Novel porphyrin-cryptand cyclic systems:: Receptors for saccharide recognition in water

被引:71
作者
Král, V
Rusin, O
Schmidtchen, FP
机构
[1] Inst Chem Technol, Dept Analyt Chem, CR-16628 Prague, Czech Republic
[2] Tech Univ Munich, Dept Organ Chem & Biochem, D-85747 Garching, Germany
关键词
D O I
10.1021/ol007069w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Two macrocyclic porphyrin sandwich systems, 4 and 5, together with the linear compound 6 have been prepared and examined as saccharide receptors, The cyclic porphyrin-cryptand conjugates 4 and 5 bind saccharides efficiently in highly competitive media with a preference for trisaccharides probably due to a complementary topology of hydrophobic and hydrophilic solvating regimes with respect to the sugar guests.
引用
收藏
页码:873 / 876
页数:4
相关论文
共 17 条
[1]   Molecular delivery systems using macrocyclic sugar clusters [J].
Aoyama, Y ;
Matsuda, Y ;
Chuleeraruk, J ;
Nishiyama, K ;
Fujimoto, K ;
Fujimoto, T ;
Shimizu, T ;
Hayashida, O .
PURE AND APPLIED CHEMISTRY, 1998, 70 (12) :2379-2384
[2]  
Bähr A, 2000, HELV CHIM ACTA, V83, P1346, DOI 10.1002/1522-2675(20000705)83:7<1346::AID-HLCA1346>3.0.CO
[3]  
2-3
[5]   PHARMACEUTICS AND DRUG DELIVERY ASPECTS OF HEME AND PORPHYRIN THERAPY [J].
CANNON, JB .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1993, 82 (05) :435-446
[6]   MOLECULAR CATALYSTS FOR MULTIELECTRON REDOX REACTIONS OF SMALL MOLECULES - THE COFACIAL METALLODIPORPHYRIN APPROACH [J].
COLLMAN, JP ;
WAGENKNECHT, PS ;
HUTCHISON, JE .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (15-16) :1537-1554
[7]  
Davis AP, 1999, ANGEW CHEM INT EDIT, V38, P2978
[8]   Saccharide-directed cell recognition and molecular delivery using macrocyclic saccharide clusters: Masking of hydrophobicity to enhance the saccharide specificity [J].
Fujimoto, K ;
Miyata, T ;
Aoyama, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (14) :3558-3559
[9]   SYNTHESIS AND CHARACTERIZATION OF THE 1ST WATER-SOLUBLE CLOSELY INTERSPACED COFACIAL PORPHYRIN DIMER [J].
KARAMAN, R ;
BRUICE, TC .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (11) :3470-3472
[10]   Porphyrin-polyazacryptand conjugates:: Novel receptors for nucleotides [J].
Král, V ;
Cattani, A ;
Sinica, A ;
Schmidtchen, FP .
TETRAHEDRON, 1999, 55 (25) :7829-7834