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Potassium fluoride for the promotion of β‐cyclodextrin‐induced regioselective PO(3′) cleavage of adenosine 2′, 3′‐cyclic phosphate
Author(s) -
Sawata Shinya,
Komiyama Makoto
Publication year - 1992
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610050812
Subject(s) - chemistry , regioselectivity , phosphate , adenosine , cleavage (geology) , medicinal chemistry , cyclodextrin , fluoride , potassium fluoride , stereochemistry , potassium phosphate , inorganic chemistry , organic chemistry , catalysis , biochemistry , geotechnical engineering , fracture (geology) , engineering
Both the regioselectivity and the reaction rate for the β‐cyclodextrin (β‐CyD)‐induced P–O(3′) cleavage of adenosine 2′, 3′‐cyclic phosphate (A > p) to adenosine 2′‐phosphate are greatly promoted by KF. The promoting activity of KF is much larger than that of KCl. KF amplifies the difference in the chemical circumstance between the P–O(2′) and the P–O(3′) bonds of A > p, induced by β‐CyD on complex formation with A > p. The higher activity of KF is ascribed to absence of complex formation of F − ion with β‐CyD, which results in deeper penetration of A > p into the cavity of β‐CyD.