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Nucleoside Phosphorylases make N7-xanthosine.

Sarah Westarp1,2, Felix Brandt3, Lena Neumair1

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|April 29, 2024
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Enzymes typically attach nucleosides to purine bases at a specific site (N9). However, nucleoside phosphorylases also create a different form, N7-xanthosine, revealing these enzymes are not perfect catalysts.

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Area of Science:

  • Biochemistry
  • Enzymology
  • Natural Product Biosynthesis

Background:

  • Nucleoside-processing enzymes are highly evolved with established regioselectivity.
  • Glycosylation of purine nucleobases predominantly occurs at the N9 position.

Purpose of the Study:

  • To investigate exceptions to the N9 regioselectivity in nucleoside glycosylation.
  • To characterize a novel ribosylation regioisomer of xanthosine.

Main Methods:

  • Enzymatic assays using wild-type nucleoside phosphorylases.
  • Spectroscopic analysis of the synthesized nucleoside.
  • Determination of physicochemical properties, including absorption spectra and phosphorolysis equilibrium.

Main Results:

  • Wild-type nucleoside phosphorylases were found to produce N7-xanthosine, a regioisomer of xanthosine.
  • N7-xanthosine exhibits atypical properties: redshifted absorption spectra, high phosphorolysis equilibrium constant, and low acidity.
  • This represents a deviation from the expected N9 glycosylation.

Conclusions:

  • The biosynthesis of N7-xanthosine demonstrates that even highly evolved enzymes from primary metabolism can be imperfect catalysts.
  • This finding challenges the paradigm of perfect regioselectivity in nucleoside processing.
  • A previously unknown natural product, N7-xanthosine, has been identified and characterized.