Synthetic applications of glucose isomerase:: isomerisation of C-5-modified (2R,3R,4R)-configured hexoses into the corresponding 2-ketoses

被引：19

作者：

Fechter, MH ^{[1
]}

Stütz, AE ^{[1
]}

机构：

[1] Graz Univ Technol, Inst Organ Chem, A-8010 Graz, Austria

来源：

CARBOHYDRATE RESEARCH | 1999年 / 319卷 / 1-4期

基金：

奥地利科学基金会;

关键词：

D-allofuranose; 2,5-dideoxy-2,5-iminoalditol; galactosidase inhibitor; glucose isomerase; L-tagatopyranose; D-psicopyranose;

D O I：

10.1016/S0008-6215(99)00119-6

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：

Immobilised glucose isomerase (EC 5.3.1.5) accepted various (2R,3R,4R)-configured hexoses such as 5-deoxy-D-ribo-hexose, 5-azido-5-deoxy-D-allose, as well as the corresponding epimer at C-5, 5-azido-5-deoxy-L-talose, as substrates. From the resulting azidodeoxyketoses, 5-azido-5-deoxy-D-psico- and -L-tagatopyranose, the powerful D-galactosidase inhibitors 2,5-dideoxy-2,5-imino-D-galactital and -D-altritol were obtained in one additional step. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：55 / 62

页数：8

共 29 条

[11]

DERAADT A, 1995, ADV DET R M, V4, P175

[12] ENZYMATIC ALDOL CONDENSATION ISOMERIZATION AS A ROUTE TO UNUSUAL SUGAR-DERIVATIVES [J].

DURRWACHTER, JR ;

DRUECKHAMMER, DG ;

NOZAKI, K ;

SWEERS, HM ;

WONG, CH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (24) :7812-7818

[13] ENZYMATIC ALDOL REACTION ISOMERIZATION AS A ROUTE TO UNUSUAL SUGARS [J].

DURRWACHTER, JR ;

SWEERS, HM ;

NOZAKI, K ;

WONG, CH .

TETRAHEDRON LETTERS, 1986, 27 (11) :1261-1264

[14] FRUCTOSE 1,6-DIPHOSPHATE ALDOLASE CATALYZED STEREOSELECTIVE SYNTHESIS OF C-ALKYL AND N-CONTAINING SUGARS - THERMODYNAMICALLY CONTROLLED C-C BOND FORMATIONS [J].

DURRWACHTER, JR ;

WONG, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (18) :4175-4181

[15] Glucose isomerase catalysed isomerisation reactions of (2R,3R)-configured aldofuranoses into the corresponding open-chain 2-ketoses [J].

Ebner, M ;

Stütz, AE .

CARBOHYDRATE RESEARCH, 1997, 305 (3-4) :331-336

[16]

Huwe CM, 1997, SYNTHESIS-STUTTGART, P61

[17] STEREOCONTROLLED SYNTHESIS OF 1,7A-DIEPIALEXINE [J].

IKOTA, N .

TETRAHEDRON LETTERS, 1992, 33 (18) :2553-2556

[18]

ITOKA N, 1993, HETEROCYCLES, P2035

[19] NEW SYNTHESIS OF 5-AMINO-5-DEOXY-1, 2-O-ISOPROPYLIDES-ALPHA-D-GLUCOFURANOSE [J].

KLEMER, A ;

HOFMEISTER, U ;

LEMMES, R .

CARBOHYDRATE RESEARCH, 1979, 68 (02) :391-395

[20] USE OF 5-DEOXY-RIBO-HEXOFURANOSE DERIVATIVES FOR THE PREPARATION OF 5'-NUCLEOTIDE PHOSPHONATES AND HOMORIBONUCLEOSIDES [J].

MIKHAILOV, SN ;

PADYUKOVA, NS ;

KARPEISKII, MY ;

KOLOBUSHKINA, LI ;

BEIGELMAN, LN .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1989, 54 (04) :1055-1066

← 1 2 3 →