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Oligonucleotide Analogues with Integrated Bases and Backbones. Part 25 : Structural Effects on the Gelation of Self-Complementary A*[s]U Dinucleosides

✍ Scribed by Nicolas Bogliotti; Andrea Vasella

Publisher
John Wiley and Sons
Year
2010
Tongue
German
Weight
578 KB
Volume
93
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The ability of A*[s]U dinucleosides to gel organic solvents and water is modulated by changing the nature of the substituents at __O__C(2′) and __O__C(3′), as evidenced by comparing the gelation of the dinucleosides 7–9 and the properties of the gels. A mere extension of the hydrophobic moiety, by replacing the isopropylidene groups of 2 by cyclohexylidene groups, as in 7, has a small effect, while changing the conformation of the ribose ring and reducing the size of the hydrophobic moiety, as in 8, has a strong effect on the scope of gelation, the minimum gelation concentration, as low as 0.07% for pentanol and decanol, and the properties of the gel. The fully deprotected dinucleoside 9 gels water at a minimal gelation concentration of 0.6%. A TEM of the corresponding xerogel shows the formation of fibers with a diameter of ca. 30 to 90 nm.

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Oligonucleotide Analogues with Integrate
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## Abstract Inspection of __Maruzen__ models and force‐field calculations suggest that oligonucleotide analogues integrating backbone and bases (ONIBs) with an aminomethylene linker form similar cyclic duplexes as the analogous oxymethylene linked dinucleosides. The self‐complementary adenosine‐ an

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## Abstract The self‐complementary aminomethylene‐linked A\*[n]U\* dinucleosides **23**–**26** were prepared by reductive coupling of aldehyde **10** and azide **8**. The U\*[n]A\* sequence isomers **19**–**21** were similarly prepared from aldehyde **14** and azide **3**. The substituents at C(6/I