MOENOMYCIN-A - STRUCTURE ACTIVITY RELATIONS SYNTHESIS OF THE D-GALACTURONAMIDE ANALOG OF THE SMALLEST ANTIBIOTICALLY ACTIVE DEGRADATION PRODUCT OF MOENOMYCIN-A

被引:24
作者
MOLLER, U
HOBERT, K
DONNERSTAG, A
WAGNER, P
MULLER, D
FEHLHABER, HW
MARKUS, A
WELZEL, P
机构
[1] RUHR UNIV BOCHUM,FAK CHEM,POSTFACH 102148,W-4630 BOCHUM,GERMANY
[2] HOECHST AG,PHARMAFORSCH,W-6230 FRANKFURT 80,GERMANY
关键词
D O I
10.1016/S0040-4020(01)80351-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Compound 10c which is the galacturonamide analogue of 2, the smallest degradation product of moenomycin A (1) with full antibiotic activity, has been synthesized. 10c is devoid of antibiotic activity.
引用
收藏
页码:1635 / 1648
页数:14
相关论文
共 85 条
[1]   BIS(ALLYLOXY)(DIISOPROPYLAMINO)PHOSPHINE AS A NEW PHOSPHINYLATION REAGENT FOR THE PHOSPHORYLATION OF HYDROXY FUNCTIONS [J].
BANNWARTH, W ;
KUNG, E .
TETRAHEDRON LETTERS, 1989, 30 (32) :4219-4222
[2]   A SIMPLE AND EFFECTIVE CHEMICAL PHOSPHORYLATION PROCEDURE FOR BIOMOLECULES [J].
BANNWARTH, W ;
TRZECIAK, A .
HELVETICA CHIMICA ACTA, 1987, 70 (01) :175-186
[3]   ISOMERIZATION OF ALLYL ETHERS CATALYZED BY CATIONIC IRIDIUM COMPLEX [IR(CYCLO-OCTA-1,5-DIENE)(PMEPH2)2]PF6 - HIGHLY STEREOSELECTIVE ROUTE TO TRANS-PROPENYL ETHERS [J].
BAUDRY, D ;
EPHRITIKHINE, M ;
FELKIN, H .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (16) :694-695
[4]   NMR SPECTRAL STUDIES .12. TRICHLOROACETYL ISOCYANATE AS AN INSITU DERIVATIZING REAGENT FOR C-13 NMR-SPECTROSCOPY OF ALCOHOLS, PHENOLS AND AMINES [J].
BOSE, AK ;
SRINIVASAN, PR .
TETRAHEDRON, 1975, 31 (24) :3025-3029
[5]  
BOSS R, 1976, ANGEW CHEM INT EDIT, V15, P588
[6]  
BOSS R, 1976, ANGEW CHEM, V88, P578
[7]   THE USE OF N-ALKOXYCARBONYL DERIVATIVES OF 2-AMINO-2-DEOXY-D-GLUCOSE AS DONORS IN GLYCOSYLATION REACTIONS [J].
BOULLANGER, P ;
JOUINEAU, M ;
BOUAMMALI, B ;
LAFONT, D ;
DESCOTES, G .
CARBOHYDRATE RESEARCH, 1990, 202 :151-164
[8]   N-ALLYLOXYCARBONYL DERIVATIVES OF D-GLUCOSAMINE AS PROMOTERS OF 1,2-TRANS-GLUCOSYLATION IN KOENIGS-KNORR REACTIONS AND IN LEWIS ACID-CATALYZED CONDENSATIONS [J].
BOULLANGER, P ;
BANOUB, J ;
DESCOTES, G .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (06) :1343-1348
[9]   SELECTIVE CLEAVAGE OF ALLYL ETHERS UNDER MILD CONDITIONS BY TRANSITION-METAL REAGENTS [J].
COREY, EJ ;
SUGGS, JW .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (18) :3224-3224
[10]   SYNTHESIS OF TRIBUTYLSTANNYL ETHERS OF CARBOHYDRATES [J].
CROWE, AJ ;
SMITH, PJ .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1976, 110 (03) :C57-C59