Synthesis of a cyclopentane amide DNA analogue and its base pairing properties

Ahn, D. R.; Mosimann, Markus; Leumann, Christian (2003). Synthesis of a cyclopentane amide DNA analogue and its base pairing properties. Nucleosides, nucleotides & nucleic acids, 22(5-8), pp. 1207-1210. Taylor & Francis 10.1081/NCN-120022837

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cpa-DNA monomers containing the bases adenine and thymine have been synthesized starting from the known compound 1 in 12 steps. Partially and fully modified cpa-thymidine and cpa-adenosine containing oligodeoxynucleotides were synthesized by standard oligonucleotide chemistry. Fully modified homo-cpa-A sequences lead to duplex destabilization by -1.4 degrees C/mod. relative to DNA. As its congener bca-DNA, cpa-DNA prefers left-handed duplex formation where possible

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP)

UniBE Contributor:

Mosimann, Markus (A), Leumann, Christian

Subjects:

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

ISSN:

1525-7770

Publisher:

Taylor & Francis

Language:

English

Submitter:

Christian Leumann

Date Deposited:

19 May 2015 08:19

Last Modified:

29 Mar 2023 23:34

Publisher DOI:

10.1081/NCN-120022837

Additional Information:

Notes: Department of Chemistry and Biochemistry, University of Bern, Bern, SwitzerlandFAU - Ahn, Dae-Ro

Uncontrolled Keywords:

adenine amide Amides analogue base Base Pairing Base Sequence bases chemistry Circular Dichroism Cyclopentanes DNA duplex DUPLEXES Indicators and Reagents modified monomers Nucleic Acid Conformation Oligodeoxynucleotides OLIGODEOXYRIBONUCLEOTIDES oligonucleotide PAIRING PROPERTIES properties Structure-Activity Relationship synthesis THYMINE

BORIS DOI:

10.7892/boris.68575

URI:

https://boris.unibe.ch/id/eprint/68575

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