SPECIFIC COMPLEXATION OF GLUCOSE WITH A DIPHENYLMETHANE-3,3'-DIBORONIC ACID-DERIVATIVE - CORRELATION BETWEEN THE ABSOLUTE-CONFIGURATION OF MONOSACCHARIDE AND DISACCHARIDE AND THE CIRCULAR DICHROIC ACTIVITY OF THE COMPLEX
被引:110
作者:
SHIOMI, Y
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机构:RES DEV CORP JAPAN,ERATO,CHEMIRECOGN PROJECT,AIKAWA 2432-3,KURUME,FUKUOKA 830,JAPAN
SHIOMI, Y
SAISHO, M
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机构:RES DEV CORP JAPAN,ERATO,CHEMIRECOGN PROJECT,AIKAWA 2432-3,KURUME,FUKUOKA 830,JAPAN
SAISHO, M
TSUKAGOSHI, K
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机构:RES DEV CORP JAPAN,ERATO,CHEMIRECOGN PROJECT,AIKAWA 2432-3,KURUME,FUKUOKA 830,JAPAN
TSUKAGOSHI, K
SHINKAI, S
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机构:RES DEV CORP JAPAN,ERATO,CHEMIRECOGN PROJECT,AIKAWA 2432-3,KURUME,FUKUOKA 830,JAPAN
SHINKAI, S
机构:
[1] RES DEV CORP JAPAN,ERATO,CHEMIRECOGN PROJECT,AIKAWA 2432-3,KURUME,FUKUOKA 830,JAPAN
[2] KYUSHU UNIV,FAC ENGN,DEPT ORGAN SYNTH,FUKUOKA 812,JAPAN
来源:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
|
1993年
/
17期
关键词:
D O I:
10.1039/p19930002111
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
For the development of receptor molecules that can precisely recognize sugar molecules, we recently synthesized bis-(6-methoxyphenyl)methane-3,3'-diboronic acid 2. This compound forms 1 : 1 complexes with mono- and di-saccharides and gives circular dichroism (CD) spectra specific to each saccharide. It was shown on the basis of H-1 NMR spectroscopy that the complex with D-glucose is a macrocyclic compound formed by the reaction of the two boronic acids with cis-1,2-diol and trans-4-OH, 5-CH2OH moieties. Thus, compound 2 becomes CD-active because of asymmetric immobilization of the two chromophoric benzene rings by ring closure with chiral saccharides. The association constants were in the following order: D-glucose (19000 dm3 mol-1) much greater than D-talose > D-galactose > D-mannose > D-fructose (= 0 dm3 mol-1) for monosaccharides, and D-maltose (100 dm3 mol-1) > D-cellobiose > D-lactose > D-saccharose (= 0 dm3 mol-1) for disaccharides. In particular, compound 2 showed a very high affinity toward D-glucose. D-Glucose gave a CD spectrum with positive exciton coupling whereas L-glucose gave a CD spectrum with negative exciton coupling. D-Galactose gave a CD spectrum with negative exciton coupling, whereas all other D-mono- and D-disaccharides tested herein gave CD spectra with positive exciton coupling. The results indicate that the absolute configuration of saccharides can be conveniently predicted from the sign and the strength of the CD spectra of their complex with compound 2. This means that the CD spectroscopic method using compound 2 as a receptor probe serves as a new sensory system for sugar molecules.