CHEMOENZYMATIC SYNTHESIS OF HOMOAZASUGARS

被引：29

作者：

HENDERSON, I ^{[1
]}

LASLO, K ^{[1
]}

WONG, CH ^{[1
]}

机构：

[1] Scripps Res Inst, DEPT CHEM, LA JOLLA, CA 92037 USA

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 03期

关键词：

D O I：

10.1016/0040-4039(94)85053-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chemoenzymatic approach for the synthesis of homoazasugars is described, utilizing an aldolase to catalyze the key asymmetric aldol addition reaction. This approach is illustrated by the synthesis of beta-D-homomannonojirimycin (11) using D-fructose diphosphate (FDP) aldolase.

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页码：359 / 362

页数：4

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共 7 条

[1] A FACILE, PRACTICAL SYNTHESIS OF 2,6-DIDEOXY-2,6-IMINO-7-O-BETA-D-GLUCOPYRANOSYL-D-GLYCERO-L-GULO-HEPTITOL (MDL 25,637) [J].

ANZEVENO, PB ;

CREEMER, LJ ;

DANIEL, JK ;

KING, CHR ;

LIU, PS .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (11) :2539-2542

[2] IMINOHEPTITOLS AS GLYCOSIDASE INHIBITORS - SYNTHESIS OF, AND MANNOSIDASE AND FUCOSIDASE INHIBITION BY, ALPHA-HOMOMANNOJIRMYCIN AND 6-EPI-HOMOMANNOJIRMYCIN [J].

BRUCE, I ;

FLEET, GWJ ;

DIBELLO, IC ;

WINCHESTER, B .

TETRAHEDRON LETTERS, 1989, 30 (51) :7257-7260

[3] IMINOHEPTITOLS AS GLYCOSIDASE INHIBITORS - SYNTHESIS OF AND SPECIFIC ALPHA-L-FUCOSIDASE INHIBITION BY BETA-L-HOMOFUCONOJIRIMYCIN AND 1-BETA-C-SUBSTITUTED DEOXYMANNOJIRIMYCINS [J].

FLEET, GWJ ;

NAMGOONG, SK ;

BARKER, C ;

BAINES, S ;

JACOB, GS ;

WINCHESTER, B .

TETRAHEDRON LETTERS, 1989, 30 (33) :4439-4442

[4] ALPHA-HOMONOJIRIMYCIN [2,6-DIDEOXY-2,6-IMINO-D-GLYCERO-L-GULO-HEPTITOL] FROM OMPHALEA-DIANDRA L - ISOLATION AND GLUCOSIDASE INHIBITION [J].

KITE, GC ;

FELLOWS, LE ;

FLEET, GWJ ;

LIU, PS ;

SCOFIELD, AM ;

SMITH, NG .

TETRAHEDRON LETTERS, 1988, 29 (49) :6483-6486

[5] USE OF DIHYDROXYACETONE PHOSPHATE DEPENDENT ALDOLASES IN THE SYNTHESIS OF DEOXYAZASUGARS [J].

LIU, KKC ;

KAJIMOTO, T ;

CHEN, LR ;

ZHONG, ZY ;

ICHIKAWA, Y ;

WONG, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (22) :6280-6289

[6] ENZYME-CATALYZED ORGANIC-SYNTHESIS - PRACTICAL ROUTES TO AZA SUGARS AND THEIR ANALOGS FOR USE AS GLYCOPROCESSING INHIBITORS [J].

LOOK, GC ;

FOTSCH, CH ;

WONG, CH .

ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (04) :182-190

[7] AMINO-SUGAR GLYCOSIDASE INHIBITORS - VERSATILE TOOLS FOR GLYCOBIOLOGISTS [J].

WINCHESTER, B ;

FLEET, GWJ .

GLYCOBIOLOGY, 1992, 2 (03) :199-210