Bicyclo[3.2.1]amide-DNA: a chiral, non-chiroselective base-pairing system

Ahn, D. R.; Egger, A.; Lehmann, C.; Pitsch, S.; Leumann, Christian (2002). Bicyclo[3.2.1]amide-DNA: a chiral, non-chiroselective base-pairing system. Chemistry - a European journal, 8(23), pp. 5312-5322. Wiley-VCH 10.1002/1521-3765(20021202)8:23<5312::AID-CHEM5312>3.0.CO;2-M

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The design, synthesis and base-pairing properties of bicyclo[3.2.1]amide-(bca)DNA, a novel phosphodiester based DNA analogue, is reported. This analogue consists of a conformationally constrained backbone entity which emulates a B-DNA geometry, to which the nucleobases were attached via an extended, acyclic amide linker. Homobasic adenine-containing bca-decamers form duplexes with complementary oligonucleotides containing the bca-, the DNA the RNA and, surprisingly, also the L-RNA backbone. UV- and CD-spectroscopic investigations revealed the duplexes with D- or L-complement to be of similar stability and enantiomorphic in structure. Bca-oligonucleotides containing all four bases form strictly antiparallel, left-handed complementary duplexes with itself and complementary DNA but not with RNA. Base-mismatch discrimination is comparable to that of DNA while the overall thermal stabilities of bca-oligonucleotide duplexes are inferior relative to that of DNA or RNA. A detailed molecular modeling study of left- and right-handed bca-DNA containing duplexes showed only minor changes in the backbone structure and revealed a structural switch around the base-linker unit to be responsible for the generation of enantiomorphic duplex structures. The obtained data are discussed with respect to the structural and energetic role of the ribofuranose entities in DNA and RNA association

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:

0947-6539

Publisher:

Wiley-VCH

Language:

English

Submitter:

Christian Leumann

Date Deposited:

19 May 2015 10:37

Last Modified:

19 May 2015 10:37

Publisher DOI:

10.1002/1521-3765(20021202)8:23<5312::AID-CHEM5312>3.0.CO;2-M

PubMed ID:

12432499

Uncontrolled Keywords:

acyclic amide analogue antiparallel backbone base Base Pairing BASE-PAIRING PROPERTIES bases change data DNA duplex DUPLEXES linker molecular molecular modeling nucleobases oligonucleotide Oligonucleotides properties RNA stability Structure switch synthesis thermal

BORIS DOI:

10.7892/boris.68584

URI:

https://boris.unibe.ch/id/eprint/68584

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