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

[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)
ANZEVENO, PB
CREEMER, LJ
DANIEL, JK
KING, CHR
LIU, PS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (11) : 2539 - 2542
[2] TOTAL SYNTHESIS OF (+)-ALPHA-HOMONOJIRIMYCIN
AOYAGI, S
FUJIMAKI, S
KIBAYASHI, C
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (20) : 1457 - 1459
[3] RABBIT MUSCLE ALDOLASE AS A CATALYST IN ORGANIC-SYNTHESIS
BEDNARSKI, MD
SIMON, ES
BISCHOFBERGER, N
FESSNER, WD
KIM, MJ
LEES, W
SAITO, T
WALDMANN, H
WHITESIDES, GM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (02) : 627 - 635
[4] SELECTIVE TRANSFORMATIONS OF 2,3-EPOXY ALCOHOLS AND RELATED DERIVATIVES - STRATEGIES FOR NUCLEOPHILIC-ATTACK AT CARBON-3 OR CARBON-2
BEHRENS, CH
SHARPLESS, KB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) : 5696 - 5704
[5] IMINOHEPTITOLS AS GLYCOSIDASE INHIBITORS - SYNTHESIS OF ALPHA-HOMOMANNOJIRIMYCIN, 6-EPI-ALPHA-HOMOMANNOJIRIMYCIN AND OF A HIGHLY SUBSTITUTED PIPECOLIC ACID
BRUCE, I
FLEET, GWJ
DIBELLO, IC
WINCHESTER, B
[J]. TETRAHEDRON, 1992, 48 (46) : 10191 - 10200
[6] IMINOHEPTITOLS AS GLYCOSIDASE INHIBITORS - SYNTHESIS OF, AND MANNOSIDASE AND FUCOSIDASE INHIBITION BY, ALPHA-HOMOMANNOJIRMYCIN AND 6-EPI-HOMOMANNOJIRMYCIN
BRUCE, I
FLEET, GWJ
DIBELLO, IC
WINCHESTER, B
[J]. TETRAHEDRON LETTERS, 1989, 30 (51) : 7257 - 7260
[7] A NOVEL CONVENIENT PREPARATION OF DIHYDROXYACETONE PHOSPHATE AND ITS USE IN ENZYMATIC ALDOL REACTIONS
EFFENBERGER, F
STRAUB, A
[J]. TETRAHEDRON LETTERS, 1987, 28 (15) : 1641 - 1644
[8] IMINOHEPTITOLS AS GLYCOSIDASE INHIBITORS - SYNTHESIS OF AND SPECIFIC ALPHA-L-FUCOSIDASE INHIBITION BY BETA-L-HOMOFUCONOJIRIMYCIN AND 1-BETA-C-SUBSTITUTED DEOXYMANNOJIRIMYCINS
FLEET, GWJ
NAMGOONG, SK
BARKER, C
BAINES, S
JACOB, GS
WINCHESTER, B
[J]. TETRAHEDRON LETTERS, 1989, 30 (33) : 4439 - 4442
[9] INHIBITION OF HIV REPLICATION BY AMINO-SUGAR DERIVATIVES
FLEET, GWJ
KARPAS, A
DWEK, RA
FELLOWS, LE
TYMS, AS
PETURSSON, S
NAMGOONG, SK
RAMSDEN, NG
SMITH, PW
SON, JC
WILSON, F
WITTY, DR
JACOB, GS
RADEMACHER, TW
[J]. FEBS LETTERS, 1988, 237 (1-2) : 128 - 132
[10] Griffith W. P., 1990, ALDRICHIM ACTA, V23, P13

← 1 2 3 →