SYNTHESIS OF BETA-1-HOMONOJIRIMYCIN AND BETA-1-HOMOMANNOJIRIMYCIN USING THE ENZYME ALDOLASE

被引：40

作者：

HOLT, KE

LEEPER, FJ

HANDA, S

机构：

[1] UNIV CAMBRIDGE,CHEM LAB,CAMBRIDGE CB2 1EW,ENGLAND

[2] KINGS COLL LONDON,DEPT CHEM,LONDON WC2R 2LS,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 03期

关键词：

D O I：

10.1039/p19940000231

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The four stereoisomers of the four-carbon azido sugar 11 have been stereoselectively synthesised by a route involving Sharpless epoxidation and all are found to be substrates for rabbit muscle fructose 1,6-bisphosphate aldolase, giving tatter treatment with phosphatase) 6-azido-6-deoxyheptuloses 14; hydrogenation of 14a and 14b gave beta-1-homomannojirimycin 15a and beta-1-homonojirimycin 15b with high selectivity.

引用

页码：231 / 234

页数：4

共 24 条

[11] HIRAIZUMI S, 1993, J BIOL CHEM, V268, P9927
[12] PALLADIUM-MEDIATED STEREOCONTROLLED REDUCTIVE AMINATION OF AZIDO SUGARS PREPARED FROM ENZYMATIC ALDOL CONDENSATION - A GENERAL-APPROACH TO THE SYNTHESIS OF DEOXY AZA SUGARS
KAJIMOTO, T
CHEN, LR
LIU, KKC
WONG, CH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (17) : 6678 - 6680
[13] ALPHA-HOMONOJIRIMYCIN AND 2,5-DIHYDROXYMETHYL-3,4-DIHYDROXY-PYRROLIDINE - ALKALOIDAL GLYCOSIDASE INHIBITORS IN THE MOTH URANIA-FULGENS
KITE, GC
HORN, JM
ROMEO, JT
FELLOWS, LE
LEES, DC
SCOFIELD, AM
SMITH, NG
[J]. PHYTOCHEMISTRY, 1990, 29 (01) : 103 - 105
[14] ALPHA-HOMONOJIRIMYCIN [2,6-DIDEOXY-2,6-IMINO-D-GLYCERO-L-GULO-HEPTITOL] FROM OMPHALEA-DIANDRA L - ISOLATION AND GLUCOSIDASE INHIBITION
KITE, GC
FELLOWS, LE
FLEET, GWJ
LIU, PS
SCOFIELD, AM
SMITH, NG
[J]. TETRAHEDRON LETTERS, 1988, 29 (49) : 6483 - 6486
[15] BASIC MONOSACCHARIDE DERIVATIVES - TOOLS FOR EXPLORING THE ACTIVE-SITE OF GLYCOHYDROLASES AND FOR STUDIES IN GLYCOPROTEIN-BIOSYNTHESIS
LEGLER, G
[J]. PURE AND APPLIED CHEMISTRY, 1987, 59 (11) : 1457 - 1464
[16] A NEW CLASS OF ENDOGLYCOSIDASE INHIBITORS - STUDIES ON ENDOCELLULASES
LIOTTA, LJ
BERNOTAS, RC
WILSON, DB
GANEM, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (02) : 783 - 785
[17] FRUCTOSE 1,6-DIPHOSPHATE ALDOLASE-CATALYZED STEREOSELECTIVE C-C BOND FORMATION
LIU, KKC
PEDERSON, RL
WONG, CH
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (11): : 2669 - 2673
[18] TOTAL SYNTHESIS OF 2,6-DIDEOXY-2,6-IMINO-7-O-BETA-D-GLUCOPYRANOSYL-D-GLYCERO-L-GULO-HEPTITOL HYDROCHLORIDE - A POTENT INHIBITOR OF ALPHA-GLUCOSIDASES
LIU, PS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (21) : 4717 - 4721
[19] ENZYME-CATALYZED ORGANIC-SYNTHESIS - PRACTICAL ROUTES TO AZA SUGARS AND THEIR ANALOGS FOR USE AS GLYCOPROCESSING INHIBITORS
LOOK, GC
FOTSCH, CH
WONG, CH
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (04) : 182 - 190
[20] PATWARDHAN SA, 1974, SYNTHESIS-STUTTGART, P348

← 1 2 3 →