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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

✍ Scribed by Akira Sakakura; Yoshihiro Hayakawa; Hitoshi Harada; Masaaki Hirose; Ryoji Noyori


Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
266 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis


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'TGTCGACA-CCCAATT3'-OPO(OH)OCH2CH(NH2)CONHCH2COOH, have been obtained in high purity.