Prodan-containing nucleotide and use thereof

A nucleoside or nucleotide derivative represented by formula (9):

• wherein R5 is a substituent represented by formula (10):
• wherein R7 is —H or —OH;
• n is 0, 1, 2, or 3;
• and R6 is ═O or —NH2, with the proviso that when R6 is ═O, H is attached to the 1-position N of the pyrimidine ring, and the bond between the 1-position N and the 6-position C is a single bond;
• or a substituent represented by formula (11):
• wherein R7 is —H or —OH;
• n is 0, 1, 2, or 3;
• and R8 is —OH, ═O, or —NH2, with the proviso that when R8 is —OH or —NH2, R9 is H;
• when R8 is ═O, R9 is —NH2;
• and when R8 is ═O, H is attached to the 1-position N of the purine ring, and the bond between the 1-position N and the 6-position C is a single bond.

A polynucleotide derivative wherein one or more nucleotides are substituted by a nucleotide derivative represented by formula (17):

• wherein R10 is a substituent represented by formula (18):
• wherein R12 is —H or —OH;
• and R11 is ═O or —NH2, with the proviso that when R11 is ═O, H is attached to the 1-position N of the pyrimidine ring, and the bond between the 1-position N and the 6-position C is a single bond;
• or a substituent represented by formula (19):
• wherein R12 is —H or —OH;
• and R13 is —OH, ═O, or —NH2, with the proviso that when R13 is —OH or —NH2, R14 is H;
• when R13 is ═O, R14 is —NH2;
• and when R13 is ═O, H is attached to the 1-position N of the purine ring, and the bond between the 1-position N and the 6-position C is a single bond.

A compound represented by formula (25):

• wherein R15 is a substituent represented by formula (26):
• wherein R17 is —H or —OH;
• DMTrO— is a dimethoxytrityl group;
• and R16 is ═O or —NH2, with the proviso that when R16 is ═O, H is attached to the 1-position N of the pyrimidine ring, and the bond between the 1-position N and the 6-position C is a single bond;
• or a substituent represented by formula (27):
• wherein R17 is —H or —OH;
• DMTrO— is a dimethoxytrityl group;
• and R18 is —OH, ═O, or —NH2, with the proviso that when R18 is —OH or —NH2, R19 is H;
• when R18 is ═O, R19 is —NH2;
• and when R18 is ═O, H is attached to the 1-position N of the purine ring, and the bond between the 1-position N and the 6-position C is a single bond.

A compound represented by formula (33):

• wherein R20 is a substituent represented by formula (34):
• wherein R22 is —H or —OH;
• DMTrO— is a dimethoxytrityl group;
• and R21 is ═O or —NH2, with the proviso that when R21 is ═O, H is attached to the 1-position N of the pyrimidine ring, and the bond between the 1-position N and the 6-position C is a single bond;
• or a substituent represented by formula (35):
• wherein R22 is —H or —OH;
• DMTrO— is a dimethoxytrityl group;
• and R23 is —OH, ═O, or —NH2, with the proviso that when R23 is —OH or —NH2, R24 is H;
• when R23 is ═O, R24 is —NH2;
• and when R23 is ═O, H is attached to the 1-position N of the purine ring, and the bond between the 1-position N and the 6-position C is a single bond.