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. Author manuscript; available in PMC: 2009 Mar 29.
Published in final edited form as: J Am Chem Soc. 2006 Sep 20;128(37):12221–12228. doi: 10.1021/ja063651p

Figure 5.

Figure 5

Expansion of the 1H NMR spectra of solutions of (a) D-ribose and (b) a mixture of 1 and D-ribose (0.15 M NaOD/D2O). The resonances shown correspond the anomeric protons of each of the four cyclic forms. The assignments are δ (ppm): 5.30 (α-ribofuranose), 5.18 (β-ribofuranose), 4.85 (β-ribopyranose), and 4.79 (α-ribopyranose). Upon the addition of 1 only the resonances corresponding to the ribofuranoses exhibit a downfield shift. This is expected as a result of cyclic boronate formation with ribofuranose (ref 3c).