Title: Design and synthesis of α-carboxy nucleoside phosphonate analogues and evaluation as HIV-1 reverse transcriptase-targeting agents
Authors: Keane, Sarah J
Ford, Alan
Mullins, Nicholas D
Maguire, Nuala M
Legigan, Thibaut
Balzarini, Jan
Maguire, Anita R # ×
Issue Date: Mar-2015
Publisher: American Chemical Society
Series Title: Journal of Organic Chemistry vol:80 pages:2479-2493
Abstract: The synthesis of the first series of a new class of nucleoside phosphonate analogues is described. Addition of a carboxyl group at the α position of carbocyclic nucleoside phosphonate analogues leads to a novel class of potent HIV reverse transcriptase (RT) inhibitors, α-carboxy nucleoside phosphonates (α-CNPs). Key steps in the synthesis of the compounds are Rh-catalyzed O-H insertion and Pd-catalyzed allylation reactions. In cell-free assays, the final products are markedly inhibitory against HIV RT and do not require phosphorylation to exhibit anti-RT activity, which indicates that the α-carboxyphosphonate function is efficiently recognized by HIV RT as a triphosphate entity, an unprecedented property of nucleoside monophosph(on)ates.
ISSN: 0022-3263
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Laboratory of Virology and Chemotherapy (Rega Institute)
× corresponding author
# (joint) last author

Files in This Item:
File Description Status SizeFormat
2015029.pdf Published 694KbAdobe PDFView/Open Request a copy
Keane J Org Chem 2015.pdf Published 461KbAdobe PDFView/Open Request a copy

These files are only available to some KU Leuven Association staff members


All items in Lirias are protected by copyright, with all rights reserved.

© Web of science