Conformational and Orientational Switching of Uridine Derivatives by Borates
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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