## 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
Oligonucleotide Analogues with Integrated Bases and Backbones. Part 23 : Conformational Analysis and Association of Sulfonyl- and Sulfinylmethylene Adenosine and Uridine Dinucleosides
✍ Scribed by Nicolas Bogliotti; Bruno Bernet; Andrea Vasella
- Publisher
- John Wiley and Sons
- Year
- 2010
- Tongue
- German
- Weight
- 269 KB
- Volume
- 93
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
The sulfone 2, and the sulfoxides (S)‐3 and (R)‐3 were obtained by oxidation of the thiomethylene‐linked A*[s]U dinucleoside 1. Conformational analysis and association studies of 2, (S)‐3, and (R)‐3 reveal a strong influence of the configuration on the conformation of the linking unit and on the self‐association of the dinucleosides.
📜 SIMILAR VOLUMES
## 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
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
The (chloromethyl)cytidine 7 was obtained from alcohol 4 that was synthesized from the protected cytidine 3 by C(6)-formylation and reduction. Thioacetate 10 was obtained from the cytidine 2, and thioacetate 8 from a Mitsunobu reaction of alcohol 6. The thiomethylene-linked dinucleoside 11 was synth
## 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