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Diastereoisomer‐Selective Inclusion Complexation of Cinchona Alkaloids with a Modified β ‐Cyclodextrin: Fluorescent Behavior Enhanced by Chiral‐Tether Binding. Short Communication
Author(s) -
Liu Yu,
Yang YingWei,
Zhang HengYi,
Hu BoWen,
Ding Fei,
Li ChunJu
Publication year - 2004
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200490042
Subject(s) - chemistry , diastereomer , fluorescence , cyclodextrin , cinchona alkaloids , quinidine , titration , hydroxymethyl , aqueous solution , stereochemistry , combinatorial chemistry , organic chemistry , enantioselective synthesis , medicine , physics , quantum mechanics , pharmacology , catalysis
The molecular 1 : 1 complexation of cinchona alkaloids by mono(6‐deoxy‐6‐{[( R )‐1‐(hydroxymethyl)propyl]amino})‐ β ‐cyclodextrin ( 1 ) in aqueous solution has been investigated by 2D‐NMR, fluorescence titration, and fluorescence‐lifetime experiments. Generally, with 1 as the host, in contrast to β ‐cyclodextrin proper, strong binding of quinine ( 2 ; K a =84200 M −1 ) and quinidine ( 3 ; K a =27300 M −1 ) at pH 6.8 was observed, as monitored by an increase in fluorescence intensity, with a fair degree of diastereoisomer discrimination ( ca. 3 : 1). To rationalize these results, two possible cooperative complexation modes, including specific H‐bonding interactions to the chiral tether of the cyclodextrin portion, are proposed.