Backbone-Anchoring, Solid-Phase Synthesis Strategy To Access a Library of Peptidouridine-Containing Small Molecules
Name
nihms-1811277.pdf
Description
Accepted version
Size
1.05 MB
Format
Adobe PDF
Checksum (MD5)
98ddd69dd8e789670732daf977e6bfe9
Author(s)
Arbour, Christine A
Imperiali, Barbara
Date Issued
2022
Journal
Organic Letters
Publisher
American Chemical Society (ACS)
Citation
Arbour, Christine A and Imperiali, Barbara. 2022. "Backbone-Anchoring, Solid-Phase Synthesis Strategy To Access a Library of Peptidouridine-Containing Small Molecules." Organic Letters, 24 (11).
Version
Author's final manuscript
Abstract
Nucleoside diphosphate sugar (NDP-sugar) substrates provide the inspiration for nucleoside analogue inhibitor scaffolds. By employing solid-phase synthesis, we provide a method to access a library of peptidouridine inhibitors with both minimal compound handling and purification steps. Specifically, this strategy is exemplified by generating uridine diphosphate sugar (UDP-sugar) mimics, which allow for compound elaboration by altering the dipeptide composition, the N-terminal linkage, and a pendant aryl group. To exemplify the versatility, 41 unique nucleoside analogues are presented.
MIT Department
Massachusetts Institute of Technology. Department of Biology
Terms of Use
Creative Commons Attribution-Noncommercial-Share Alike
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DOI of Published Version
https://doi.org/10.1021/ACS.ORGLETT.2C00462
