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 -peptideconjugates

Authors
Sakakura, A Hayakawa, Y Harada, H Hirose, M Noyori, R
Citation
A. Sakakura et al., 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 -peptideconjugates, TETRAHEDR L, 40(23), 1999, pp. 4359-4362
Citations number
24
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
23
Year of publication
1999
Pages
4359 - 4362
Database
ISI
SICI code
0040-4039(19990604)40:23<4359:ANATOB>2.0.ZU;2-A
Abstract
A new method for synthesis of 3'-end-phosphorylated DNA oligomers via the p hosphoramidite 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-w ithdrawing function. For example, a oligonucleotide-amino acid conjugate, ( 5)'TGTCGACACCCAATT(3)'-OPO(OH)OCH2CH(NH2)COOH, and a oligonucleotide-peptid e conjugate, (5)'TGTCGACA-CCCAATT(3)'-OPO(OH)OCH2CH(NH2)CONHCH2COOH, have b een obtained in high purity. (C) 1999 Elsevier Science Ltd. All rights rese rved.