Proton magnetic resonance studies of 2′-deoxynucleosides and nucleotides in the syn conformation
Keyword(s):
Proton magnetic resonance data for 6-methyl-2′-deoxyuridine and its 3′- and 5′-monophosphate derivatives are obtained in aqueous solution and compared with data for corresponding thymine derivatives. The data show that the derivatives of the 6-methyluracil base occupy the syn conformation. The presence of the syn base leads to a flattening of the sugar ring and destabilization of the g+ conformer about the C(4′)—C(5′) bond. This destabilization is particularly large at the 5′-nucleotide level and is discussed in terms of a repulsive interaction involving the 2-keto oxygen of the base and the negatively charged 5′-group.
1968 ◽
Vol 46
(12)
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pp. 2071-2074
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1967 ◽
Vol 71
(12)
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pp. 3954-3959
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1970 ◽
Vol 40
(1)
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pp. 179-185
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1968 ◽
Vol 90
(17)
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pp. 4583-4585
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1993 ◽
Vol 28
(5-6)
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pp. 329-332
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1973 ◽
Vol 51
(15)
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pp. 2571-2577
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1965 ◽
Vol 6
(50)
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pp. 4515-4522
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