Synthesis and Ring Structure of 7-Acetamido-7-deoxy-L- galacto-heptulose

Abstract

7-Acetamido-7-deoxy-L-galacto-heptulose was prepared by oxidation of l-acetamido-l-deoxy-D-glycero-D-galacto-heptitol with Acetobacter suboxydans. The new acetamido-deoxy-L-heptulose was shown to be a pyranose by comparison with β-D-fructopyranose. The following equations represent the optical rotation of 7-acetamido-7-deoxy-α-L-galacto-heptulopyranose in water at 20 °C and 3.5 °C, respectively: ${\left[\alpha \right]}^{20}\text{D}=-15.5e^{-.0396t}-97.1,$ ${\left[\alpha \right]}^{3.5}\text{D}=-11.9e^{-.0101t}-105.8$ where t is the time in minutes after dissolution of the sample.