Abstract: Problem To provide a chiral nucleic acid adjuvant and anti-allergic agent having anti-allergic effect. Solution An adjuvant which comprises oligonucleotides which comprise two to four CpG motifs each represented by 5?-X1CpGX2-3? and has a length of 14 to 32 nucleotides, wherein a nucleic acid at 3? end side of at least two CpG motifs is connected by phosphorothioate linkage, wherein each nucleic acids at 3? end and 5? end of the oligonucleotide is S type nucleic acids connected by phosphorothioate linkage, and wherein the oligonucleotide comprises at least one nucleic acid without phosphorothioate modification. The present invention relates to an adjuvant comprising the oligonucleotide represented by the sequence number 67. The present invention relates to an anti-allergic agent comprising these adjuvant.

Abstract: Summary Problem The purpose of the present invention is to provide: a chiral nucleic acid adjuvant having anti-tumor activity; and an anti-tumor agent. Solution The present invention relates to an adjuvant for anti-tumor agent, wherein the adjuvant comprises oligonucleotides which comprise two to four CpG motif each represented by 5?-X1CpGX2-3? and has a length of 14 to 32 nucleotides, wherein a nucleic acid at 3? end side of at least two CpG motifs is connected by phosphorothioate linkage, wherein each nucleic acid at 3? end and 5? end of the oligonucleotide is S type nucleic acid connected by phosphorothioate linkage, and wherein the oligonucleotide comprises at least one nucleic acid without phosphorothioate modification. The present invention relates to an anti-tumor agent containing its adjuvant.

Abstract: Problem The purpose of the present invention is to provide: a chiral nucleic acid adjuvant having immunity-inducing activity and an immunity-inducing activator. Solution The present invention relates to an adjuvant which comprises oligonucleotides which comprise two to four sequences each represented by 5?-X1CpG X2-3? and has a length of 14 to 32 nucleotides, wherein a nucleic acid at 3? end side of at least two CpG motifs is connected by phosphorothioate linkage, wherein each nucleic acids at 3? end and 5? end of the oligonucleotide is S type nucleic acids connected by phosphorothioate linkage, and wherein the oligonucleotide comprises at least one nucleic acid without phosphorothioate modification. The present invention relates to an immunity-inducible activator comprising the adjuvant.

Abstract: Described herein are methods of syntheses of phosphorous atom-modified nucleic acids comprising chiral X-phosphonate moieties. The methods described herein provide backbone-modified nucleic acids in high diasteteomeric purity via an asymmetric reaction of an achiral molecule comprising a chemically stable H-phosphonate moiety with a nucleoside/nucleotide.

Abstract: Problem The purpose of the present invention is to provide: a stereo isomer of a novel CpG oligonucleotide, which has excellent stability; and a CpG oligonucleotide which has a capability of producing interferon-? (IFN?). Solution The present invention relates to an oligonucleotide which contains two to four sequences each represented by the formula 5?-X1X2CpGX3X4-3? (formula (I)) and has a length of 14 to 32 nucleotides. In formula (I), CpG represents a non-methylated CpG residue having a phosphate skeleton modification, X1X2 represents any one of AA, AT, GA and GT, and X3X4 represents any one of TT, AT, AC and CG. The oligonucleotide has at least one phosphate skeleton modification at an S-form stereoisomer located at a site other than the CpG.

Abstract: To provide a chiral reagent or a salt thereof. The chiral reagent has following chemical formula (I). In the formula (I), G1 and G2 are independently a hydrogen atom, a nitro group (—NO2), a halogen atom, a cyano group (—CN), a group of formula (II) or (III), or both G1 and G2 taken together to form a group of formula (IV).

Abstract: Described herein are methods of syntheses of phosphorous atom-modified nucleic acids comprising chiral X-phosphonate moieties. The methods described herein provide backbone-modified nucleic acids in high diasteteomeric purity via an asymmetric reaction of an achiral molecule comprising a chemically stable H-phophonate moiety with a nucleoside/nucleotide.