Title

Iodine monochloride facilitated deglycosylation, anomerization, and isomerization of 3-substituted thymidine analogues

RIS ID

106065

Publication Details

Khalil, A., Ishita, K., Ali, T., Tiwari, R., Riachy, R., Toppino, A., Hasabelnaby, S., Sayfullin, N., Oliver, A. G., Gallucci, J., Huang, Z. & Tjarks, W. (2014). Iodine monochloride facilitated deglycosylation, anomerization, and isomerization of 3-substituted thymidine analogues. Nucleosides, Nucleotides and Nucleic Acids: an international journal for rapid communication, 33 (12), 786-799.

Abstract

The reaction of thymidine, 3-mono-, and 3,3',5'-trialkylsubstitued thymidine analogues with iodine monochloride (ICl) was investigated. Treatment with ICl resulted in rapid deglycosylation, anomerization, and isomerization of thymidine and 3-substituted thymidine analogues under various reaction conditions leading to the formation of the nucleobases as the major products accompanied by minor formation of α-furanosidic-, α-pyranosidic-, and β-pyranosidic nucleosides. On the other hand, 3,3',5'-trisubstitued thymidine analogues were only deglycosylated and anomerized. These results are similar to those observed for the acidic hydrolysis of the glycoside bond in nucleosides, but were presumably caused by the Lewis acid character of an iodine electrophile.

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Link to publisher version (DOI)

http://dx.doi.org/10.1080/15257770.2014.945648