Parallel synthesis and nucleic acid binding properties of C(6')-[alpha]-functionalized bicyclo-DNA

Silhár, Peter; Leumann, Christian J. (2010). Parallel synthesis and nucleic acid binding properties of C(6')-[alpha]-functionalized bicyclo-DNA. Bioorganic & medicinal chemistry, 18(22), pp. 7786-7793. Amsterdam: Elsevier 10.1016/j.bmc.2010.09.064

[img] Text
BMC8753.pdf - Published Version
Restricted to registered users only
Available under License Publisher holds Copyright.

Download (686kB) | Request a copy

Two novel bicyclo-T nucleosides carrying a hydroxyl or a carboxymethyl substituent in C(6')-[alpha]-position were prepared and incorporated into oligodeoxynucleotides. During oligonucleotide deprotection the carboxymethyl substituent was converted into different amide substituents in a parallel way. Tm-measurements showed no dramatic differences in both, thermal affinity and mismatch discrimination, compared to unmodified oligonucleotides. The post-synthetic modification of the carboxymethyl substituent allows in principle for a parallel preparation of a library of oligonucleotides carrying diverse substituents at C(6'). In addition, functional groups can be placed into unique positions in a DNA double helix.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Departement of Chemistry and Biochemistry

UniBE Contributor:

Silhar, Peter and Leumann, Christian

Subjects:

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

ISSN:

0968-0896

ISBN:

0968-0896

Publisher:

Elsevier

Language:

English

Submitter:

Christian Leumann

Date Deposited:

04 Oct 2013 14:17

Last Modified:

10 Aug 2015 11:11

Publisher DOI:

10.1016/j.bmc.2010.09.064

Web of Science ID:

000283649900010

BORIS DOI:

10.7892/boris.5185

URI:

https://boris.unibe.ch/id/eprint/5185 (FactScience: 209909)

Actions (login required)

Edit item Edit item
Provide Feedback