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Ah Sugar, Sugar … Residue

Sugar residues (saccharides) can be tough to elucidate. They tend to have 1H NMR spectrum with overlapping and sometimes poorly-resolved 1H signals, and the 2D NMR data presents lots of ambiguous assignments. With a little practice, an elucidator can quickly pick out a sugar moiety based on a minimal amount of NMR data.

For a given set of atoms with known 13C chemical shifts (shown below), a hexopyranoside sugar moiety is evident even without any long-range coupling information. The general pattern is as follows: a CH at ~100 ppm, 4 CHs between ~70 to 77 ppm, a CH2 at ~60 ppm, 6 O atoms and 4 H atoms. Note: the H atoms count may vary depending on the number of connection points.

SugarNMR_Atoms_Feb232010

 

An example sugar, phenyl hexapyranoside, with 13C chemical shifts is presented below.

SugarNMR_Str_Feb232010

 

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