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

[1] POLYMERIZATION OF 1,6-ANHYDRO-2,3,5-TRI-O-BENZYL ALPHA-D-GALACTOFURANOSE
LIN, JWP
SCHUERCH, C
MACROMOLECULES, 1972, 5 (05) : 656 - &
[2] An improved synthesis of 1,6-anhydro-2,3-di-O-benzyl-beta-D-xylo-hexopyranos-4-ulose
Caron, S
McDonald, AI
Heathcock, CH
CARBOHYDRATE RESEARCH, 1996, 281 (01) : 179 - 182
[3] 1,6-anhydro-2,3-di-O-benzyl-5C-[(R)-ethoxycarbonyl(hydroxy)methyl]-β-L-altrofuranose
Taillefumier, C
Charron, C
Chapleur, Y
Aubry, A
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2000, 56 (09): : 1168 - 1169
[4] SYNTHESIS OF 1,6-ANHYDRO-2,3-DIDEOXY-BETA-D-ERYTHRO-HEX-2-ENOPYRANOSE AND 1,6-ANHYDRO-2,3-DIDEOXY-BETA-D-THREO-HEX-2-ENOPYRANOSE FROM 3,4-DI-O-SUBSTITUTED GLYCALS BY A FACILE INTRAMOLECULAR FERRIER REACTION
MEREYALA, HB
VENKATARAMANAIAH, KC
DALVOY, VS
CARBOHYDRATE RESEARCH, 1992, 225 (01) : 151 - 153
[5] STUDY　ON　THE　SYNTHESIS，　RING－OPENING　REACTION　AND　GLYCOSIDATION　OF　1，6－ANHYDRO－2，4－DI－O－BENZYL－β－D－GLUCOPYRANOSE
Hong LIANG
Chang Pei FEI(Institute of Chemistry. Academia Sinica. Beijing 100080)
Chinese Chemical Letters, 1994, (08) : 655 - 658
[6] Study on the synthesis, ring-opening reaction and glycosidation of 1,6-anhydro-2,4-di-O-benzyl-beta-D-glucopyranose
Liang, H
Fei, CP
ACTA CHIMICA SINICA, 1996, 54 (02) : 198 - 205
[7] RING-OPENING POLYMERIZATION OF 1,6-ANHYDRO-2,4-DI-O-BENZYL-3-O-TERT-BUTYLDIMETHYLSILYL-BETA-D-GLUCOPYRANOSE AND SYNTHESIS OF ALPHA-(1-]3)-BRANCHED DEXTRANS
URYU, T
YAMANAKA, M
HENMI, M
HATANAKA, K
MATSUZAKI, K
CARBOHYDRATE RESEARCH, 1986, 157 : 157 - 169
[8] 1,6-ANHYDROFURANOSES .20. SYNTHESIS OF 2 1,6-2,3-DIANHYDROHEXOFURANOSES BY PAYNE OXIDATION OF 1,6-ANHYDRO-5-O-BENZOYL-2,3-DIDESOXY-BETA-D-ERYTHRO-HEX-2-ENOFURANOSE AND 1,6-ANHYDRO-5-O-BENZOYL-2,3-DIDESOXY-ALPHA-L-THREO-HEX-2-ENOFURANOSE
KOLL, P
EISERMANN, D
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1988, 7 (04) : 757 - 771
[9] X-RAY-DIFFRACTION STRUCTURAL-ANALYSIS OF 1,6-ANHYDRO-2-DEOXY-2,4-DI-C-METHYL-3-O-BENZYL-5-O-MESYL-ALPHA-L-IDOFURANOSE AND 1,6-ANHYDRO-2-DEXOSY-2,4-DI-C-METHYL-3,4-DI-O-BENZYL-BETA-D-GLUCOPYRANOSE
VORONTSOVA, LG
DEKAPRILEVICH, MO
CHIZHOV, OS
BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1985, 34 (07): : 1434 - 1439
[10] AMMONOLYSIS OF 1,6-ANHYDRO-2,4-DI-O-P-TOLYSULFONYL-BETA-D-GLUCOPYRANOSE AND SYNTHESIS OF 2,4-DIAMINO-2,4-DIDEOXY-D-GLUCOSE
JEANLOZ, RW
RAPIN, AMC
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (11): : 2978 - &

← 1 2 3 4 5 →