O-Acetyl Side-Chains in Monosaccharides: Redundant NMR Spin-Couplings and Statistical Models for Acetate Ester Conformational Analysis.

ABSTRACT: α- and β-d-glucopyranose monoacetates 1-3 were prepared with selective ¹³C enrichment in the O-acetyl side-chain, and ensembles of ¹³C-¹H and ¹³C-¹³C NMR spin-couplings (J-couplings) were measured involving the labeled carbons. Density functional theory (DFT) was applied to a set of model structures to determine which J-couplings are sensitive to rotation of the ester bond θ. Eight J-couplings (¹J_CC, ²J_CH, ²J_CC, ³J_CH, and ³J_CC) were found to be sensitive to θ, and four equations were parametrized to allow quantitative interpretations of experimental J-values. Inspection of J-coupling ensembles in 1-3 showed that O-acetyl side-c

SUBMITTER: Turney T 

PROVIDER: S-EPMC5556682 | biostudies-literature | 2017 Jan

REPOSITORIES: biostudies-literature