“Reverse” Carbocyclic Fleximers: Synthesis of a New Class of Adenosine Deaminase Inhibitors
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Citation of Original Publication
Zimmermann, Sarah C., Joshua M. Sadler, Peter I. O’Daniel, Nathaniel T. Kim, and Katherine L. Seley-Radtke. “‘Reverse’ Carbocyclic Fleximers: Synthesis of a New Class of Adenosine Deaminase Inhibitors.” Nucleosides, Nucleotides & Nucleic Acids 32, no. 3 (January 1, 2013): 137–54. https://doi.org/10.1080/15257770.2013.771187.
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This is an Accepted Manuscript of an article published by Taylor & Francis in Nucleosides, Nucleotides & Nucleic Acids on 2013-03-08, available online: https://www.tandfonline.com/doi/full/10.1080/15257770.2013.771187.
Abstract
A series of flexible carbocyclic pyrimidine nucleosides has been designed and synthesized. In contrast to previously reported “fleximers” from our laboratory, these analogues have the connectivity of the heterocyclic base system “reversed”, where the pyrimidine ring is attached to the sugar moiety, rather than the five membered imidazole ring. As was previously seen with the ribose fleximers, their inherent flexibility should allow them to adjust to enzyme binding site mutations, as well as increase the affinity for atypical enzymes. Preliminary biological screening has revealed surprising inhibition of adenosine deaminase, despite their lack of resemblance to adenosine.