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  NAA-modified DNA oligonucleotides with zwitterionic backbones: stereoselective synthesis of A-T phosphoramidite building blocks.

Schmidtgall, B., Höbartner, C., & Ducho, C. (2015). NAA-modified DNA oligonucleotides with zwitterionic backbones: stereoselective synthesis of A-T phosphoramidite building blocks. Beilstein Journal of Organic Chemistry, 11, 50-60. doi:10.3762/bjoc.11.8.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-0025-0605-C Version Permalink: http://hdl.handle.net/11858/00-001M-0000-002A-19A7-D
Genre: Journal Article

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 Creators:
Schmidtgall, B., Author
Höbartner, C.1, Author              
Ducho, C., Author
Affiliations:
1Research Group of Nucleic Acid Chemistry, MPI for biophysical chemistry, Max Planck Society, ou_578605              

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Free keywords: backbone modifications; DNA; nucleic acids; oligonucleotides; stereoselective synthesis; zwitterions
 Abstract: Modifications of the nucleic acid backbone are essential for the development of oligonucleotide-derived bioactive agents. The NAA-modification represents a novel artificial internucleotide linkage which enables the site-specific introduction of positive charges into the otherwise polyanionic backbone of DNA oligonucleotides. Following initial studies with the introduction of the NAA-linkage at T-T sites, it is now envisioned to prepare NAA-modified oligonucleotides bearing the modification at X-T motifs (X = A, C, G). We have therefore developed the efficient and stereoselective synthesis of NAA-linked 'dimeric' A-T phosphoramidite building blocks for automated DNA synthesis. Both the (S)- and the (R)-configured NAA-motifs were constructed with high diastereoselectivities to furnish two different phosphoramidite reagents, which were employed for the solid phase-supported automated synthesis of two NAA-modified DNA oligonucleotides. This represents a significant step to further establish the NAA-linkage as a useful addition to the existing 'toolbox' of backbone modifications for the design of bioactive oligonucleotide analogues.

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Language(s): eng - English
 Dates: 2015-01-13
 Publication Status: Published online
 Pages: -
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 Table of Contents: -
 Rev. Method: Peer
 Identifiers: DOI: 10.3762/bjoc.11.8
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Title: Beilstein Journal of Organic Chemistry
Source Genre: Journal
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Pages: - Volume / Issue: 11 Sequence Number: - Start / End Page: 50 - 60 Identifier: -