Abstract
A convergent synthesis provided nearly perfect τ-ADP-ribosylated histidine isosteres (His*-τ-ADPr) via a copper(I)-catalyzed cycloaddition between an azido-ADP-ribosyl analogue and an oligopeptide carrying a propargyl glycine. Both α- and β-configured azido-ADP-ribosyl analogues have been synthesized. The former required participation of the C-2 ester functionality during glycosylation, while the latter was obtained in high stereoselectivity from an imidate donor with a nonparticipating para-methoxy benzyl ether. Four His*-τ-ADPr peptides were screened against a library of human ADP-ribosyl hydrolases.
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CITATION STYLE
Minnee, H., Rack, J. G. M., Van Der Marel, G. A., Overkleeft, H. S., Codée, J. D. C., Ahel, I., & Filippov, D. V. (2022). Mimetics of ADP-Ribosylated Histidine through Copper(I)-Catalyzed Click Chemistry. Organic Letters, 24(21), 3776–3780. https://doi.org/10.1021/acs.orglett.2c01300
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