Investigation of the torsional angle at the glycosidic bond in 5′-amino-5′-deoxythymidine derivatives by carbon-13 n.m.r. spectroscopy
✍ Scribed by Eileen M. Nottoli; Joseph B. Lambert; Robert L. Letsinger
- Publisher
- John Wiley and Sons
- Year
- 1977
- Tongue
- English
- Weight
- 426 KB
- Volume
- 9
- Category
- Article
- ISSN
- 0749-1581
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✦ Synopsis
Abstract
The conformational preference of the thymine base ring with respect to the sugar ring in β,β,β,‐trichloroethyl 5′amino‐5′‐deoxythymidine‐5′‐phosphate has been studied by ^13^C n.m.r. spectroscopy. The magnitude of the three bond vicinal coupling constant, J(C‐2, H‐1′), for β,β,β‐trichloroethyl 5′‐amino‐5′‐deoxythymidine‐5′‐phosphate and the similarity between the chemical shifts for the furanose carbons C‐1′, C‐2′, and C‐3′ in β,β,β‐trichloroethyl 5‐′‐amino‐5′‐deoxythymidine‐5′‐phosphate and in β,β,β‐trichloroethyl thymidine 5′‐phosphate indicate that the amino analogue exists in aqueous solution predominantly in the anti conformation, as is the case with natural nucleotides.