STUDIES ON WATER-SOLUBLE ARTIFICIAL RECEPTORS CONTAINING CHIRAL SIDE-CHAINS DERIVED FROM CARBOHYDRATES - 1 - SYNTHESIS OF OPTICALLY-ACTIVE CYCLOPHANE TCP44 AND ITS COMPLEXATION SELECTIVITY FOR AROMATIC GUESTS IN ACIDIC AQUEOUS-SOLUTIONS

Authors
TAKAHASHI I HIRANO Y ARAKAWA H KITAJIMA H HATANAKA M ISA K ODASHIMA K KOGA K
Citation
I. Takahashi et al., STUDIES ON WATER-SOLUBLE ARTIFICIAL RECEPTORS CONTAINING CHIRAL SIDE-CHAINS DERIVED FROM CARBOHYDRATES - 1 - SYNTHESIS OF OPTICALLY-ACTIVE CYCLOPHANE TCP44 AND ITS COMPLEXATION SELECTIVITY FOR AROMATIC GUESTS IN ACIDIC AQUEOUS-SOLUTIONS, Heterocycles, 46, 1997, pp. 589-603
Citations number
59
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
46
Year of publication
1997
Pages
589 - 603
Database
ISI
SICI code
0385-5414(1997)46:<589:SOWARC>2.0.ZU;2-5
Abstract
The details of the synthesis and complexation properties of L-tartrate -derived cyclophane (TCP44), the first totally synthetic host with a c hiral hydrophobic cavity, are described. The synthesis employs 1:1 cyc lization via a U-shaped precursor containing chiral C-4 units derived from L-tartaric acid. TCP44, soluble in acidic water as an amine salt, displayed a complexation selectivity for hydrophobic aromatic guests. Inclusion of aromatic guests into the cavity was verified by fluoresc ence and H-1 NMR spectra. A possible structure of inclusion cavity is discussed.