UNIT 4.24 Oligodeoxyribonucleotide Analogs Functionalized with Phosphonoacetate and Thiophosphonoacetate Diesters
Published Online: 1 OCT 2004
Copyright © 2003 by John Wiley and Sons, Inc.
Lab Protocol Title
Current Protocols in Nucleic Acid Chemistry
How to Cite
Dellinger, D. J., Yamada, C. M. and Caruthers, M. H. 2004. Oligodeoxyribonucleotide Analogs Functionalized with Phosphonoacetate and Thiophosphonoacetate Diesters. Current Protocols in Nucleic Acid Chemistry. 18:4.24:4.24.1–4.24.26.
- Published Online: 1 OCT 2004
- Published Print: SEP 2004
Oligodeoxyribonucleotides with phosphonoacetate or thiophosphonoacetate internucleotide linkages can be made in high yield by solid-phase synthesis and possess many advantages. They are highly stable to nucleases, water-soluble, and anionic at neutral pH. They form stable duplexes with DNA and RNA, and stimulate RNase H degradation of complementary RNA. The preparation of the N,N-(diisopropylamino)phosphinyl acetate monomers from standard protected nucleosides is described here, followed by the synthesis of phosphonoacetate and thiophosphonoate oligodeoxyribonucleotides, as well as chimeric oligomers that have these modified linkages in combination with natural or phosphorothioate linkages. Purification and characterization of these oligomers is also presented.
- phosphonoacetate DNA synthesis;
- thiophosphonoacetate DNA synthesis