Screening the Structural Space of Bicyclo-DNA: Synthesis and Properties of Bicyclo-DNA Functionalized at C(6’)

Luisier, Samuel; Leumann, Christian J. (2010). Screening the Structural Space of Bicyclo-DNA: Synthesis and Properties of Bicyclo-DNA Functionalized at C(6’). Heterocycles, 82(1), pp. 775-790. Amsterdam: Elsevier Science 10.3987/com-10-s(e)65

[img] Text
Heterocycles 2010, 82, 775.pdf - Published Version
Restricted to registered users only
Available under License Publisher holds Copyright.

Download (1MB) | Request a copy

The synthesis of a novel bicyclo-thymidine nucleoside bearing an ester functionality at C(6') (bc(alpha-alk)-nucleosides) is reported. This nucleoside was incorporated into oligodeoxynucleotides via solid phase phosphoramidite chemistry, and the ester moiety was post-synthetically converted to an amide or a carboxy group, or was left unchanged. Thermal melting data (T-m) with complementary DNA and RNA were collected and compared to natural DNA and to bc- and bc(ox)-DNA. It was found that single incorporations of bc(alpha-alk)-nucleosides in DNA duplexes were destabilizing by 0.5 to 2.5 degrees C/mod, whereas two consecutive bc(alpha-alk)-residues were less destabilizing, and in some cases even stabilizing by 0.5 degrees C/mod. In duplexes with complementary RNA, isolated bc(alpha-alk)-residues destabilized the duplex by -1.0 to -4.0 degrees C/mod, depending on the chemical nature of the substituent, whereas two consecutive modifications were only destabilizing by 0.3-1.0 degrees C/mod. The pairing selectivity was similar to that of unmodified or bc-DNA.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Departement of Chemistry and Biochemistry

UniBE Contributor:

Luisier, Samuel and Leumann, Christian

Subjects:

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

ISSN:

0385-5414

ISBN:

0385-5414

Publisher:

Elsevier Science

Language:

English

Submitter:

Christian Leumann

Date Deposited:

04 Oct 2013 14:17

Last Modified:

10 Aug 2015 11:12

Publisher DOI:

10.3987/com-10-s(e)65

Web of Science ID:

000286906100052

BORIS DOI:

10.7892/boris.5184

URI:

https://boris.unibe.ch/id/eprint/5184 (FactScience: 209908)

Actions (login required)

Edit item Edit item
Provide Feedback