Nucleoside derivative or salt thereof, polynucleotide synthesis reagent, method for producing polynucleotide, polynucleotide, and method for producing binding nucleic acid molecule
The present invention provides a novel nucleoside derivative or a salt thereof, a polynucleotide synthesis reagent, a method for producing a polynucleotide, a polynucleotide, and a method for producing a binding nucleic acid molecule. The nucleoside derivative or a salt thereof of the present invention is represented by the following chemical formula (1): where in the chemical formula (1), Su is an atomic group having a sugar skeleton at a nucleoside residue or an atomic group having a sugar phosphate skeleton at a nucleotide residue, and may or may not have a protecting group, L 1 and L 2 are each independently a straight-chain or branched, saturated or unsaturated hydrocarbon group having 2 to 10 carbon atoms, X 1 and X 2 are each independently an imino group (—NR 1 —), an ether group (—O—), or a thioether group (—S—), and the R 1 is a hydrogen atom or a straight-chain or branched, saturated or unsaturated hydrocarbon group having 2 to 10 carbon atoms.
1. A nucleoside derivative or a salt thereof, represented by the following chemical formula (1):
wherein, in the chemical formula (1),
Su is an atomic group having a sugar skeleton at a nucleoside residue or an atomic group having a sugar phosphate skeleton at a nucleotide residue, and may or may not have a protecting group,
L 1 and L 2 are each independently a straight-chain or branched, saturated or unsaturated hydrocarbon group having 2 to 10 carbon atoms,
X 1 and X 2 are each independently an imino group (—NR 1 —), an ether group (—O—), or a thioether group (—S—), and
the R 1 is a hydrogen atom or a straight-chain or branched, saturated or unsaturated hydrocarbon group having 2 to 10 carbon atoms.
2. The nucleoside derivative or a salt thereof according to claim 1 , wherein the X 1 is an imino group (—NR 1 —).
3. The nucleoside derivative or a salt thereof according to claim 1 , wherein the X 2 is an imino group (—NR 1 —).
4. The nucleoside derivative or a salt thereof according to claim 2 , wherein the R 1 is a hydrogen atom.
5. The nucleoside derivative or a salt thereof according to claim 1 , wherein the L 1 is a vinylene group (—CH═CH—).
6. The nucleoside derivative or a salt thereof according to claim 1 , wherein the L 2 is an ethylene group (—CH 2 —CH 2 —).
7. The nucleoside derivative or a salt thereof according to claim 1 , wherein the atomic group having a sugar skeleton at a nucleoside residue or the atomic group having a sugar phosphate skeleton at a nucleotide residue is represented by the following chemical formula (2):
wherein, in the chemical formula (2),
R 2 is a hydrogen atom, a protecting group, or a group represented by the following chemical formula (3),
R 3 is a hydrogen atom, a protecting group, or a phosphoramidite group, and
R 4 is a hydrogen atom, a fluorine atom, a hydroxyl group, an amino group, or a mercapto group,
wherein, in the chemical formula (3),
Y is an oxygen atom or a sulfur atom,
Z is a hydroxyl group or an imidazole group, and
m is an integer of 1 to 10.
8. The nucleoside derivative or a salt thereof according to claim 1 , wherein the nucleoside derivative represented by the chemical formula (1) is a nucleoside derivative represented by the following chemical formula (4):
9. A polynucleotide synthesis reagent comprising a nucleotide derivative or a salt thereof represented by the following chemical formula (1):
wherein, in the chemical formula (1),
Su is an atomic group having a sugar phosphate skeleton at a nucleotide residue, and may or may not have a protecting group,
L 1 and L 2 are each independently a straight-chain or branched, saturated or unsaturated hydrocarbon group having 2 to 10 carbon atoms,
X 1 and X 2 are each independently an imino group (—NR 1 —), an ether group (—O—), or a thioether group (—S—), and
the R 1 is a hydrogen atom or a straight-chain or branched, saturated or unsaturated hydrocarbon group having 2 to 10 carbon atoms,
wherein the atomic group having a sugar phosphate skeleton at a nucleotide residue is represented by the following chemical formula (2):
wherein, in the chemical formula (2),
R 2 is a hydrogen atom, a protecting group, or a group represented by the following chemical formula (3),
R 3 is a hydrogen atom, a protecting group, or a phosphoramidite group, and
R 4 is a hydrogen atom, a fluorine atom, a hydroxyl group, an amino group, or a mercapto group,
wherein, in the chemical formula (3),
Y is an oxygen atom or a sulfur atom,
Z is a hydroxyl group or an imidazole group, and
m is an integer of 1 to 10.
10. A method for producing a polynucleotide, comprising the step of synthesizing a polynucleotide using a nucleotide derivative or a salt thereof represented by the following chemical formula (1):
wherein, in the chemical formula (1),
Su is an atomic group having a sugar phosphate skeleton at a nucleotide residue, and may or may not have a protecting group,
L 1 and L 2 are each independently a straight-chain or branched, saturated or unsaturated hydrocarbon group having 2 to 10 carbon atoms,
X 1 and X 2 are each independently an imino group (—NR 1 —), an ether group (—O—), or a thioether group (—S—), and
the R 1 is a hydrogen atom or a straight-chain or branched, saturated or unsaturated hydrocarbon group having 2 to 10 carbon atoms,
wherein the atomic group having a sugar phosphate skeleton at a nucleotide residue is represented by the following chemical formula (2):
wherein, in the chemical formula (2),
R 2 is a hydrogen atom, a protecting group, or a group represented by the following chemical formula (3),
R 3 is a hydrogen atom, a protecting group, or a phosphoramidite group, and
R 4 is a hydrogen atom, a fluorine atom, a hydroxyl group, an amino group, or a mercapto group,
wherein, in the chemical formula (3),
Y is an oxygen atom or a sulfur atom,
Z is a hydroxyl group or an imidazole group, and
m is an integer of 1 to 10.