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Titolo:
MOLECULAR RECOGNITION OF BETA-RIBOFURANOSIDES BY SYNTHETIC POLYPYRIDINE-MACROCYCLIC RECEPTORS
Autore:
INOUYE M; MIYAKE T; FURUSYO M; NAKAZUMI H;
Indirizzi:
UNIV OSAKA PREFECTURE,DEPT APPL MAT SCI SAKAI OSAKA 593 JAPAN
Titolo Testata:
Journal of the American Chemical Society
fascicolo: 50, volume: 117, anno: 1995,
pagine: 12416 - 12425
SICI:
0002-7863(1995)117:50<12416:MROBBS>2.0.ZU;2-A
Fonte:
ISI
Lingua:
ENG
Soggetto:
NUCLEOTIDE BASE RECOGNITION; HYDROGEN-BONDING INTERACTION; RESORCINOL CYCLIC TETRAMER; ARTIFICIAL RECEPTORS; POLYHYDROXY MACROCYCLE; SELECTIVE BINDING; ABSOLUTE-CONFIGURATION; INDUCED ISOMERIZATION; STACKING INTERACTIONS; CONVENIENT SYNTHESIS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
65
Recensione:
Indirizzi per estratti:
Citazione:
M. Inouye et al., "MOLECULAR RECOGNITION OF BETA-RIBOFURANOSIDES BY SYNTHETIC POLYPYRIDINE-MACROCYCLIC RECEPTORS", Journal of the American Chemical Society, 117(50), 1995, pp. 12416-12425

Abstract

Artificial ribofuranoside receptors were designed and synthesized. The design of the polypyridine-macrocyclic receptors was based on the multipoint hydrogen bond complementarity between the receptors and methyl beta-D-ribofuranoside. The binding affinity of the receptors for theribofuranoside in CDCl3 was very high (up to K-a = 5.2 x 10(3) M(-1)), so that even native ribose was extracted by them into such nonpolar solvents. Selective extraction of ribose by the receptors\was observed: the extractabilities, or affinities to the receptors of various pentoses and hexoses decreased in the following order: ribose > deoxyribose congruent to lxyose congruent to xylose > fructose > arabinose > glucose congruent to mannose congruent to galactose. The selectivity is governed by the OH direction and the whole size of the sugars as well as their shapes. Furthermore, fluorescence emission of the receptors was largely enhanced in the presence of methyl beta-D-ribofuranoside or ribose, and the degree for the fluorescence enhancement by the addition of various sugars was almost compatible with that of the extractabilities. The polypyridine-macrocycles represent rationally designed multifunctional artificial receptors for ribofuranosides.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 23/09/20 alle ore 14:20:09