A novel approach to oligodeoxyribonucleotides bearing phosphoric acid esters at the 3'-terminals via the phosphoramidite method with allyl protection: An efficient synthesis of base-labile nucleotide-amino acid and - peptide conjugates

Akira Sakakura; Yoshihiro Hayakawa; Hitoshi Harada; Masaaki Hirose; Ryoji Noyori

doi:10.1016/S0040-4039(99)00748-0

A novel approach to oligodeoxyribonucleotides bearing phosphoric acid esters at the 3'-terminals via the phosphoramidite method with allyl protection: An efficient synthesis of base-labile nucleotide-amino acid and - peptide conjugates

Akira Sakakura, Yoshihiro Hayakawa, Hitoshi Harada, Masaaki Hirose, Ryoji Noyori

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

A new method for synthesis of 3'-end-phosphorylated DNA oligomers via the phosphoramidite method with allyl protection has been developed. This method is particularly useful for the preparation of derivatives with base- labile structures such as oligoDNA-OPO(OH)OCH₂CH(R)Z, in which Z is an electron-withdrawing function. For example, a oligonucleotide-amino acid conjugate, ⁵'TGTCGACACCCAATT³'-OPO(OH)OCH₂CH(NH₂)COOH, and a oligonucleotide-peptide conjugate, ⁵'TGTCGACACCCAATT³'- OPO(OH)OCH₂CH(NH₂)CONHCH₂COOH, have been obtained in high purity.

Original language	English
Pages (from-to)	4359-4362
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	23
DOIs	https://doi.org/10.1016/S0040-4039(99)00748-0
Publication status	Published - Jun 4 1999
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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Sakakura, A., Hayakawa, Y., Harada, H., Hirose, M., & Noyori, R. (1999). A novel approach to oligodeoxyribonucleotides bearing phosphoric acid esters at the 3'-terminals via the phosphoramidite method with allyl protection: An efficient synthesis of base-labile nucleotide-amino acid and - peptide conjugates. Tetrahedron Letters, 40(23), 4359-4362. https://doi.org/10.1016/S0040-4039(99)00748-0

A novel approach to oligodeoxyribonucleotides bearing phosphoric acid esters at the 3'-terminals via the phosphoramidite method with allyl protection: An efficient synthesis of base-labile nucleotide-amino acid and - peptide conjugates. / Sakakura, Akira; Hayakawa, Yoshihiro; Harada, Hitoshi et al.
In: Tetrahedron Letters, Vol. 40, No. 23, 04.06.1999, p. 4359-4362.

Research output: Contribution to journal › Article › peer-review

Sakakura, A, Hayakawa, Y, Harada, H, Hirose, M & Noyori, R 1999, 'A novel approach to oligodeoxyribonucleotides bearing phosphoric acid esters at the 3'-terminals via the phosphoramidite method with allyl protection: An efficient synthesis of base-labile nucleotide-amino acid and - peptide conjugates', Tetrahedron Letters, vol. 40, no. 23, pp. 4359-4362. https://doi.org/10.1016/S0040-4039(99)00748-0

Sakakura A, Hayakawa Y, Harada H, Hirose M, Noyori R. A novel approach to oligodeoxyribonucleotides bearing phosphoric acid esters at the 3'-terminals via the phosphoramidite method with allyl protection: An efficient synthesis of base-labile nucleotide-amino acid and - peptide conjugates. Tetrahedron Letters. 1999 Jun 4;40(23):4359-4362. doi: 10.1016/S0040-4039(99)00748-0

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title = "A novel approach to oligodeoxyribonucleotides bearing phosphoric acid esters at the 3'-terminals via the phosphoramidite method with allyl protection: An efficient synthesis of base-labile nucleotide-amino acid and - peptide conjugates",

abstract = "A new method for synthesis of 3'-end-phosphorylated DNA oligomers via the phosphoramidite method with allyl protection has been developed. This method is particularly useful for the preparation of derivatives with base- labile structures such as oligoDNA-OPO(OH)OCH2CH(R)Z, in which Z is an electron-withdrawing function. For example, a oligonucleotide-amino acid conjugate, 5'TGTCGACACCCAATT3'-OPO(OH)OCH2CH(NH2)COOH, and a oligonucleotide-peptide conjugate, 5'TGTCGACACCCAATT3'- OPO(OH)OCH2CH(NH2)CONHCH2COOH, have been obtained in high purity.",

author = "Akira Sakakura and Yoshihiro Hayakawa and Hitoshi Harada and Masaaki Hirose and Ryoji Noyori",

note = "Funding Information: Acknowledgment. The author (Y.H.) acknowledges partial supports by Grants-in-Aid for Scientific Research (Nos. 08454200, 10169225, and 10554042) from the Ministry of Education, Science, Sports and Culture, by a grant from the {"}Research for the Future{"} Program of the Japan Society for the Promotion of Science (JSPS-RFTF97100301), and by the Asahi Glass Foundation and the Daiko Foundation.",

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doi = "10.1016/S0040-4039(99)00748-0",

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AU - Sakakura, Akira

AU - Hayakawa, Yoshihiro

AU - Harada, Hitoshi

AU - Hirose, Masaaki

AU - Noyori, Ryoji

N1 - Funding Information: Acknowledgment. The author (Y.H.) acknowledges partial supports by Grants-in-Aid for Scientific Research (Nos. 08454200, 10169225, and 10554042) from the Ministry of Education, Science, Sports and Culture, by a grant from the "Research for the Future" Program of the Japan Society for the Promotion of Science (JSPS-RFTF97100301), and by the Asahi Glass Foundation and the Daiko Foundation.

PY - 1999/6/4

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N2 - A new method for synthesis of 3'-end-phosphorylated DNA oligomers via the phosphoramidite method with allyl protection has been developed. This method is particularly useful for the preparation of derivatives with base- labile structures such as oligoDNA-OPO(OH)OCH2CH(R)Z, in which Z is an electron-withdrawing function. For example, a oligonucleotide-amino acid conjugate, 5'TGTCGACACCCAATT3'-OPO(OH)OCH2CH(NH2)COOH, and a oligonucleotide-peptide conjugate, 5'TGTCGACACCCAATT3'- OPO(OH)OCH2CH(NH2)CONHCH2COOH, have been obtained in high purity.

AB - A new method for synthesis of 3'-end-phosphorylated DNA oligomers via the phosphoramidite method with allyl protection has been developed. This method is particularly useful for the preparation of derivatives with base- labile structures such as oligoDNA-OPO(OH)OCH2CH(R)Z, in which Z is an electron-withdrawing function. For example, a oligonucleotide-amino acid conjugate, 5'TGTCGACACCCAATT3'-OPO(OH)OCH2CH(NH2)COOH, and a oligonucleotide-peptide conjugate, 5'TGTCGACACCCAATT3'- OPO(OH)OCH2CH(NH2)CONHCH2COOH, have been obtained in high purity.

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A novel approach to oligodeoxyribonucleotides bearing phosphoric acid esters at the 3'-terminals via the phosphoramidite method with allyl protection: An efficient synthesis of base-labile nucleotide-amino acid and - peptide conjugates

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