Dideoxynucleoside derivatives
View Patent ↗The invention provides a 5′-amino-2′-fluoro-2′,5′-dideoxynucleoside compound represented by the formula [1]: wherein R 1 represents a nucleic acid base which may have a protecting group; R 2 represents a hydrogen atom or an amino protecting group; and R 3 represents a hydrogen atom or a hydroxyl protecting group. The invention also provides a dideoxynucleoside-insoluble carrier bound substance and an oligonucleotide analogue involving the dideoxynucleoside compound.
1. A 5′-amino-2′-fluoro-2′,5′-dideoxynucleoside compound represented by the following formula [1]:
wherein R 1 represents a nucleic acid base which may have a protecting group; R 2 represents a hydrogen atom or an amino protecting group; and R 3 represents a hydrogen atom or a hydroxyl protecting group.
2. The compound of claim 1 , wherein the 5′-amino-2′-fluoro-2′,5′-dideoxynucleoside compound represented by the formula [1] is a compound represented by the following formula [3]:
wherein R 1 represents a nucleic acid base which may have a protecting group; and R 2 represents a hydrogen atom or an amino protecting group.
3. The compound of claim 1 , wherein the 5′-amino-2′-fluoro-2′,5′-dideoxynucleoside compound represented by the formula [1] is a compound represented by the following formula [5]:
wherein R 1 represents a nucleic acid base which may have a protecting group; R 2 represents a hydrogen atom or an amino protecting group; and i-Pr represents an isopropyl group.
4. A dideoxynucleoside-insoluble carrier bound substance that is a 5′-amino-2′-fluoro-2′,5′-dideoxynucleoside compound represented by the following formula [6]:
wherein R 1 represents a nucleic acid base which may have a protecting group; R 2 represents a hydrogen atom or an amino protecting group; and R 4 represents a solid support with a linker moiety.
5. An oligonucleotide analogue comprising a 5′-amino-2′-fluoro-2′,5′-dideoxynucleoside monomeric unit represented by the following formula [1]:
wherein R 1 represents a nucleic acid base which may have a protecting group; R 2 represents a hydrogen atom or an amino protecting group; and R 3 represents a hydrogen atom or a hydroxyl protecting group, wherein an oligonucleoside chain or oligonucleotide chains are attached via chemical linkage in place of one or both of substituent groups R 2 and R 3 of formula [1].
6. The oligonucleotide analogue of claim 5 , wherein the chemical linkage is a phosphate diester linkage or a phosphormonoamidate-monoester linkage.