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Synthesis and solution conformation studies of 3-substituted uridine and pseudouridine derivatives.

ABSTRACT: A series of 3-substituted uridine and pseudouridine derivatives, based on the naturally occurring 3-(3-amino-3-carboxypropyl) modification, were synthesized. Their aqueous solution conformations were determined by using circular dichroism and NMR spectroscopy. Functional group composition and chain length were shown to have only a subtle influence on the distribution of syn/anti conformations of the modified nucleosides. The dominating factor appears to be the glycosidic linkage (C- vs. N-glycoside) in determining the nucleoside conformation.

SUBMITTER: Chang YC

PROVIDER: S-EPMC2295217 | biostudies-literature | 2008 Mar

REPOSITORIES: biostudies-literature

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Synthesis and solution conformation studies of 3-substituted uridine and pseudouridine derivatives.

Chang Yu-Cheng YC Herath Jayatilake J Wang Tony H-H TH Chow Christine S CS

Bioorganic & medicinal chemistry 20071119 5

A series of 3-substituted uridine and pseudouridine derivatives, based on the naturally occurring 3-(3-amino-3-carboxypropyl) modification, were synthesized. Their aqueous solution conformations were determined by using circular dichroism and NMR spectroscopy. Functional group composition and chain length were shown to have only a subtle influence on the distribution of syn/anti conformations of the modified nucleosides. The dominating factor appears to be the glycosidic linkage (C- vs. N-glycos ...[more]

PMID: 18078759

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