2,5-DIDEOXY-2,5-IMINO-D-MANNITOL AND -D-GLUCITOL - 2-STEP BIOORGANIC SYNTHESES FROM 5-AZIDO-5-DEOXY-D-GLUCOFURANOSE AND -L-IDOFURANOSE - EVALUATION AS GLUCOSIDASE INHIBITORS AND APPLICATION IN AFFINITY PURIFICATION AND CHARACTERIZATION OF INVERTASE FROM YEAST

被引：40

作者：

LEGLER, G ^{[1
]}

KORTH, A ^{[1
]}

BERGER, A ^{[1
]}

EKHART, C ^{[1
]}

GRADNIG, G ^{[1
]}

STUTZ, AE ^{[1
]}

机构：

[1] GRAZ TECH UNIV,INST ORGAN CHEM,A-8010 GRAZ,AUSTRIA

来源：

CARBOHYDRATE RESEARCH | 1993年 / 250卷 / 01期

关键词：

D O I：

10.1016/0008-6215(93)84155-Y

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：

Glucose isomerase (EC 5.3.1.5) catalyzes the quantitative isomerisation of 5-azido-5-deoxy-D-gluco-(7) and -L-idofuranose (9), respectively, into the corresponding ketoses, 5-azido-5-deoxy-D-fructo-pyranose (8) and -L-sorbopyranose (10), respectively. Upon catalytic hydrogenation over palladium-on-charcoal, the fructose derivative 8 gives the natural product and the efficient glycosidase inhibitor 2,5-dideoxy-2,5-imino-D-mannitol (4), while the sorbose derivative 10 affords 2,5-dideoxy-2,5-dideoxy-2,5-imino-D-glucitol (5). This represents a preparatively very simple and efficient two-step synthesis of these biologically active compounds. Both are strong inhibitors of alpha- and beta-glucosidases from various sources, the D-manno-isomer 4 being distinctly more active. Because of its structural relationship with beta-D-fructofuranose, compound 4 is also a very good inhibitor of invertase from yeast and, as such, was for the first time employed, after immobilization on aminohexyl-sepharose, for the purification of this enzyme.

引用

页码：67 / 77

页数：11

共 61 条

[1] 5-DEOXY-5-FLUORO-D-GLUCOFURANOSE AND GLUCOFURANOSE-L-IDOFURANOSE SYNTHESIS AND NMR-STUDIES [J].