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Oligonucleotide Analogues with Integrated Bases and Backbone. Part 16 : Synthesis and Association of Ethylene-Linked Self-Complementary Dimers

✍ Scribed by Xiaomin Zhang; Bruno Bernet; Andrea Vasella

Publisher
John Wiley and Sons
Year
2007
Tongue
German
Weight
331 KB
Volume
90
Category
Article
ISSN
0018-019X

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✦ Synopsis

The self-complementary, ethylene-linked U*[c a ]A ( * ) dinucleotide analogues 8, 10, 12, 14, 16, and 18, and the sequence-isomeric A*[c a ]U ( * ) analogues 20, 22, 24, 26, 28, and 30 were obtained by Pd/Ccatalyzed hydrogenation of the corresponding, known ethynylene-linked dimers. The association of the ethylene-linked dimers was investigated by NMR and CD spectroscopy. The U*[c a ]A ( * ) dimers form linear duplexes and higher associates (K between 29 and 114m Γ€1 ). The A*[c a ]U ( * ) dimers, while associating more strongly (K between 88 and 345m Γ€1 ), lead mostly to linear duplexes and higher associates; they form only minor amounts of cyclic duplexes. The enthalpy -entropy compensation characterizing the association of the U*[c x ]A ( * ) and A*[c x ]U ( * ) dimers (x ΒΌ y, e, and a) is discussed.

πŸ“œ SIMILAR VOLUMES

Oligonucleotide Analogues with Integrate
Oligonucleotide Analogues with Integrated Bases and Backbone. Part 15 : Synthesis and Association of Ethenylene-Linked Self-Complementary Dimers
✍ Xiaomin Zhang; Bruno Bernet; Andrea Vasella πŸ“‚ Article πŸ“… 2007 πŸ› John Wiley and Sons 🌐 German βš– 510 KB

The self-complementary (Z)-configured U\*[c e ]A ( \* ) dinucleotide analogues 6, 8, 10, 12, 14, and 16, and the A\*[c e ]U ( \* ) dimers 19, 21, 23, 25, 27, and 29 were prepared by partial hydrogenation of the corresponding ethynylene linked dimers. Photolysis of 14 led to the (E)-alkene 17. These

Oligonucleotide Analogues with Integrate
Oligonucleotide Analogues with Integrated Bases and Backbone. Part 14 : Synthesis and Association of Ethynylene-Linked Self-Complementary Tetramers
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## Abstract The self‐complementary tetrameric propargyl triols **8, 14, 18**, and **21** were synthesized to investigate the duplex formation of self‐complementary, ethynylene‐linked UUAA, AAUU, UAUA, and AUAU analogues with integrated bases and backbone (ONIBs). The linear synthesis is based on re

Oligonucleotide Analogues with Integrate
Oligonucleotide Analogues with Integrated Bases and Backbone. Part 17 : Conformational Analysis and Association of Ethylene-, Oxymethylene-, and Thiomethylene-Linked Self-Complementary Adenosine and Uridine Dimers
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The formation of cyclic duplexes (pairing) of known oxymethylene-linked self-complementary U\*[o]A ( \* ) dinucleosides contrasts with the absence of pairing of the ethylene-linked U\*[c a ]A ( \* ) analogues. The origin of this difference, and the expected association of U\*[x]A ( \* ) and A\*[x]U