SYNTHESIS OF 2,6-DIAMIDOPYRIDINE DERIVATIVES AND THEIR FUNCTIONS AS FLAVIN RECEPTORS IN CHLOROFORM

被引:44
作者
TAMURA, N [1 ]
MITSUI, K [1 ]
NABESHIMA, T [1 ]
YANO, Y [1 ]
机构
[1] GUNMA UNIV,DEPT CHEM,KIRYU,GUMMA 376,JAPAN
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1994年 / 10期
关键词
D O I
10.1039/p29940002229
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
It has been found that 2,6-diamidopyridine derivatives act as flavin receptors by a triple hydrogen bond towards a uracil moiety of an isoalloxazine ring in CHCl3. The association constants were determined by H-1 NMR (in CDCl3) and fluorescence (in CHCl3) spectroscopies; the largest is ca. 10(3) mol(-1) dm(3). The triple hydrogen bond toward C(2)=0, N(3)-H and C(4)=0 of the isoalloxazine ring was found to enhance slightly the oxidation activity in CHCl3.
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页码:2229 / 2237
页数:9
相关论文
共 45 条
[1]   FLAVIN-6-CARBOXYLIC ACIDS AS NOVEL AND SIMPLE FLAVOENZYME MODELS - NONENZYMATIC STABILIZATION OF THE FLAVIN SEMIQUINONE RADICAL AND THE 4A-HYDROPEROXYFLAVIN BY INTRAMOLECULAR HYDROGEN-BONDING [J].
AKIYAMA, T ;
SIMENO, F ;
MURAKAMI, M ;
YONEDA, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (17) :6613-6620
[2]  
BURNETT RM, 1974, J BIOL CHEM, V249, P4383
[3]  
CAGNIANT P, 1966, B SOC CHIM FR, P3249
[4]   HYDROGEN-BONDING AND MOLECULAR RECOGNITION - SYNTHETIC, COMPLEXATION, AND STRUCTURAL STUDIES ON BARBITURATE BINDING TO AN ARTIFICIAL RECEPTOR [J].
CHANG, SK ;
VANENGEN, D ;
FAN, E ;
HAMILTON, AD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (20) :7640-7645
[5]  
CRAM DJ, 1980, APPLICATIONS BIOCH 2, P815
[6]  
DANN O, 1954, LIEBIGS ANN CHEM, V589, P38
[7]   HPLC SEPARATION OF DNA ADDUCTS BASED ON HYDROGEN-BONDING [J].
FEIBUSH, B ;
SAHA, M ;
ONAN, K ;
KARGER, B ;
GIESE, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (24) :7531-7533
[8]   CHIRAL SEPARATION OF HETEROCYCLIC DRUGS BY HPLC - SOLUTE STATIONARY PHASE BASE-PAIR INTERACTIONS [J].
FEIBUSH, B ;
FIGUEROA, A ;
CHARLES, R ;
ONAN, KD ;
FEIBUSH, P ;
KARGER, BL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (12) :3310-3318
[9]  
Fendler J. H., 1982, MEMBRANE MIMETIC CHE
[10]   FLAVIN ANALOG METAL-ION COMPLEXES ACTING AS EFFICIENT PHOTOCATALYSTS IN THE OXIDATION OF PARA-METHYLBENZYL ALCOHOL BY OXYGEN UNDER IRRADIATION WITH VISIBLE-LIGHT [J].
FUKUZUMI, S ;
KURODA, S ;
TANAKA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (11) :3020-3027