Method for the synthesis of phosphorus atom modified nucleic acids
First Claim
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1. A method for the 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;
the nucleic acid comprises a modified sugar, wherein the modified sugar contains one or more substituents at the 2′
-position selected from the group consisting of F, CF3, CN, N3, NO, NO2, O-, S-, or N-alkyl;
O-, S-, or N-alkenyl;
O-, S-, or N-alkynyl;
or O-alkyl-O-alkyl, O-alkyl-N-alkyl or N-alkyl-O-alkyl wherein the alkyl, alkenyl and alkynyl may be substituted or unsubstituted C1-C10 alkyl or C2-C10 alkenyl and alkynyl;
each instance of X is independently alkyl, alkoxy, aryl, alkylthio, acyl, —
NRfRf, alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, —
S−
Z+, —
Se−
Z+, or —
BH3−
Z+;
each instance of Rf is independently hydrogen, alkyl, alkenyl, alkynyl, or aryl;
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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Abstract
Described herein are methods of syntheses of phosphorous atom-modified nucleic acids comprising chiral X-phosphonate moieties. The methods described herein provide backbone-modified nucleic acids in high diasteteomeric purity via an asymmetric reaction of an achiral molecule comprising a chemically stable H-phophonate moiety with a nucleoside/nucleotide.
751 Citations
17 Claims
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1. A method for the synthesis of a nucleic acid comprising a chiral X-phosphonate moiety comprising:
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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; andconverting the condensed intermediate to the nucleic acid comprising a chiral X-phosphonate moiety, wherein; the nucleic acid comprises a modified sugar, wherein the modified sugar contains one or more substituents at the 2′
-position selected from the group consisting of F, CF3, CN, N3, NO, NO2, O-, S-, or N-alkyl;
O-, S-, or N-alkenyl;
O-, S-, or N-alkynyl;
or O-alkyl-O-alkyl, O-alkyl-N-alkyl or N-alkyl-O-alkyl wherein the alkyl, alkenyl and alkynyl may be substituted or unsubstituted C1-C10 alkyl or C2-C10 alkenyl and alkynyl;each instance of X is independently alkyl, alkoxy, aryl, alkylthio, acyl, —
NRfRf, alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, —
S−
Z+, —
Se−
Z+, or —
BH3−
Z+;each instance of Rf is independently hydrogen, alkyl, alkenyl, alkynyl, or aryl; 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. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17)
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Specification
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Current AssigneeWAVE Life Sciences Ltd.
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Original AssigneeWAVE Life Sciences Ltd.
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InventorsWada, Takeshi, Shimizu, Mamoru
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Primary Examiner(s)Riley, Jezia
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Application NumberUS15/608,123Publication NumberTime in Patent Office756 DaysField of Search536 231, 536 243, 536 253US Class CurrentCPC Class CodesC07H 1/00 Processes for the preparati...C07H 21/00 Compounds containing two or...
