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Updated: Jun 14, 2026
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Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
Published on: April 15, 2013
1-(beta-D-Erythrofuranosyl)adenosine
Paul C Kline1, Hongqiu Zhao, Bruce C Noll
1Department of Chemistry, Middle Tennessee State University, Murfreesboro, TN 37132, USA.
Summary
Beta-erythroadenosine, a beta-adenosine derivative, exhibits distinct molecular conformations in its crystal structure. Its binding to 5'-fluorodeoxyadenosine synthase reveals specific furanose and base orientations crucial for enzyme interaction.
Area of Science:
- Biochemistry
- Crystallography
- Molecular Biology
Background:
- Beta-erythroadenosine (I) is a derivative of beta-adenosine (II), lacking the C5' hydroxymethyl substituent.
- Understanding the conformational flexibility of nucleoside analogs is vital for drug design and enzyme inhibition studies.
Purpose of the Study:
- To elucidate the crystal structure and conformational properties of beta-erythroadenosine.
- To investigate the binding mode of beta-erythroadenosine to 5 extprime-fluorodeoxyadenosine synthase.
Main Methods:
- Single crystal X-ray diffraction analysis of beta-erythroadenosine.
- Cocrystallization and structural determination of beta-erythroadenosine bound to 5 extprime-fluorodeoxyadenosine synthase.
Main Results:
- Beta-erythroadenosine crystallizes with two independent molecules (IA and IB) exhibiting different furanose and N-glycoside conformations.
- The crystal structure of the cocrystal shows beta-erythroadenosine in a near-ideal (O)E furanose conformation with an anti base orientation.
- Pseudorotational parameters (P and tau(m)) were determined for both independent molecules and the enzyme-bound form.
Conclusions:
- The study reveals significant conformational polymorphism in beta-erythroadenosine.
- The enzyme-bound conformation provides insights into the molecular interactions governing substrate binding to 5 extprime-fluorodeoxyadenosine synthase.
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