

[8] STUDIES ON KOENIGS-KNORR GLYCOSIDATIONS [J].

GAREGG, PJ ;

KONRADSSON, P ;

KVARNSTROM, I ;

NORBERG, T ;

SVENSSON, SCT ;

WIGILIUS, B .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1985, 39 (07) :569-577

[9]

HONG N, 1990, TETRAHEDRON LETT, V31, P3179

[10] CATALYTIC C-DEUTERATION OF SOME CARBOHYDRATE-DERIVATIVES [J].

KOCH, HJ ;

STUART, RS .

CARBOHYDRATE RESEARCH, 1978, 67 (02) :341-348