Watson-Crick base-pairing properties of tricyclo-DNA

Renneberg, Dorte; Leumann, Christian (2002). Watson-Crick base-pairing properties of tricyclo-DNA. Journal of the American Chemical Society, 124(21), pp. 5993-6002. American Chemical Society 10.1021/ja025569+

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Tricyclo-DNA belongs to the family of conformationally restricted oligodeoxynucleotide analogues. It differs structurally from DNA by an additional ethylene bridge between the centers C(3') and C(5') of the nucleosides, to which a cyclopropane unit is fused for further enhancement of structural rigidity. The synthesis of the hitherto unknown tricyclodeoxynucleosides containing the bases cytosine and guanine and of the corresponding phosphoramidite building blocks is described, as well as a structural description of a representative of an alpha- and a beta-tricyclodeoxynucleoside by X-ray analysis. Tricyclodeoxynucleoside building blocks of all four bases were used for the synthesis of fully modified mixed-base oligonucleotides. Their Watson-Crick pairing properties with complementary DNA, RNA, and with itself were investigated by UV melting curves, CD spectroscopy, and molecular modeling. Tricyclo-DNA was found to be a very stable Watson-Crick base-pairing system. A UV melting curve analysis of the decamers tcd(pcgtgacagtt) and tcd(paactgtcacg) showed increased thermal stabilities of up to DeltaT(m)/mod. = +1.2 degrees C with complementary DNA and +2.4 degrees C with complementary RNA. With itself, tricyclo-DNA showed an increase in stability of +3.1 degrees C/base pair relative to DNA. Investigations into the thermodynamic properties of these decamers revealed an entropic stabilization and an enthalpic destabilization for the tricyclo-DNA/DNA duplexes. CD spectroscopic structural investigations indicated that tricyclo-DNA containing duplexes preferrably exist in an A-conformation, a fact which is in agreement with results from molecular modeling

Item Type:

Journal Article (Original Article)


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

UniBE Contributor:

Renneberg, Dorte, Leumann, Christian


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




American Chemical Society




Christian Leumann

Date Deposited:

19 May 2015 12:41

Last Modified:

05 Dec 2022 14:46

Publisher DOI:


PubMed ID:


Uncontrolled Keywords:

analogue analogues analysis base Base Pairing BASE-PAIRING PROPERTIES bases CD conformationally restricted Cytosine DNA duplex DUPLEXES Guanine modified molecular molecular modeling nucleoside nucleosides oligonucleotide Oligonucleotides PAIRING PROPERTIES phosphoramidite properties RNA stability synthesis thermal thermodynamic tricyclo-DNA X-ray





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