Efficient synthesis of functionalized oligodeoxyribonucleotides with base-labile groups using a new silyl linker

Akihiro Ohkubo; Rintaro Kasuya; Katsufumi Aoki; Akio Kobori; Haruhiko Taguchi; Kohji Seio; Mitsuo Sekine

doi:10.1016/j.bmc.2008.02.076

Efficient synthesis of functionalized oligodeoxyribonucleotides with base-labile groups using a new silyl linker

Bioorg Med Chem. 2008 May 1;16(9):5345-51. doi: 10.1016/j.bmc.2008.02.076. Epub 2008 Feb 29.

Authors

Akihiro Ohkubo¹, Rintaro Kasuya, Katsufumi Aoki, Akio Kobori, Haruhiko Taguchi, Kohji Seio, Mitsuo Sekine

Affiliation

¹ Department of Life Science, Tokyo Institute of Technology and CREST, JST (Japan Science and Technology Agency), Japan.

PMID: 18439833
DOI: 10.1016/j.bmc.2008.02.076

Abstract

In this study, we developed new 3'-terminal deoxyribonucleoside-loading reagents 1 with a new silyl-type linker. These reagents could increase the efficiency of introduction of 3'-terminal deoxyribonucleoside components into polymer supports to a level of 17-29micromol/g. The efficiency was higher than that of previous T-loading reagents because reagents 1 contain a 4-aminobutyryl residue as a spacer. Moreover, we could synthesize not only unmodified DNA oligomers but also a base-labile modified DNA oligomer using resins 9a-d in the activated phosphite method without base protection.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Molecular Structure
Oligodeoxyribonucleotides / chemical synthesis*
Oligodeoxyribonucleotides / chemistry
Silanes / chemical synthesis
Silanes / chemistry*
Stereoisomerism

Substances

Oligodeoxyribonucleotides
Silanes