Nucleoside Phosphorylases make N7-xanthosine

Author:

Westarp SarahORCID,Brandt FelixORCID,Neumair LenaORCID,Betz ChristinaORCID,Dagane Amin,Kemper SebastianORCID,Jacob Christoph R.ORCID,Neubauer PeterORCID,Kurreck AnkeORCID,Kaspar FelixORCID

Abstract

AbstractModern, highly evolved nucleoside-processing enzymes are known to exhibit perfect regioselectivity over the glycosylation of purine nucleobases at N9. We herein report an exception to this paradigm. Wild-type nucleoside phosphorylases also furnish N7-xanthosine, a “non-native” ribosylation regioisomer of xanthosine. This unusual nucleoside possesses several atypical physicochemical properties such as redshifted absorption spectra, a high equilibrium constant of phosphorolysis and low acidity. Ultimately, the biosynthesis of this previously unknown natural product illustrates how even highly evolved, essential enzymes from primary metabolism are imperfect catalysts.

Funder

Deutsche Forschungsgemeinschaft

Publisher

Springer Science and Business Media LLC

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