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Nucleoside Triphosphates - From Synthesis to Biochemical Characterization
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Resolved P-metalated nucleoside phosphoramidites.

Erica J Miller1, Kevin J Garcia, Erin C Holahan

  • 1Department of Chemistry, Bucknell University , Lewisburg, Pennsylvania 17837, United States.

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Researchers synthesized rare P-metalated nucleoside phosphoramidites. Gold was used as a metal center and then removed, allowing platinum to form a unique platinated dinucleoside with high stereoselectivity.

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Area of Science:

  • Organometallic Chemistry
  • Nucleoside Chemistry
  • Synthetic Chemistry

Background:

  • P-metalated nucleoside phosphoramidites are rare and synthetically challenging compounds.
  • Previous methods for metalation often involve stable metal complexes that are difficult to remove.

Purpose of the Study:

  • To describe the synthesis of resolved P-metalated nucleoside phosphoramidites.
  • To develop a method for the facile removal of the metal center.
  • To explore the subsequent metalation with platinum.

Main Methods:

  • Synthesis of gold-metalated nucleoside phosphoramidites.
  • Demelation using basic phosphines or solid-supported triphenylphosphine.
  • Platination of the free nucleoside phosphoramidite.

Main Results:

  • Successfully synthesized resolved P-metalated nucleoside phosphoramidites.
  • Demonstrated efficient removal of the gold center.
  • Generated a unique platinated dinucleoside species with a diastereomeric ratio exceeding 99:1.

Conclusions:

  • The developed method allows for the synthesis and manipulation of P-metalated nucleoside phosphoramidites.
  • This provides access to novel platinum-containing dinucleoside species with high stereochemical control.