Conformational and Orientational Switching of Uridine Derivatives by Borates
We have demonstrated for the first time that the syn-anti orientation of 5′-amino-5′-deoxyuridine (1b) can readily be switched by adding borate as an extermal controlling factor. In borate added phosphate buffer, the syn/anti ratio of 1b dramatically increased with increasing borate concentration. This unique syn preference is most probably driven by the cooperative action of cyclic esterification of the 1b's 2′,3′-cis-diol with borate and of hydrogen-bonding formation between 2-carbonyl oxygen and 5′-amino proton.
- Chemistry letters
Chemistry letters 1998(10), 1025-1026, 1998-10-05
The Chemical Society of Japan