Nucleic acid conjugate

A compound represented by the following formula 8:

• wherein
• R1 and R2 are each independently a hydrogen atom, a t-butoxycarbonyl group, a benzyloxycarbonyl group, a 9-fluorenylmethyloxycarbonyl group, —CO—R4, or —CO—B4-[(P9-Q8)q7-T3-L3]p3,
• P9 and T3 are each independently absent, or —CO—, —NH—, —O—, —S—, —O—CO—, —S—CO—, —NH—CO—, —CO—O—, —CO—S— or —CO—NH—,
• Q8 is absent, or substituted or unsubstituted alkylene having 1 to 12 carbon atoms or —(CH2CH2O)n1—CH2CH2— wherein n1 is an integer of 0 to 99,
• B4 is a bond, or any structure represented by the following formula 8-1, wherein each of the terminal dots in each structure is a binding site to a carbonyl group or P9, and m7, m8, m9 and m10 are each independently an integer of 0 to 10:
• p3 is an integer of 1, 2 or 3,
• q7 is an integer of 0 to 10,
• L3 is a sugar ligand,
• Y is —O—(CH2)m11—NH— or —NH—CO—(CH2)m12—NH— wherein m11 and m12 are each independently an integer of 1 to 10,
• R3 is a hydrogen atom, a t-butoxycarbonyl group, a benzyloxycarbonyl group, a 9-fluorenylmethyloxycarbonyl group, —CO—R4, —CO—(CH2CH2O)n2—CH2CH2—N3, or —CO-Q9-B5-(Q10-P10)q8—X1 wherein n2 is an integer of 0 to 99,
• P10 is absent, or —CO—, —NH—, —O—, —S—, —O—CO—, —S—CO—, —NH—CO—, —CO—O—, —CO—S— or —CO—NH—,
• Q9 and Q10 are each independently absent, or substituted or unsubstituted alkylene having 1 to 12 carbon atoms or —(CH2CH2O)n3—CH2CH2— wherein n3 is an integer of 0 to 99,
• B5 is any structure represented by the following formula 8-2, wherein the broken lines respectively mean bonds to Q9 and Q10:
• q8 is an integer of 0 to 10,
• X1 is a hydrogen atom or a solid-phase support, and
• R4 is an alkyl group having 2 to 10 carbon atoms substituted with 1 or 2 substituents selected from the group consisting of an amino group unsubstituted for substituted with the t-butoxycarbonyl group, a benzyloxycarbonyl group or a 9-fluorenylmethyloxycarbonyl group, a carboxy group, a maleimide group, and an aralkyloxycarbonyl group.

A compound represented by the following formula 9:

• wherein
• R5 and R6 are each independently a hydrogen atom, a t-butoxycarbonyl group, a benzyloxycarbonyl group, a 9-fluorenylmethyloxycarbonyl group, —CO—R4′, or —CO-Q11-(P11-Q11′)q9-T4-L4,
• P11 and T4 are each independently absent, or —CO—, —NH—, —O—, —S—, —O—CO—, —S—CO—, —NH—CO—, —CO—O—, —CO—S— or —CO—NH—,
• each of Q11 and Q11′ is absent, or substituted or unsubstituted alkylene having 1 to 12 carbon atoms or —(CH2CH2O)n4—CH2CH2— wherein n4 is an integer of 0 to 99,
• q9 is an integer of 0 to 10,
• L4 is a sugar ligand,
• Y′ is —O—(CH2)m11′—NH— or —NH—CO—(CH2)m12′—NH— wherein m11′ and m12′ are each independently an integer of 1 to 10,
• R3′ is a hydrogen atom, a t-butoxycarbonyl group, a benzyloxycarbonyl group, a 9-fluorenylmethyloxycarbonyl group, —CO—R4′, —CO—(CH2CH2O)n2′—CH2CH2—N3, or —CO-Q9′-B5′-(Q10′-P10′)q8′—X1′ wherein n2′ is an integer of 0 to 99,
• P10′ is absent, or —CO—, —NH—, —O—, —S—, —O—CO—, —S—CO—, —NH—CO—, —CO—O—, —CO—S— or —CO—NH—,
• Q9′ and Q10′ are each independently absent, or substituted or unsubstituted alkylene having 1 to 12 carbon atoms or —(CH2CH2O)n3′—CH2CH2— wherein n3′ is an integer of 0 to 99,
• B5′ is any structure represented by the following formula 9-1, wherein the broken lines respectively mean bonds to Q9′ and Q10′:
• Formula 9-1:
• q8′ is an integer of 0 to 10,
• X1′ is a hydrogen atom or a solid-phase support, and
• R4′ is an alkyl group having 2 to 10 carbon atoms substituted with 1 or 2 substituents selected from the group consisting of an amino group unsubstituted or substituted with a t-butoxycarbonyl group, a benzyloxycarbonyl group or a 9-fluorenylmethyloxycarbonyl group, a carboxy group, a maleimide group, and an aralkyloxycarbonyl group.

A compound represented by the following formula 10:

• wherein
• R7 and R8 are each independently a hydroxy group, a t-butoxy group, a benzyloxy group, —NH—R10, or —NH-Q12-(P12-Q12′)q10-T5-L5,
• P12 and T5 are each independently absent, or —CO—, —NH—, —O—, —S—, —O—CO—, —S—CO—, —NH—CO—, —CO—O—, —CO—S— or —CO—NH—,
• each of Q12 and Q12′ is absent, or substituted or unsubstituted alkylene having 1 to 12 carbon atoms or —(CH2CH2O)n5—CH2CH2— wherein n5 is an integer of 0 to 99,
• L5 is a sugar ligand,
• Y2 is —O—(CH2)m13—NH— or —NH—CO—(CH2)m14—NH— wherein m13 and m14 are each independently an integer of 1 to 10,
• q10 is an integer of 0 to 10,
• R9 is a hydrogen atom, a t-butoxycarbonyl group, a benzyloxycarbonyl group, a 9-fluorenylmethyloxycarbonyl group, —CO—R10, —CO—(CH2CH2O)n6—CH2CH2—N3, or —CO-Q13-B6-(Q14-P13)q11—X2 wherein n6 is an integer of 0 to 99,
• P13 is absent, or —CO—, —NH—, —O—, —S—, —O—CO—, —S—CO—, —NH—CO—, —CO—O—, —CO—S— or —CO—NH—,
• Q13 and Q14 are each independently absent, or substituted or unsubstituted alkylene having 1 to 12 carbon atoms or —(CH2CH2O)n7—CH2CH2— wherein n7 is an integer of 0 to 99,
• B6 is any structure represented by the following formula 10-1, wherein the broken lines respectively mean bonds to Q13 and Q14:
• q11 is an integer of 0 to 10,
• X2 is a hydrogen atom or a solid-phase support, and
• R10 is an alkyl group having 2 to 10 carbon atoms substituted with 1 or 2 substituents selected from the group consisting of an amino group unsubstituted or substituted with a t-butoxycarbonyl group, a benzyloxycarbonyl group or a 9-fluorenylmethyloxycarbonyl group, a carboxy group, a maleimide group, and an aralkyloxycarbonyl group.