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Method for the synthesis of phosphorus atom modified nucleic acids

  • US 9,394,333 B2
  • Filed: 12/02/2009
  • Issued: 07/19/2016
  • Est. Priority Date: 12/02/2008
  • Status: Active Grant
First Claim
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1. A method for a synthesis of a nucleic acid comprising a chiral X-phosphonate moiety comprising:

  • reacting a molecule comprising an achiral H-phosphonate moiety, a chiral reagent, and a nucleoside comprising a 5′

    -OH moiety to form a condensed intermediate; and

    converting the condensed intermediate to the nucleic acid comprising a chiral X-phosphonate moiety;

    wherein;

    each instance of X is independently an optionally substituted group selected from alkyl, alkoxy, aryl, alkylthio, acyl, —

    NRfRf, alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, —

    S

    Z+, Se

    Z+, and —

    BH3

    Z+;

    each instance of Rf is independently hydrogen, alkyl, alkenyl, alkynyl, or aryl; and

    Z+ is ammonium ion, alkylammonium ion, heteroaromatic iminium ion, or heterocyclic iminium ion, any of which is primary, secondary, tertiary or quaternary, or Z+ is a monovalent metal ion.

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