SEMISYNTHESIS OF A.23187 (CALCIMYCIN) ANALOGS WITH 5-N-AMINO SUBSTITUENTS - THEIR COMPLEXATION OF CALCIUM AND MAGNESIUM

被引:8
作者
SAMIH, F [1 ]
PRUDHOMME, M [1 ]
DAUPHIN, G [1 ]
JEMINET, G [1 ]
机构
[1] UNIV CLERMONT FERRAND, CHIM ORGAN BIOL LAB, CNRS, URA 485, F-63177 CLERMONT FERRAND, FRANCE
关键词
D O I
10.1016/S0040-4020(01)87824-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The semi-synthesis of A.23187 (calcimycin) analogs 14̃ bearing the respective substituents : 5-NH2, 5-NHCH3, 5-N(CH3)2, 5-NHCOCH3 was carried out. The complexing properties of 14̃ for calcium and magnesium were determined by two-phase experiments (water/toluene-butanol 70:30 W/W) and found to be much weaker than these of A.23187 or X.14885A. There was a discrepancy with theoretical predictions made from model carboxybenzoxazoles. © 1990.
引用
收藏
页码:5177 / 5186
页数:10
相关论文
共 20 条
[1]   X-14885A - AN IONOPHORE CLOSELY RELATED TO CALCIMYCIN (A-23187) - NMR, THERMODYNAMIC, AND KINETIC-STUDIES OF CATION SELECTIVITY [J].
ALBRECHTGARY, AM ;
BLANCPARASOTE, S ;
BOYD, DW ;
DAUPHIN, G ;
JEMINET, G ;
JUILLARD, J ;
PRUDHOMME, M ;
TISSIER, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (23) :8598-8609
[2]   CRYSTALLINE-STRUCTURE OF THE MAGNESIUM COMPLEX OF CALCIMYCINE (A.23187) [J].
ALLEAUME, M ;
BARRANS, Y .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1985, 63 (12) :3482-3485
[3]   COMPARATIVE STUDIES OF 3 IONOPHORE ANTIBIOTICS - X.537A (LASALOCIDE), A.23187 (CALCIMYCIDE) AND X.14547A - COMPLEXATION OF IA AND IIA CATIONS AND CA++ TRANSPORT [J].
BOLTE, J ;
DEMUYNCK, C ;
JEMINET, G ;
JUILLARD, J ;
TISSIER, C .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1982, 60 (08) :981-989
[4]  
CASTRO B, 1975, TETRAHEDRON LETT, P1219
[5]   EQUILIBRIA BETWEEN IONOPHORE A23187 AND DIVALENT-CATIONS - STABILITY OF 1-1 COMPLEXES IN SOLUTIONS OF 80-PERCENT METHANOL WATER [J].
CHAPMAN, CJ ;
PURI, AK ;
TAYLOR, RW ;
PFEIFFER, DR .
BIOCHEMISTRY, 1987, 26 (16) :5009-5018
[6]   POLYETHER ANTIBIOTICS SYNTHESIS - TOTAL SYNTHESIS AND ABSOLUTE-CONFIGURATION OF THE IONOPHORE-A-23187 [J].
EVANS, DA ;
SACKS, CE ;
KLESCHICK, WA ;
TABER, TR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (22) :6789-6791
[7]  
GRELL E, 1984, PROGR BIOORGANIC CHE, P39
[8]  
GRESH N, 1986, NEW J CHEM, V10, P201
[9]  
HAMILL RL, 1972, 12TH INT C ANT AG CH
[10]  
HEBRANT M, 1989, THESIS U B PASCAL AU