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US 2003/0125291 A1Published application
Xylofuranosly-containing nucleoside phosphoramidites and polynucleotides
AssigneeRibozyme Pharmaceuticals, Inc.
InventorsJasenka Matulic-Adamic, Leonid Beigelman
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Abstract
Novel xylo nucleoside or xylo nucleotide analogs, polynucleotides comprising xylo nucleotide substitution, processes for their synthesis and incorporation into polynucleotides.
Claims29
A compound having the formula I:
- 5
- wherein,
- R1 is OH, O—R3, wherein R3 is independently a moiety selected from a group consisting of alkyl, alkenyl, alkynyl, aryl, alkylaryl, carbocyclic aryl, heterocyclic aryl, amide and ester, C—R3, wherein R3 is independently a moiety selected from a group consisting of alkyl, alkenyl, alkynyl, aryl, alkylaryl, carbocyclic aryl, heterocyclic aryl, amide and ester, halo, NHR4 wherein R4 is independently a moiety selected from a group consisting of alkyl (C1-22), acyl (C1-22), substituted or unsubstituted aryl), or OCH2SCH3 (methylthiomethyl), ONHR5 where R5 is independently a moiety selected from a group consisting of H, aminoacyl group, peptidyl group, biotinyl group, cholesteryl group, lipoic acid residue, retinoic acid residue, folic acid residue, ascorbic acid residue, nicotinic acid residue, 6-aminopenicillanic acid residue, 7-aminocephalosporanic acid residue, alkyl, alkenyl, alkynyl, aryl, alkylaryl, carbocyclic aryl, heterocyclic aryl, amide or ester, ON=R6, where R6 is independently pyridoxal residue, pyridoxal-5-phosphate residue, 13-cis-retinal residue, 9-cis-retinal residue, alkyl, alkenyl , alkynyl, alkylaryl, carbocyclic alkylaryl, or heterocyclic alkylaryl;
- B is independently a nucleotide base or its analog or hydrogen;
- X is independently a phosphorus-containing group;
- and
- R2 is independently blocking group or a phosphorus-containing group.
4 more elements
A process for the synthesis of a xylo ribonucleoside phosphoramidite comprising the steps of:
- a) oxidation of a 2′ and 5′-protected ribonucleoside using an oxidant followed by reduction using a reducing agent under conditions suitable for the formation of 2′ and 5′-protected xylofuranosyl nucleoside;
- and
- b) phosphitylation under conditions suitable for the formation of xylofuranosyl nucleoside phosphoramidite.;
Dependencies are inferred from the claim text.