Effect of Fluorine Substituent on the Chitinase-catalyzed Polymerization of Sugar Oxazoline Derivatives

Abstract

Abstract 6-Deoxy-6-fluoro sugar oxazoline derivatives were synthesized and evaluated their polymerizabilities with the catalysis of chitinase. The polymerizability of an N-acetyl-6-deoxy-6-fluoroglucosamine oxazoline was lower than that of non-fluorinated N-acetylglucosamine oxazoline, only providing the ring-opened hydrolyzate. The disaccharide oxazoline derivative of N,N′-diacetyl-6′-deoxy-6′-fluorochitobiose exhibited lower polymerizability with the enzyme compared to that of the non-fluorinated N,N′-diacetylchitobiose oxazoline, providing the corresponding fluorinated chitin derivative in good yields within 4 h. These results suggest that the fluorine atom-incorporation reduced the reactivity of the oxazolines.