Synthesis of stereoregular polygluconamides from D‐glucose and D‐glucosamine

Two stereoregular polygluconamides, one (3) of polypeptide‐type and the other (16) being a polycaproamide containing four stereocenters in the main chain of the repeating unit, have been prepared from D‐glucosamine and D‐glucose, respectively. The new polyamides were characterized by elemental analysis, and IR, 1H‐ and 13C‐NMR spectroscopies. The molecular weights for 3 and 16 were estimated as 25,000 and 67,000, respectively, on the basis of viscosimetric measurements. Both polyamides display high optical activity; they are highly hydrophilic and readily soluble in water as well as in a variety of organic solvents including chloroform. Polyamide 16 is highly crystalline and yields resistant films with spherulitic texture.