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US 7,741,472 B2Granted
Polynucleotide containing a phosphate mimetic
AssigneeRoche Diagnostics Operations, Inc.
InventorsDieter Heindl, Dirk Kessler
Life of this patent
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Abstract
The present invention concerns modified oligonucleotides and processes for their production wherein these oligonucleotides contain at least once the structure P═N-Acc where Acc is an electron acceptor or an electron acceptor substituted with a residue R and R is any organic substituent.
Claims7
A chemical compound comprising at least once the structure
- wherein
- A represents the 5′ end of a nucleotide, a nucleotide chain, or a linker bound to a solid phase,
- B represents the 3′ end of a nucleotide, a nucleotide chain, or a linker,
- D is OH or CH3, and
- Acc is an electron acceptor or an electron acceptor substituted with a residue R wherein R is an organic substituent, wherein Acc is selected from the group consisting of
- CN,
- SO2—R′, in which R′ comprises at least one amino-substituted alkyl, an optionally substituted aryl or an optionally substituted heterocycle, and
- a six membered N+ heterocycle with at least one alkylated N-atom in ortho- or para-position, said heterocycle selected from the group consisting of pyridinium, pyrimidinium, and chinolinium.
5 more elements
A process for producing a modified oligonucleotide comprising the steps of
- providing a trivalent phosphorus derivative having a structure
- wherein E represents a methyl group or a protected hydroxyl group, A represents a 5′ end of a nucleotide, a nucleotide chain, or a linker bound to a solid phase, and B represents a 3′ end of a nucleotide, or a nucleotide chain, or a linker,
- reacting the trivalent phosphorus derivative with an azide having the structure
- N═N═N-Acc
- wherein Acc is an electron acceptor or an electron acceptor substituted with a residue R wherein R is an organic substituent and Acc is selected from the group consisting of CN, SO2—R′, in which R′ contains at least one amino-substituted alkyl, an optionally substituted aryl or an optionally substituted heterocycle, and a six membered N+ heterocycle with at least one alkylated N-atom in ortho- or para-position, said heterocycle being selected from the group consisting of pyridinium, pyrimidinium and chinolinium,
- under conditions whereby said modified oligonucleotide is formed.
3 more elements
A process for producing a modified oligonucleotide comprising the steps of
- reacting a 3′ phosphoramidite with the 5′ OH end of a nascent oligonucleotide chain to produce a trivalent phosphorus derivative and
- then reacting the trivalent phosphorus derivative with an azide having the structure
- N═N═N-Acc
- in which Acc is an electron acceptor or an electron acceptor substituted with a residue R and R is any organic substituent, and Acc is selected from a group consisting of CN, SO2—R′, in which R′ contains at least one amino-substituted alkyl, an optionally substituted aryl or an optionally substituted heterocycle, and a six membered N+ heterocycle with at least one alkylated N-atom in ortho- or para-position, said heterocycle being selected from a group consisting of pyridinium, pyrimidinium and chinolinium, under conditions whereby said modified oligonucleotide is formed.
1 more element
Dependencies are inferred from the claim text.