Conformational and orientational switching of uridine derivatives by borates

Takehiko Wada, Narutoshi Minamimoto, Yoshiaki Inaki, Yoshihisa Inoue

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)


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 external controlling factor. In borate added phosphate buffer, the synlanti 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.

Original languageEnglish
Pages (from-to)1025-1026
Number of pages2
JournalChemistry Letters
Issue number10
Publication statusPublished - 1998


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