SYNTHESIS OF 1,6-ANHYDRO-2,3-DI-O-FARNESYL-5-O-([(PHOSPHONOMETHYL)PHOSPHINYL]METHYL)-ALPHA-D-GALACTOFURANOSE - A ZARAGOZIC ACID - PRESQUALENE PYROPHOSPHATE HYBRID

被引：6

作者：

VALENTIJN, ARPM

BROXTERMAN, HJG

VANDERMAREL, GA

COHEN, LH

VANBOOM, JH

机构：

[1] LEIDEN UNIV,GORLAEUS LABS,LEIDEN INST CHEM,2300 RA LEIDEN,NETHERLANDS

[2] TNO PREVENT & HLTH,GAUBIUS LAB,2301 CE LEIDEN,NETHERLANDS

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 1995年 / 14卷 / 06期

关键词：

D O I：

10.1080/07328309508005373

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：

A multi-step synthesis of a new potential inhibitor (i.e., compound 2) of squalene synthase is described, starting from D-galactose. The title compound is a hybrid of presqualene pyrophopshate and the recently discovered zaragozic acids, which are picomolar competitive inhibitors of the enzyme squalene synthase.

引用

页码：737 / 749

页数：13

共 48 条

[21] CHEMICAL SYNTHESIS OF A NEW POLYSACCHARIDE - RING-OPENING POLYMERIZATION OF 1,6-ANHYDRO-2,3,4-TRI-O-BENZYL-BETA-D-ALLOPYRANOSE AND PREPARATION OF STEREOREGULAR (1-]6)-ALPHA-D-ALLOPYRANAN
URYU, T
SAKAMOTO, Y
HATANAKA, K
MATSUZAKI, K
MACROMOLECULES, 1984, 17 (07) : 1307 - 1312
[22] SYNTHESIS OF 2,3,4-TRI-O-BENZYL-[1-]6]-ALPHA-D-GLUCOPYRANAN AND [1-]6]-ALPHA-D-GLUCOPYRANAN WITH HIGH MOLECULAR-WEIGHT BY POLYMERIZATION OF 1,6-ANHYDRO-2,3,4-TRI-O-BENZYL-BETA-D-GLUCOPYRANOSE
URYU, T
TACHIKAWA, H
OHAKU, KI
TERUI, K
MATSUZAKI, K
MAKROMOLEKULARE CHEMIE-MACROMOLECULAR CHEMISTRY AND PHYSICS, 1977, 178 (07): : 1929 - 1940
[23] UNSATURATED SUGARS .1. DECARBOXYLATIVE ELIMINATION OF METHYL 2,3-DI-O-BENZYL-ALPHA-D-GLUCOPYRANOSIDURONIC ACID TO METHYL 2,3-DI-O-BENZYL-4-DEOXY-BETA-L-THREO-PENT-4-ENOPYRANOSIDE
PHILIPS, KD
ZEMLICKA, J
HORWITZ, JP
CARBOHYDRATE RESEARCH, 1973, 30 (02) : 281 - 286
[24] SYNTHESIS, CRYSTAL-STRUCTURE, AND CONFORMATION OF 3-O-(6-O-ACETYL-2,3-ANHYDRO-4-DEOXY-ALPHA-L-RIBO-HEXOPYRANOSYL)-1,2-5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE
KRAJEWSKI, JW
GLUZINSKI, P
URBANCZYKLIPKOWSKA, Z
BANASZEK, A
DOBLER, M
CARBOHYDRATE RESEARCH, 1984, 134 (01) : 11 - 22
[25] SYNTHETIC STUDIES ON PLANT-CELL WALL GLYCANS .1. SYNTHESIS OF METHYL (ALLYL 2,3-DI-O-BENZYL-BETA-D-GALACTOPYRANOSID)URONATE AND METHYL (2,3-DI-O-BENZYL-ALPHA-AND BETA-D-GALACTOPYRANOSYL FLUORIDE)URONATE
NAKAHARA, Y
OGAWA, T
CARBOHYDRATE RESEARCH, 1988, 173 (02) : 306 - 315
[26] SYNTHESIS OF D-XYLOSE, LABELED WITH TRITIUM IN 5-POSITION, AND ITS DERIVATIVES, 1,2,4-ORTHOACETYL-3-O-ACETYL-ALPHA-D-XYLOPYRANOSE-5-H-3 AND 1,5-ANHYDRO-2,3-DI-O-ACETYL-BETA-D-XYLOFURANOSE-5-H-3
BOCHKOV, AF
RODIONOV, AV
BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1975, 24 (03): : 590 - 593
[27] REACTION OF 1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE AND SOME OF ITS DERIVATIVES WITH DIAZOMETHANE-STANNOUS CHLORIDE - SYNTHESIS OF 3,5-DI-O-METHYL- AND 5-O-METHYL-D-GLUCOSE DERIVATIVES
CHITTENDEN, GJF
CARBOHYDRATE RESEARCH, 1979, 74 (SEP) : 333 - 336
[28] THE PHOTOCHEMISTRY OF CARBOHYDRATE-DERIVATIVES .5. SYNTHESIS OF METHYL 2,3-DI-O-(BETA-D-GLUCOPYRANOSYL)-ALPHA-L-FUCOPYRANOSIDE AND METHYL 2,3-DI-O-(BETA-D-GALACTOPYRANOSYL)-ALPHA-L-FUCOPYRANOSIDE USING PHOTOLABILE O-(2-NITROBENZYLIDENE) ACETALS AS TEMPORARY BLOCKING GROUPS
COLLINS, PM
MUNASINGHE, VRN
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (05): : 921 - 926
[29] SYNTHESIS OF N-[2-O-(2-ACETAMIDO-1-O-ACYL (OR 1,6-DI-O-ACYL)-2,3-DIDEOXY-ALPHA-D-GLUCOPYRANOSE-3-YL]-D-LACTOYL]-L-ALANYL-D-ISOGLUTAMINE METHYL-ESTERS, AND THEIR IMMUNOADJUVANT ACTIVITIES .33.
HASEGAWA, A
KIGAWA, K
KISO, M
AZUMA, I
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1986, 50 (08): : 2091 - 2094
[30] An efficient synthesis of methyl 1,3-O-isopropylidene-α-D-fructofuranoside and 2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal derivatives from sucrose
Hanaya, T
Sato, N
Yamamoto, H
CARBOHYDRATE RESEARCH, 2005, 340 (16) : 2494 - 2501

← 1 2 3 4 5 →