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Monomers for preparation of amide linked RNA: Synthesis of C3'-homologated nucleoside amino acids from d-xylose.

ABSTRACT: Amides as neutral and hydrophobic internucleoside linkages in RNA are highly interesting modifications for RNA interference. However, testing amides in siRNAs is hampered by the shortage of efficient methods to synthesize the monomeric building blocks, the nucleoside amino acid equivalents. This paper reports an efficient synthesis of protected ribonucleoside 5'-amino 3'-carboxylic acids from d-xylose in 14 steps 7% overall yield. The key features that ensure efficiency and ease of operations are chemoselective reduction of the ester and minimization of protecting group manipulation.

SUBMITTER: Tanui P

PROVIDER: S-EPMC2921610 | biostudies-literature | 2010 Jul

REPOSITORIES: biostudies-literature

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Monomers for preparation of amide linked RNA: Synthesis of C3'-homologated nucleoside amino acids from d-xylose.

Tanui Paul P Kullberg Martin M Song Ni N Chivate Yashodhan Y Rozners Eriks E

Tetrahedron 20100701 27-28

Amides as neutral and hydrophobic internucleoside linkages in RNA are highly interesting modifications for RNA interference. However, testing amides in siRNAs is hampered by the shortage of efficient methods to synthesize the monomeric building blocks, the nucleoside amino acid equivalents. This paper reports an efficient synthesis of protected ribonucleoside 5'-amino 3'-carboxylic acids from d-xylose in 14 steps 7% overall yield. The key features that ensure efficiency and ease of operations ar ...[more]

PMID: 20725640

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