Enzymatic synthesis of biphenyl-DNA oligonucleotides

Röthlisberger, Pascal; Levi-Acobas, Fabienne; Leumann, Christian J.; Hollenstein, Marcel (2020). Enzymatic synthesis of biphenyl-DNA oligonucleotides. Bioorganic & medicinal chemistry, 28(11), p. 115487. Elsevier 10.1016/j.bmc.2020.115487

[img] Text
1-s2.0-S0968089620303084-main.pdf - Published Version
Restricted to registered users only
Available under License Publisher holds Copyright.

Download (1MB) | Request a copy

The incorporation of nucleotides equipped with C-glycosidic aromatic nucleobases into DNA and RNA is an alluring strategy for a number of practical applications including fluorescent labelling of oligonucleotides, expansion of the genetic alphabet for the generation of aptamers and semi-synthetic organisms, or the modulation of excess electron transfer within DNA. However, the generation of C-nucleoside containing oligonucleotides relies mainly on solid-phase synthesis which is quite labor intensive and restricted to short sequences. Here, we explore the possibility of constructing biphenyl-modified DNA sequences using enzymatic synthesis. The presence of multiple biphenyl-units or biphenyl residues modified with electron donors and acceptors permits the incorporation of a single dBphMP nucleotide. Moreover, templates with multiple abasic sites enable the incorporation of up to two dBphMP nucleotides, while TdT-mediated tailing reactions produce single-stranded DNA oligonucleotides with four biphenyl residues appended at the 3′-end.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Departement of Chemistry and Biochemistry

UniBE Contributor:

Leumann, Christian

Subjects:

500 Science > 570 Life sciences; biology
500 Science > 540 Chemistry

ISSN:

0968-0896

Publisher:

Elsevier

Language:

English

Submitter:

Christian Leumann

Date Deposited:

08 Jun 2020 17:10

Last Modified:

08 Jun 2020 17:10

Publisher DOI:

10.1016/j.bmc.2020.115487

PubMed ID:

32284226

Uncontrolled Keywords:

DNA polymerases Modified nucleic acids Nucleoside triphosphates Biaryls Hydrophobic bases

BORIS DOI:

10.7892/boris.144121

URI:

https://boris.unibe.ch/id/eprint/144121

Actions (login required)

Edit item Edit item
Provide Feedback