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

[41] SYNTHESIS OF ALKYL 4,6-DI-O-ACETYL-2,3-DIDEOXY-ALPHA-D-THREO-HEX-2-ENOPYRANOSIDES FROM 3,4,6-TRI-O-ACETYL-1,5-ANHYDRO-2-DEOXY-D-LYXO-HEX-1-ENITOL (3,4,6-TRI-O-ACETYL-D-GALACTAL)
GRYNKIEWICZ, G
PRIEBE, W
ZAMOJSKI, A
CARBOHYDRATE RESEARCH, 1979, 68 (01) : 33 - 41
[42] SYNTHESIS OF METHYL 2,6-DIDEOXY-4-O-(TETRAHYDROPYRAN-2-YL)-ALPHA-L-ERYTHRO-HEXOPYRANOSID-3-ULOSE AND 5-DEOXY-2,3-O-ISOPROPYLIDENE-1-O-(TETRAHYDROPYRAN-2-YL)-BETA-D-THREO-HEX-5-ENULOPYRANOSE
KLEMER, A
BALKAU, D
JOURNAL OF CHEMICAL RESEARCH-S, 1978, (09): : 303 - &
[43] SYNTHETIC STUDIES IN CARBOHYDRATES .4. FACILE SYNTHESIS OF 2-METHYL-[3,4-DI-O-ACETYL-6-O-(CHLOROACETYL)-1,2-DIDEOXY-ALPHA-D-GLUCOPYRANO]-[2',1'=4,5]-2-OXAZOLINE
MATTA, KL
BARLOW, JJ
CARBOHYDRATE RESEARCH, 1976, 51 (02) : 215 - 222
[44] PHOSPHINITES OF CARBOHYDRATES AS CHIRAL LIGANDS FOR ASYMMETRIC SYNTHESIS CATALYZED BY COMPLEXES .1. HYDROGENATION OF AMINO-ACID PRECURSORS BY RHODIUM(I) CHELATES OF METHYL 4,6-O-BENZYLIDENE-2,3-BIS-O-(DIPHENYLPHOSPHINO)-ALPHA-D-GLUCOPYRANOSIDES
SELKE, R
REACTION KINETICS AND CATALYSIS LETTERS, 1979, 10 (02): : 135 - 138
[45] SYNTHETIC STUDIES IN CARBOHYDRATES .4. FACILE SYNTHESIS OF 2-METHYL-[4,6-DI-O-ACETYL-1,2-DIDEOXY-3-O-(2,3,4,6-TETRA-O-ACETYL-D-GLYCOPYRANOSYL)-ALPHA-D-GLUCOPYRANO]-[2',1',4,5]-2-OXAZOLINES, KEY INTERMEDIATES FOR SYNTHESIS OF OLIGOSACCHARIDES
MATTA, KL
BARLOW, JJ
CARBOHYDRATE RESEARCH, 1977, 53 (01) : 47 - 56
[46] CRYSTAL-STRUCTURES OF ANALOGS OF 3,1'-ANHYDRO NUCLEOSIDES .1. 3,1'-ANHYDRO-2-(4',6'-DI-O-ACETYL-2',3'-DIDEOXY-ALPHA-D-RIBO-HEXOPYRANOSE)-3-HYDROXY-5-METHYL-2H-1,2,6-THIADIAZINE-1,1-DIOXIDE (TDR)
FOCESFOCES, C
SMITHVERDIER, P
FLORENCIOSABATE, F
GARCIABLANCO, S
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1975, 31 (JAN15): : 140 - 144
[47] STUDIES IN OLIGOSACCHARIDE CHEMISTRY .6. SYNTHESIS OF A DISACCHARIDE OXAZOLINE - 2-METHYL-[4,6-DI-O-ACETYL-1,2-DIDEOXY-3-O-(2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSYL)-ALPHA-D-GLUCOPYRANO] [2',1'-4,5]-2-OXAZOLINE
AUGE, C
VEYRIERES, A
CARBOHYDRATE RESEARCH, 1976, 46 (02) : 293 - 298
[48] Chain extension of carbohydrates .6. Synthesis of the two C-6 epimers of the 6-acetylamino-4,6-dideoxyheptopyranosiduronic acid present in amipurimycin by means of stereocontrolled ethynylation of methyl 2,3-di-O-benzyl-4-deoxy-alpha-D-xylo-hexodialdo-1,5-pyranoside
Czernecki, S
Valery, JM
Wilkens, R
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1996, 69 (05) : 1347 - 1351

← 1 2 3 4 5 →