A vector-selective reaction enables efficient construction of specific topology upon the primary side of beta-cyclodextrin.
N-dansylcysteines attached on the primary side of beta-cyclodextrin reacted with the saccharide hydroxyl groups in a vector-selective manner, affording the corresponding lactones. The desired topology of the lactones can be efficiently constructed simply by the selection of the proper enantiomer of D/L-cysteines. In comparison with the exo-lactone, the endo-lactone displayed 4 times stronger fluorescence intensity, stronger binding affinity to sodium adamantanecarboxylate, and 15 times larger signal changes in fluorescence intensity upon binding.
Yuan
De-Qi
DQ
Department of Molecular Medicinal Sciences, Graduate School of Biomedical Sciences, Nagasaki University, Nagasaki 852-8521, Japan. deqiyuan@.nagasaki-u.ac.jp
Kitagawa
Yumika
Y
Fukudome
Makoto
M
Fujita
Kahee
K
D007783:Lactones / Q000737:chemistry; D015394:Molecular Structure; D047392:beta-Cyclodextrins / Q000737:chemistry*
D007783:Lactones; D047392:beta-Cyclodextrins; C031215:betadex