SYNTHESIS, METAL-BINDING PROPERTIES AND POLYPEPTIDE SOLUBILIZATION OF CROWNED ARBOROLS

被引:81
作者
NAGASAKI, T [1 ]
KIMURA, O [1 ]
UKON, M [1 ]
HAMACHI, I [1 ]
SHINKAI, S [1 ]
ARIMORI, S [1 ]
机构
[1] KYUSHU UNIV,FAC ENGN,DEPT ORGAN SYNTH,FUKUOKA 812,JAPAN
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 01期
关键词
D O I
10.1039/p19940000075
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first dendritic crown ether polymers ('crowned' arborols: G1, G2 and G3) have been synthesized and characterized. The convergent synthetic method was found to be more convenient than the divergent synthetic method. The building block in the branch was prepared from N-benzyloxycarbonyl-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane and 3,5-bis(ethoxycarbonyl-methoxy)benzoyl chloride. Since the basic repeating unit is the amino dicarboxylic acid, one can utilize the methods developed for peptide synthesis. Final products were obtained in moderate yields by coupling of each generational fragment with a core (benzene-1,3,5-tricarbonyl trichloride) followed by reduction of all amide linkages to tertiary amine linkages by borane-dimethyl sulfide. The complexation ability of these 'crowned' arborols was estimated by two-phase solvent extraction of alkali picrate salts. We found that some of these arborols can solubilize proteins in organic solvents.
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收藏
页码:75 / 81
页数:7
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