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

Authors

Ahmed Khalil, Zagazig University, Ohio State University
Keisuke Ishita, Ohio State University
Tehane Ali, Ohio State University
Rohit Tiwari, Ohio State University, University of Notre Dame Australia
Ramy Riachy, Ohio State University
Antonio Toppino, Ohio State University, University of Torino
Sherifa Hasabelnaby, Ohio State University, Helwan University
Naum Sayfullin, Ohio State University
Allen G. Oliver, University of Notre Dame Australia
Judith C. Gallucci, Ohio State University
Zhenguo Huang, Ohio State UniversityFollow
Werner Tjarks, Ohio State University

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.